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Vacation Rentals and Cabins in Berkshires, MA

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    1 / 5
    5 of 5 stars (1) Excellent
    Granville
    5 Bedrooms, 3 Bathrooms, Sleeps 12
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    1 / 22
    5 of 5 stars (9) Excellent
    Lee
    4 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 / 32
    5 of 5 stars (2) Excellent
    Stockbridge
    4 Bedrooms, 4 Bathrooms, Sleeps 12
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    1 / 19
    5 of 5 stars (15) Excellent
    West Stockbridge
    5 Bedrooms, 2 Bathrooms, Sleeps 12
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    Amenities & Details
    • Central Heating
    • Horse Riding Nearby
    • Internet Access
    • There Are Tennis...
    • Satellite TV
    • DVD Player
    • Mountain Views
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Quaint, , 2 story 1850's farmhouse in the Berkshires with original ceiling beams and 16' floor boards in much of the house. Fully furnished with 5 bedrooms, 2 full baths and a gorgeous screened-in porch overlooking 4 acres of gardens, stream and wooded mountains. Country kitchen with dish washer,... View all property information
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    West Stockbridge, Berkshires 01266
    5 of 5 stars Reviewed June 11, 2015
    This beautiful farmhouse is perfect for friends and families who want an affordable Berkshire getaway with easy access to all the local attractions. I especially loved the long...
    5 of 5 stars Reviewed May 20, 2015
    We came from all over the northeast for a family get together, and were thrilled with the house. Plenty of room, clean and nicely decorated, close to all the Berkshires have to...
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    1 / 7
    5 of 5 stars (8) Excellent
    North Adams
    2 Bedrooms, 1 Bathroom, Sleeps 4
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    Amenities & Details
    • Deck
    • Grill
    • Porch
    • DVD Player
    • Fireplace
    • Refrigerator
    • TV
    • Housekeeping...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Cozy cottage with complete privacy on 142 acres and borders Monroe State Forest. Cottage offers 2 bedrooms, 1 bathroom, large living room, eat in kitchen, deck with grill, TV and DVD. Hiking and biking is available right outside your door. The Dunbar Brook Trail boasts great hiking and a grove of... View all property information
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    North Adams, Berkshires 01247
    5 of 5 stars Reviewed August 25, 2015
    Descriptions are accurate. The house and grounds are very well kept. Extremely clean especially bathroom and kitchen. It is located at the end of a hard pack dirt road with no...
    5 of 5 stars Reviewed August 24, 2015
    The minute we entered the cottage we felt at home. A perfect secluded, warm and cosy getaway. Our only sorrow was that we could only stay for one night. We prepared dinner in the...
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    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 8
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    • Horse Riding Nearby
    • Washer
    • Central Heating
    • Dryer
    • Stove
    • Housekeeping...
    • Wi-Fi
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Our 1762 Farmhouse is lovingly being restored with gardens in the Berkshires. Mission statement: Educating members in life, farming, and creative art skills acknowledging God as our provider. One mile from the Norman Rockwell Museum and 5 miles from Tanglewood. Come join the farm 'Agritourism'... View all property information
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    Stockbridge, Berkshires 01262
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    1 / 32
    5 of 5 stars (2) Excellent
    Becket
    4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Come to the Berkshires and stay in one of the most beloved areas of Massachusetts. We are located close to Lenox, Stockbridge, Lee, Great Barrington and more. Our 3400 square foot ranch home is located in the heart of the Berkshires awaiting memorable times with your family and friends. Our... View all property information
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    Becket, Berkshires 01223
    5 of 5 stars Reviewed August 19, 2015
    Amazing place for its location, layout, and superb owner! 1. The location is ideal. It's under 3 miles to Jacobs Pillow Dance, about 25 minutes to Tanglewood, 12 minutes form...
    5 of 5 stars Reviewed August 29, 2014
    This was our first trip to the Berkshires and we feel fortunate to have found this fabulous home. It suited our needs perfectly as we were traveling with kids and grandparents...
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    1 / 50
    5 of 5 stars (6) Excellent
    North Egremont
    1 Bedroom, 1 Bathroom, Sleeps 2
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    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Mountain Views
    • Waterfront
    • Satellite TV
    • Water Views
    • Air Conditioning
    • Private Fishing...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Located in the Berkshire mountains on more than 5 acres surrounded by 29 acres of conservation land. Featuring beautiful views of meadows, mountains and farm land bordering the crystal clear Green River (great trout fishing).Only 10 minutes from Great Barrington's Main Street stores, resturaunts,... View all property information
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    North Egremont, Berkshires 01230
    5 of 5 stars Reviewed July 8, 2015
    This suite is located in a beautiful serene setting. Barbara keeps the suite very clean, and her attention to every detail is unmatched. We had a wonderful stay, and only wish...
    5 of 5 stars Reviewed September 11, 2014
    I had a wonderful stay! The property is gorgeous and serene. The suite is clean, very nicely decorated and private. Absolutely lovely!
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    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Overview
    Amenities & Details
    • Sauna
    • Hot Tub
    • Fireplace
    • Game Room
    • Pool Table
    • Washer
    • Mountain Views
    • Shared Indoor Pool
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Ski-In/Ski-Out Plus Year-Round Mountainside Fun. Wyndham Bentley Brook is situated right at the base of Jiminy Peak ski mountain, making this resort an exceptional choice for mountainside play. In winter, ski out your door and onto the lifts; in spring, summer and fall, enjoy hiking and horseback... View all property information
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    Hancock, Berkshires 01237
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    $145
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    1 / 16
    5 of 5 stars (2) Excellent
    Hancock
    1 Bedroom, 1 Bathroom, Sleeps 6
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    Amenities & Details
    • Mountain Views
    • Stereo System
    • Internet Access
    • Deck
    • Satellite TV
    • Fireplace
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Low long term rates. Call $2500/mo for 3 months. Free Electric Vehicle Charging Station! (240V 40A no J1772) Thanksgiving Special - Nov 24 - Dec 1 - $500 Christmas Special - Dec 20 - Dec 27 - $800 Ski Season Dec 1 - Mar 31 $8000 April $50/nt Summer Cultural May 26, 2014 - Seot 2, 2014 $7500 Summer... View all property information
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    Hancock, Berkshires 01237
    5 of 5 stars Reviewed July 30, 2015
    This is a lovely rental in the heart of the Berkshires. Each morning you wake up to a view of Jiminy Peak and the sounds of bird life. Tom and Susan are wonderful innkeepers and...
    5 of 5 stars Reviewed October 16, 2014
    This property is perfect for people with pets. Serene setting with a gorgeous view. The hosts, Tom and Susan, were gracious and very helpful. Highly recommended if your travels...
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    1 / 4
    4 of 5 stars (1) Very good
    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Amenities & Details
    • Satellite TV
    • Mountain Views
    • Internet Access
    • DVD Player
    • Deck
    • Air Conditioning
    • Dryer
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Cozy ranch home 3 miles away from Jiminy Peak Ski Resort. Near MASS MOCA, Clark Art Institute, Williams College Contemperary Museum of Art, Williamstown Theatre Festival, Tanglewood, shopping, golf courses. Wrap around deck with beautiful mountain views. Family room with full wet bar & flat screen... View all property information
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    Hancock, Berkshires 01237
    4 of 5 stars Reviewed August 11, 2013
    Aside from the excessive amount of men's shirts in the closets (closets and drawers had not been emptied so storage space was minimal), the full trash bins and dirty dishes...
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    $120
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    1 / 37
    5 of 5 stars (121) Excellent
    Charlemont
    1 Bedroom, 1 Bathroom, Sleeps 4
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    Amenities & Details
    • Internet Access
    • Washer
    • Air Conditioning
    • Dryer
    • Satellite TV
    • Stereo System
    • Deck
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Discover Cavalier Cottage B&B, a pet-friendly home away from your home and an attractive alternative to conventional hotels, motels and B&B's. We warmly welcome visitors who come to this beautiful and diverse area of Western Massachusetts with or without their companion animals. Since opening the... View all property information
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    Charlemont, Berkshires 01339
    5 of 5 stars Reviewed August 20, 2015
    My husband and I and our dog really enjoyed out short stay and wish that it could have been longer. The warm, homemade warm scones that appeared each morning on the table on the...
    5 of 5 stars Reviewed August 10, 2015
    We had the pleasure of staying with at Cavalier Cottage last month and were thrilled with our accommodations and the wonderful care we received for our 2.5yrs old cavapoo, Felix...
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    1 / 16
    4.5 of 5 stars (3) Very good
    Stockbridge
    1 Bedroom, 1 Bathroom, Sleeps 4
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    Amenities & Details
    • TV
    • Refrigerator
    • Wi-Fi
    • Waterfront
    • Stove
    • Linens Provided
    • Patio
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    One bedroom air conditioned apartment with private entrance in 18th century house in Historic District of Stockbridge. Wonderful views of the river, 18th green of Stockbridge Golf Club and the Berkshire Hills. 5 minutes walk to the famous Red Lion Inn/town center. Self contained and private. You... View all property information
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    Stockbridge, Berkshires 01262
    5 of 5 stars Reviewed July 13, 2015
    I just got back from my weekend stay here last night, and if I hadn't been so tired, I would have posted this review already! I was absolutely thrilled with this rental - where...
    4 of 5 stars Reviewed June 21, 2015
    Lovely home, great location, walking distance to the town of Stockbridge. Many things to see and do while we stayed for our five day trip. Must see: Naumkeg, Shrine of Divine...
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    1 / 21
    5 of 5 stars (19) Excellent
    Lenox
    4 Bedrooms, 1 Bathroom, Sleeps 7
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    Amenities & Details
    • Dryer
    • Stereo System
    • Grill
    • Internet Access
    • Central Heating
    • Washer
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Located on a quiet side street in the charming Berkshire town of Lenox, Gartner House is a great place to call home while exploring this scenic, historical, and culturally rich area of Western Massachusetts. Walk to breakfast, lunch or dinner at one of the town's many charming restaurants, explore... View all property information
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    Lenox, Berkshires 01240
    5 of 5 stars Reviewed January 3, 2015
    Ski trip in Berkshires and this place was perfect. Gave us nice options to do on off days. Debra was great with any issues that came up and was very helpful and responsive...
    5 of 5 stars Reviewed October 22, 2014
    We spent the weekend at the Gartner House in Lenox to visit my son at Shakespeare and Company. From my first contact with Deb, she was friendly and helpful. It is evident...
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    $300
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    West Stockbridge
    5 Bedrooms, 2 Bathrooms, Sleeps 12
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Mountain Views
    • DVD Player
    • Ping Pong Table
    • Satellite TV
    • Wi-Fi
    • Game Room
    • Swingset
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Rent a comfortable 1840 farmhouse with 26 acres in the Berkshire mountains. Walk to the village of West Stockbridge or a short drive to all the Berkshire attractions. Close to the ski resorts of Butternut, Bousquet, Catamount and Jiminy Peak. The house sleeps 10 to 12 people and is fully equipped.... View all property information
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    Location Information
    West Stockbridge, Berkshires 01266
    From
    $225
    / Night
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    Hancock
    2 Bedrooms, 2 Bathrooms, Sleeps 8
    other travelers have booked this property
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Hot Tub
    • Sauna
    • Internet Access
    • Satellite TV
    • Shared Indoor Pool
    • Air Conditioning
    • Mountain Views
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Bentley Brook is a ski in/ski out resort located at the base of Jiminy Peak ski resort. On-site Amenities Include: Heated Indoor/Outdoor Pool (year round), 3 hot tubs, 'Get out & Play ' children's program, 3 tennis courts, game room, exercise equipment, sauna, theater with nightly movies.. At... View all property information
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    Hancock, Berkshires 01237
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    $225
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    Stockbridge
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Water Views
    • Fireplace
    • TV
    • Stereo System
    • Mountain Views
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This 1600 sq. ft. cottage boasts everything you would need for your visit to the Berkshires whether it be for a full summer / winter season to explore this beautiful area or a quick getaway to Tanglewood, The recently added master suite features a queen size bed, en-suite bathroom and a bonus... View all property information
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    Stockbridge, Berkshires 01262
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    $355
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    1 / 35
    4 of 5 stars (8) Very good
    Lee
    5 Bedrooms, 3 Bathrooms, Sleeps 11
    other travelers have booked this property
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    Amenities & Details
    • Mountain Views
    • Central Heating
    • Water Views
    • DVD Player
    • TV
    • Stereo System
    • Deck
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Beautiful house surrounded by protected woodland and a small beaver pond behind your backyard. All kinds of birds and wildlife. 5 Bedrooms, 2.5 baths, brand new kitchen, open living/dining room, laundry room. Wood stove that can function as a fireplace. 3 heating zones for comfort. All new... View all property information
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    Lee, Berkshires 01238
    4 of 5 stars Reviewed September 27, 2014
    We went there for a golf buddy trip and it was the perfect place for us in the Berkshires. Place was very clean, and had all the comforts of home. Robin is super friendly and...
    5 of 5 stars Reviewed September 3, 2014
    This is a wonderful home! Robin has taken care with the furnishing and finishings, which are a nice blend of antique and modern. Her love of the home and region is apparent...
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    $199
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    1 / 10
    5 of 5 stars (15) Excellent
    Great Barrington
    1 Bedroom, 1 Bathroom, Sleeps 3
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    Amenities & Details
    • Boat Available
    • Satellite TV
    • Shared Outdoor Pool...
    • Stereo System
    • DVD Player
    • Central Heating
    • Mountain Views
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Berkshires: Romantic Berkshires Cottage with Stunning Views (Great Barrington) The Berkshires in spring, summer and fall are alive with beauty, and now is the time to plan your restoring getaway in this idyllic studio cottage with its glorious views of the rolling hills and verdant meadows..... View all property information
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    Great Barrington, Berkshires 01230
    5 of 5 stars Reviewed August 17, 2015
    We spent three nights at this lovely cottage, perfectly located a mere 7 minutes from town. The views from all windows are divine: mountains, rolling hills, endless big sky. We...
    5 of 5 stars Reviewed August 8, 2015
    This lovely spot was perfect for the two of us during our week in the Berkshires. Great Barrington is a beautiful town, well situated near great theater, music, dance...
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    $299
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    Lee
    2 Bedrooms, 1 Bathroom, Sleeps 4
    Overview Make Inquiry
    Overview
    Amenities & Details
    • There Are Tennis...
    • Air Conditioning
    • Watersports Nearby
    • Deck
    • TV
    • Washer
    • DVD Player
    • Boat Available
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Located in the tranquil hills of the beautiful Berkshires. This truly is a wooded wonderland filled with restful beauty and abundant wildlife. Wonderful retreat in the Berkshires. Private and secluded. Minutes from Tanglewood, The Red Lion Inn and The Norman Rockwell museum. Skiing. Private lake... View all property information
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    Location Information
    Lee, Berkshires 01238
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    1 / 25
    5 of 5 stars (2) Excellent
    Lee
    3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Amenities & Details
    • Fireplace
    • DVD Player
    • Satellite TV
    • Stereo System
    • Hot Tub
    • Internet Access
    • Deck
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    ** Rental is only available for 2 week minimum during the summer (July - August) Special Summer Deal -- Rent for the Season (July and August) and get either the last week in June OR the first week in September for half price! This adorable cottage has all the ingredients for the ultimate retreat... View all property information
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    Lee, Berkshires 01238
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    $250
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    1 / 16
    5 of 5 stars (1) Excellent
    North Adams
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    other travelers have booked this property
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    Amenities & Details
    • Central Heating
    • TV
    • Waterfront
    • Mountain Views
    • Deck
    • Private Fishing...
    • Boat Available
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Windsor Cottage is a beautiful, newly renovated lakeside retreat located on Windsor Lake in North Adams, MA. where you can enjoy your own private water access from your front lawn. You will feel like you are in the middle of the forest, yet you are in walking distance to the town, Mass MoCA and... View all property information
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    North Adams, Berkshires 01247
    5 of 5 stars Reviewed August 16, 2014
    The cottage is well located, seemingly remote, but with nearby access to local attractions and restaurants. I enjoyed sitting on the deck, looking out over the water in the...
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    1 / 27
    3.5 of 5 stars (2) Average
    Great Barrington
    5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Amenities & Details
    • Deck
    • Stereo System
    • Air Conditioning
    • Satellite TV
    • Mountain Views
    • DVD Player
    • Grill
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Shaker Hill is a quirky rambling farmhouse located less than 3 hours from NYC and Boston. Hidden away down a 400’ unpaved driveway on 30 acres of fields and forest in the heart of the Berkshires, Shaker Hill is totally private and surrounded by 30 acres of rolling fields, diverse wetlands,... View all property information
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    Great Barrington, Berkshires 01230
    3 of 5 stars Reviewed September 11, 2014
    This is a very large house, more than adequate in size for a group of ten people. It has a big yard and a spectacular view of the mountains, especially from an upstairs window...
    4 of 5 stars Reviewed January 4, 2015
    MAにあるSki Butternut というスキー場を利用するため、クリスマスからお正月にかけて、6泊7日で滞在しました。4家族(大人7人、子供5人・子供は5歳と7歳)というグループでしたが部屋の広さは十分で、非常に快適に過ごすことができました。 【ロケーション】 Butternut...
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    $500
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    Hinsdale
    4 Bedrooms, 3 Bathrooms, Sleeps 8
    other travelers have booked this property
    Overview Make Inquiry
    Overview
    Amenities & Details
    • DVD Player
    • Water Views
    • Washer
    • Deck
    • Dryer
    • TV
    • Central Heating
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    The best place in the world to watch the sunset! Set up high on a hill and nestled amidst the pine trees, this four year old, private and spacious contemporary home overlooks Lake Ashmere (across the road) in Hindsdale. The great room with cathedral ceilings and a wall of windows overlooking the... View all property information
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    Location Information
    Hinsdale, Berkshires 01235
    From
    $250
    / Night
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    1 / 10
    5 of 5 stars (2) Excellent
    Great Barrington
    2 Bedrooms, 1 Bathroom, Sleeps 5
    other travelers have booked this property
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    Overview Reviews (2)
    Amenities & Details
    • Air Conditioning
    • Fireplace
    • Internet Access
    • Mountain Views
    • DVD Player
    • Stereo System
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Please note that this property is not winterized so it's not available this winter of 2012. I am winterizing this spring & the property will be available on a year around basis stating on 5/15/2013. Please go to VRBO.com listing #219964 to see my reviews, I am new to flipkey. Located in South... View all property information
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    Location Information
    Great Barrington, Berkshires 33304
    5 of 5 stars Reviewed May 20, 2013
    This was a perfect weekend for us. I am very picking when choosing a cabin rental because I want it to be "just right--" to fit into all of my ideal visions of the quintessential...
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    $250
    / Night
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    Tyringham
    1 Bedroom, 1 Bathroom, Sleeps 4
    Overview Make Inquiry
    Overview
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Santarella Estate and Gardens in Tyringham, MA is a magical destination in the heart of one of the Berkshires' most beautiful valleys, located 3 miles from Interstate 90 and 15 minutes from most of the principal attractions (Tanglewood, Jacob's Pillow, Norman Rockwell museum, etc.) Pictures are... View all property information
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    Location Information
    Tyringham, Berkshires 01264
    From
    $275
    / Night
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    Monterey
    5 Bedrooms, 3 Bathrooms, Sleeps 12
    other traveler has booked this property
    Overview Make Inquiry
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    Amenities & Details
    • Mountain Views
    • Water Park Nearby
    • Central Heating
    • Watersports Nearby
    • TV
    • DVD Player
    • Playground
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This is a beautiful Berkshire, post and beam private house nestled in the woods just off the Appalachian trail. Set on one of the Berkshires most coveted roads close to fresh water swimming in Lake Garfield, boating, fishing, classical outdoor concerts at Tanglewood & Skiing are all close by. The... View all property information
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    Location Information
    Monterey, Berkshires 01245
    From
    $500
    / Night
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    Tyringham
    4 Bedrooms, 2 Bathrooms, Sleeps 8
    other traveler has booked this property
    Overview Make Inquiry
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    • Central Heating
    • Satellite TV
    • Staffed Property
    • Wi-Fi
    • DVD Player
    • Watersports Nearby
    • Mountain Views
    • Fireplace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Located on the Santarella Estate, an historic site located in the the Massachussetts' Berkshires. The colonial home is the former residence of sculptor Sir Henry Hudson Kitson. The estate includes the landmark, iconic storybook style 'Gingerbread House,' designed by Kitson to look like an English... View all property information
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    Location Information
    Tyringham, Berkshires 01264
    From
    $750
    / Night
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    Lee
    5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    --Brand new 3400 sq ft Lee home in a private lake community, Berkshires --Situated on 4 wooded acres on a quiet country road --Pristine home features two master bedroom suites plus 3 additional bedrooms, 5 bathrooms --Spacious living room with vaulted ceiling & skylights --Fully equipped kitchen,... View all property information
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    Location Information
    Lee, Berkshires 01238
    From
    $139
    / Night
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    1 / 16
    5 of 5 stars (9) Excellent
    Becket
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    other travelers have booked this property
    Overview Reviews (9) Make Inquiry
    Overview Reviews (9)
    Amenities & Details
    • Air Conditioning
    • Boat Available
    • Waterfront
    • Stereo System
    • Satellite TV
    • Water Views
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Pretty cottage in the woods on a beautiful private lake with a stream running through the property's two acres of land. Newly constructed, spacious and sunny second floor with views of the lake. Hardwood floors throughout the house. Swim, kayak, canoe or fish from the back yard, or just lounge... View all property information
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    Becket, Berkshires 01223
    5 of 5 stars Reviewed January 17, 2014
    We had a wonderful time in the Berkshires, and this cottage was the central part of our weekend. The house was superb and extra clean, with everything provided. Views were...
    5 of 5 stars Reviewed October 1, 2013
    Excellent spot for a quiet retreat. Located on a nice pond with just a few neighbors we never even saw or heard. The cottage has all the essentials. Very clean and inviting...
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    $67
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    Lee
    1 Bedroom, 1 Bathroom, Sleeps 1
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    Overview
    Amenities & Details
    • Patio
    • Wi-Fi
    • Refrigerator
    • There Are Tennis...
    • Satellite TV
    • Central Heating
    • Dryer
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Share a beautifully renovated Victorian home, in downtown Lee, Ma, right in the heart of the Berkshires. Walking distance to town, and on the bus line. Wifi, cable TV, off street parking. Shared kitchen and bath. I have two cats and one other housemate. I am a gospel and blues musician. This is a... View all property information
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    Location Information
    Lee, Berkshires 01238
    From
    $225
    / Night
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    1 / 16
    5 of 5 stars (5) Excellent
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 7
    other travelers have booked this property
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    Overview Reviews (5)
    Amenities & Details
    • Boat Available
    • There Are Tennis...
    • Watersports Nearby
    • Fireplace
    • Satellite TV
    • Washer
    • Internet Access
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located a short walk to the town beach on the Stockbridge Bowl, and 1.5 miles from Tanglewood's Hawthorn entrance, this casual summer cottage is a great get away for the whole family. The master bedroom is equipped with a queen bed; two twins in the 2nd bedroom, and a full-size bed in the 3rd... View all property information
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    Stockbridge, Berkshires 01262
    5 of 5 stars Reviewed July 31, 2015
    This was a wonderful place to spend a family vacation. The house is immaculate, functional and well furnished. The proximity to all of the many venues and activities the area...
    4 of 5 stars Reviewed October 24, 2013
    Some friends and I wanted to have a reunion as we are spread out along the east coast, and we were debating between camping or renting. I heard no end of the gratitude from my...
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    $125
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    1 / 8
    5 of 5 stars (2) Excellent
    West Stockbridge
    2 Bedrooms, 1 Bathroom, Sleeps 6
    other travelers have booked this property
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    Overview Reviews (2)
    Amenities & Details
    • Air Conditioning
    • Fireplace
    • Washer
    • Refrigerator
    • Dryer
    • Satellite TV
    • Internet Access
    • Stove
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Cozy and modern two bedroom and one bath vacation home with lake nearby Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This luxury home can sleep up to 6 people and has lake access nearby. Enjoy a nice cup of hot chocolate by the fireplace in the living... View all property information
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    Location Information
    West Stockbridge, Berkshires 01266
    5 of 5 stars Reviewed December 18, 2013
    We stayed at this home in Housatonic, which is part of Great Barrington, the Smithsonian pic for best small town in the USA. I hope you all don't however as one of the best...
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    $250
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    1 / 14
    5 of 5 stars (5) Excellent
    West Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 7
    other travelers have booked this property
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    Amenities & Details
    • Private Fishing...
    • Internet Access
    • Washer
    • Deck
    • Fireplace
    • Mountain Views
    • Dryer
    • Central Heating
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located in West Stockbridge minutes from everything . Nestled in the Berkshire Mountains. Convenient yet Private Visit our web-site ataberkshirehomeThe Berkshires is a world unto itself. It is scenic beauty married to cultural bounty. It is urban sophistication in an idyllic, rural setting. It is... View all property information
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    Location Information
    West Stockbridge, Berkshires 01266
    5 of 5 stars Reviewed November 2, 2014
    Had an outstanding couple of weeks staying here; place was quiet, peaceful and not too far from civilization. All the amenities and space you could wish for and Cassandra and her...
    5 of 5 stars Reviewed August 25, 2014
    We were excited to get away from NYC and stay in the Berkshires! It was a wonderful stay at this home! So spacious, comfortable, lots of thoughtful gestures for our stay! We...
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    $375
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    1 / 10
    5 of 5 stars (2) Excellent
    Sheffield
    3 Bedrooms, 6 Bathrooms, Sleeps 8
    Overview Reviews (2) Make Inquiry
    Overview Reviews (2)
    Amenities & Details
    • Air Conditioning
    • Watersports Nearby
    • Housekeeping...
    • Hot Tub
    • TV
    • There Are Tennis...
    • Mountain Views
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Charmingly restored 1840 cottage in the apple orchard of a working organic farm. Completely renovated in 2015 with thoughtful amenities, fresh eggs and produce and acres of trails and views. Close to waterfalls and lakes. Nearby ski hills, Tanglewood concerts, theatre, film festival, dance and... View all property information
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    Sheffield, Berkshires 01257
    5 of 5 stars Reviewed July 24, 2015
    New England working farm. Lovely setting Great hospitality. Easy access to Tanglewood and other Berkshire attractions.
    5 of 5 stars Reviewed July 22, 2015
    What a beautifully decorated and comfortable cottage! Incredible deck for long lazy summer afternoons. Property owners were wonderful ... friendly & helpful. Cannot wait to...
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    $2,450
    / Week
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    Great Barrington
    5 Bedrooms, 3 Bathrooms, Sleeps 10
    other traveler has booked this property
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    Overview
    Amenities & Details
    • Mountain Views
    • Deck
    • Satellite TV
    • Waterfront
    • Internet Access
    • DVD Player
    • Water Views
    • Boat Available
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Attractive year-round lakefront house in a wooded area on a pristine Round Pond in the Berkshires. Relax and enjoy the view from your deck or dock. Fish from the dock or take the boat out onto the lake. Ideal family retreat in Great Barrington and only a short drive to cultural attractions... View all property information
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    Location Information
    Great Barrington, Berkshires 01236
    From
    $400
    / Night
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    Lenox
    4 Bedrooms, 2 Bathrooms, Sleeps 10
    other traveler has booked this property
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    Amenities & Details
    • Sauna
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Playground
    • Shared Indoor Pool
    • Mountain Views
    • Shared Tennis Court
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    220+ Acres W\ Tennis Cts, Indoor / Outdoor Pool, Canoe, Fishing Boat, Hot Tub. New first time rental of 4 BR, 2BA, Cape Cod style, sleeps 10-12. New fully equipped kitchen w/ center island, indoor and outdoor barbecues, wine cooler, 2 fireplaces, large deck with 8 person hot tub and super seating... View all property information
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    Lenox, Berkshires 01240
    From
    $675
    / Night
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    Great Barrington
    4 Bedrooms, 6 Bathrooms, Sleeps 12
    Overview Make Inquiry
    Overview
    Amenities & Details
    • TV
    • Washer
    • Dryer
    • Internet Access
    • Air Conditioning
    • Fireplace
    • Grill
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This immaculate home is the place for relaxing, entertaining and sharing great times with family and friends. The house sets over 4 beautifully wooded acres. We call it the 'illision of seclusion,' as it is very private and yet is 5 minutes from the town as well as lakes, hiking, movies, theater,... View all property information
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    Location Information
    Great Barrington, Berkshires 01236
    From
    $200
    / Night
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    Great Barrington
    2 Bedrooms, 1 Bathroom, Sleeps 4
    other travelers have booked this property
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    Amenities & Details
    • DVD Player
    • Grill
    • Satellite TV
    • Linens Provided
    • Stove
    • Refrigerator
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Welcome to our School House Cottage located in the heart of the Berkshires. Set in front of the ledges of Warner Mountain, this historic home was originally a three room schoolhouse. An addition in the 1960's transformed it into a private home which it remained for many years. Now updated, the... View all property information
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    Location Information
    Great Barrington, Berkshires 01237
    From
    $259
    / Night
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    Tyringham
    3 Bedrooms, 3 Bathrooms, Sleeps 6
    Overview Make Inquiry
    Overview
    Amenities & Details
    • DVD Player
    • Deck
    • Dryer
    • Washer
    • Mountain Views
    • Central Heating
    • Wi-Fi
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This turn of the century cottage is located on a 130 acre property, and is stocked with linens. Three and a half baths, three full bedrooms, kitchen, living room, dining room, screened porches, a deck, and washer dryer. The house is across the brook and up a stone staircase (30 steps) from the... View all property information
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    Location Information
    Tyringham, Berkshires 01264
    From
    $150
    / Night
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    1 / 11
    5 of 5 stars (4) Excellent
    Richmond
    3 Bedrooms, 1 Bathroom, Sleeps 6
    other travelers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Water Views
    • Washer
    • Satellite TV
    • DVD Player
    • Internet Access
    • Playground
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Fantastic spot for families and for those looking for a quiet getaway. Come have some summer fun, enjoy the autumn colors or play in the snow. This year round cottage is the perfect spot for those who enjoy outdoor activities. The house is on a private dead end road, has a wonderful lake view... View all property information
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    Location Information
    Richmond, Berkshires 01254
    From
    $350
    / Night
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    1 / 11
    5 of 5 stars (1) Excellent
    Great Barrington
    4 Bedrooms, 2 Bathrooms, Sleeps 9
    other travelers have booked this property
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    Overview Reviews (1)
    Amenities & Details
    • Hot Tub
    • Washer
    • Internet Access
    • Satellite TV
    • Stereo System
    • Fireplace
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    The perfect house for friends and family to share! Bright,uncluttered, and inviting, with privacy and views just minutes to town. There are two fireplaces,a sunken living room, dining room with seating for 10, 4 bedrooms, 2 full bathrooms, and a cozy hang out area in the basement. There is a washer... View all property information
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    Location Information
    Great Barrington, Berkshires 01230
    5 of 5 stars Reviewed February 5, 2015
    This was the first time we had a rental cottage, but it surpassed all of our expectations. The cottage was clean and well arranged. Kitchen was spacious enough for more than a few...
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    $150
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    1 / 20
    5 of 5 stars (1) Excellent
    Pittsfield
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    other travelers have booked this property
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    Amenities & Details
    • Waterfront
    • Fireplace
    • Stereo System
    • Satellite TV
    • Air Conditioning
    • Mountain Views
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    House is very private and located on 4 acres of Land. Back yard is peaceful and overlooks ponds. The backyard has a patio/picnic area with gas grill and firepit. One of the ponds has a spurting and lighted fountain that is relaxing ...so have a campfire at night and watch the lighted fountain for a... View all property information
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    Pittsfield, Berkshires 01201
    5 of 5 stars Reviewed November 29, 2014
    The photos speak for themselves. Overall, the home was a great escape from city life, and included its own scenery and lake. My only complaint is that our stay was so short-lived...
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    $225
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    1 / 11
    3.5 of 5 stars (3) Average
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    other travelers have booked this property
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    Overview Reviews (3)
    Amenities & Details
    • Stereo System
    • Central Heating
    • Internet Access
    • DVD Player
    • Satellite TV
    • Mountain Views
    • Waterfront
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    3-bedroom home on lake, near Tanglewood. 2 baths, den, screened porch, large yard. View all property information
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    Location Information
    Stockbridge, Berkshires 01262
    4 of 5 stars Reviewed July 14, 2015
    Those who used the cottage this week ranged from me alone to one night with eight people for one night. Sleeping was not a problem. The house is ideally located between Lenox...
    3 of 5 stars Reviewed July 4, 2015
    On the water with canoes, close to Tanglewood, but tired amenities. Poor second bedroom, not yet cleaned until after we arrived, but most unfortunate it was a very hot weekend...
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    From
    $140
    / Night
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    Hinsdale
    3 Bedrooms, 2 Bathrooms, Sleeps 7
    other travelers have booked this property
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Central Heating
    • TV
    • DVD Player
    • Stereo System
    • Internet Access
    • Deck
    • Washer
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Located on 19 acres of forest and a creek, mixing modern and traditional with a charming two story wall of windows overlooking a back deck. This comfortable furnished home has two bedrooms with an additional open loft area for a third bedroom, two baths, all hardwood floors, and contains a large... View all property information
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    Hinsdale, Berkshires 01235
    From
    $4,500
    / Week
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    Great Barrington
    6 Bedrooms, 6 Bathrooms, Sleeps 12
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Playground
    • Internet Access
    • Mountain Views
    • Fireplace
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This home is uniquely and magnificently furnished by a retired couple that spent 18 years traveling and living abroad. Even local real estate agents have called the house “special”. It has 7,000 sf of living space (3 floors) with plenty of places to be together or to be alone (as one so chooses).... View all property information
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    Location Information
    Great Barrington, Berkshires 01230
    From
    $130
    / Night
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    1 / 10
    5 of 5 stars (1) Excellent
    North Adams
    2 Bedrooms, 1 Bathroom, Sleeps 10
    other travelers have booked this property
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    Overview Reviews (1)
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Mountain Views
    • Watersports Nearby
    • Shared Outdoor Pool...
    • DVD Player
    • Water Park Nearby
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    I have a 2 to 3 bedroom first floor apartment located in a dead end street. This spacious 8 room apartment is surrounded by woods and minutes from downtown North Adams or Williamstown!! It is also walking distance to Mass MoCa (about a 10 minute walk)!!! Animals are welcome if needed. The master... View all property information
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    Location Information
    North Adams, Berkshires 01247
    5 of 5 stars Reviewed July 6, 2014
    Stephanie was helpful and accommodating of us and our last minute request . Sheafs it easy to stay, come and go and we found the location convenient yet private and remote from...
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    $70
    / Night
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    North Adams
    1 Bedroom, 1 Bathroom, Sleeps 2
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Wi-Fi
    • Housekeeping...
    • TV
    • Air Conditioning
    • DVD Player
    • Stereo System
    • Watersports Nearby
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • ?
    • x
    About this property
    I have a two bedroom apartment and I am renting out the spare bedroom. It is at the end of a dead end street with a huge wooded backyard that includes a grill, picnic table and two fire pits. It's walking distance to Mass MoCA and minutes from downtown Williamstown and/or downtown North Adams.... View all property information
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    Location Information
    North Adams, Berkshires 01247
    From
    $175
    / Night
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    1 / 2
    5 of 5 stars (1) Excellent
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 2
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Sunny, light , bright and wide! the queens room is one of the biggest rooms and has private ensuite bathroom with tub/shower. 2 big closets, large writing desk, comfy conversation area, 2 dressers full sized bed. a section of the room has original ceilings so persons taller than 6'2' would be... View all property information
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    Location Information
    Lee, Berkshires 01238
    5 of 5 stars Reviewed August 16, 2015
    I had the pleasure of staying at the Chestnut Lodge in the Queen's room. From the moment you step into the foyer you are taken back to a simpler time in this historic lodge. The...
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    From
    $200
    / Night
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    Savoy
    2 Bedrooms, 1 Bathroom, Sleeps 4
    other travelers have booked this property
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Grill
    • DVD Player
    • Internet Access
    • Fireplace
    • Refrigerator
    • Porch
    • Hot Tub
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located in a quiet corner of the northern Berkshires, this lovely two-bedroom home has a combined living room/kitchen with cathedral ceilings and a spacious bathroom complete with a 2-person jacuzzi tub. The house is located about a mile from beautiful Tannery Falls in the Savoy State Forest and... View all property information
    Make Inquiry
    Location Information
    Savoy, Berkshires 01256