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Vacation Rentals and Cabins in Berkshires, MA

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    All 106 Rentals in Berkshires
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    $199
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    1 / 10
    5 of 5 stars (12) Excellent
    Great Barrington
    1 Bedroom / 1 Bathroom / Sleeps 3
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    $250
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    1 / 19
    5 of 5 stars (15) Excellent
    West Stockbridge
    5 Bedrooms / 2 Bathrooms / Sleeps 12
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    $350
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    1 / 21
    5 of 5 stars (5) Excellent
    Lee
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    $169
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    1 / 44
    5 of 5 stars (5) Excellent
    North Egremont
    1 Bedroom / 1 Bathroom / Sleeps 2
    travelers have booked this property
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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 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!
    5 of 5 stars Reviewed September 4, 2014
    Lovely haven in the bucolic Berkshire countryside . Our suite had everything we could want- privacy, beautiful restful decor, comfort , all in a gorgeous setting. Short drive to...
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    $130
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    1 / 10
    5 of 5 stars (1) Excellent
    North Adams
    2 Bedrooms / 1 Bathroom / Sleeps 8
    travelers have booked this property
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Mountain Views
    • Satellite TV
    • Wi-Fi
    • Deck
    • Stereo System
    • Shared Outdoor Pool...
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    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!!! Animals are welcome is needed. . The master bedroom has an... View all property information
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    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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    $249
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    1 / 19
    Hancock
    2 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Inquiry
    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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    $499
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    1 / 5
    5 of 5 stars (1) Excellent
    Hancock
    2 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Satellite TV
    • Mountain Views
    • Hot Tub
    • Game Room
    • Wi-Fi
    • Air Conditioning
    • Shared Indoor Pool
    • Staffed Property
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Fantastic Value at over 50% off the retail rates! Great Fall Season pricing of only $299 for each entire week's stay! No other fees due! We own this timeshare and can't use it this year! 2 bedroom, 2 bath, sleeps 8 Fully furnished with cooking utensils, linens and towels for up to 6 people.... View all property information
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    Hancock, Berkshires 01237
    5 of 5 stars Reviewed February 16, 2015
    Didn't go late enough for the Fall Foliage, but even as the leaves were just turning this was a lovely resort to visit. We go to the Highlands of Scotland every other year where...
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    $145
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    1 / 16
    5 of 5 stars (1) Excellent
    Hancock
    1 Bedroom / 1 Bathroom / Sleeps 6
    travelers have booked this property
    Overview Reviews (1) Make Inquiry
    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 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 / 19
    Stockbridge
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    Amenities & Details
    • 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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    Location Information
    Stockbridge, Berkshires 01262
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    $229
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    1 / 4
    4 of 5 stars (1) Very good
    Hancock
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    travelers have booked this property
    Overview Reviews (1) Make Inquiry
    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 / 36
    5 of 5 stars (114) Excellent
    Charlemont
    1 Bedroom / 1 Bathroom / Sleeps 4
    travelers have booked this property
    Overview Reviews (114) Make Inquiry
    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... View all property information
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    Charlemont, Berkshires 01339
    5 of 5 stars Reviewed June 25, 2015
    The cottage was the perfect little place for us and our fur babies to stay while visiting Eddie's Wheels. Great location, so peaceful among the beauty of nature. Very clean, close...
    5 of 5 stars Reviewed June 24, 2015
    This was a fantastic pet friendly accommodation. Our new dog Rusty had a wonderful time with Patricia's well behaved dogs. Patricia was kind enough to look in on him and helped to...
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    $499
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    1 / 32
    5 of 5 stars (2) Excellent
    Stockbridge
    4 Bedrooms / 4 Bathrooms / Sleeps 12
    travelers have booked this property
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    Amenities & Details
    • Private Fishing...
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Stereo System
    • Sauna
    • Mountain Views
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    We call this house ‘South Sedgwick’ because of its location on a piece of land formerly used by the Sedgwick family for picnicking–an ideal spot for relaxation with stunning views of Monument Mountain and Ice Glen. The house is newly constructed with ash hardwood floors, custom white pine trim and... View all property information
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    Location Information
    Stockbridge, Berkshires 01262
    5 of 5 stars Reviewed December 3, 2014
    What a great place! Teva was wonderful to work with, communication was incredible, and he is very welcoming. The house was spacious, very comfortable with 9 people! Teva came by...
    5 of 5 stars Reviewed July 18, 2014
    Our family of 5 rented this home over July 4th weekend and we couldn't have been more pleased. The home has just been newly renovated, is very tastefully appointed and looks and...
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    $275
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    1 / 32
    5 of 5 stars (1) Excellent
    Becket
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    travelers have booked this property
    Overview Reviews (1) Make Inquiry
    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 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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    $150
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    1 / 21
    5 of 5 stars (19) Excellent
    Lenox
    4 Bedrooms / 1 Bathroom / Sleeps 7
    travelers have booked this property
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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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    $1,600
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    1 / 10
    New Marlborough
    4 Bedrooms / 2 Bathrooms / Sleeps 6
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    Amenities & Details
    • Grill
    • Dryer
    • Central Heating
    • Wi-Fi
    • Washer
    • DVD Player
    • Refrigerator
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Welcome to Mill River, and our 1905 Queen Anne style Victorian backing onto hundreds of acres of woods, deep in the heart of the Berkshires. Step in and enjoy the peace of sitting on the porch of an old house on a quiet country lane, the wind in the trees and the babble of the nearby stream. The... View all property information
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    Location Information
    New Marlborough, Berkshires 01230
    From
    $300
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    1 / 25
    5 of 5 stars (2) Excellent
    Lee
    3 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Reviews (2) Make Inquiry
    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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    Location Information
    Lee, Berkshires 01238
    From
    $225
    / Night
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    1 / 16
    Hancock
    2 Bedrooms / 2 Bathrooms / Sleeps 8
    travelers have booked this property
    Overview Make Inquiry
    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
    From
    $250
    / Night
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    1 / 21
    Monterey
    5 Bedrooms / 3 Bathrooms / Sleeps 12
    Overview Make Inquiry
    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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    Monterey, Berkshires 01245
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    $250
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    1 / 5
    Granville
    5 Bedrooms / 3 Bathrooms / Sleeps 12
    travelers have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Water Views
    • TV
    • Waterfront
    • DVD Player
    • Balcony
    • Central Heating
    • Deck
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    4 Bedrooms, 3 Baths, 3 Guest Rooms, Open Floor Plan Kitchen, Living, Dining 4 Bedrooms, 3 Baths, 3 Guest Rooms, Open Floor Plan Kitchen, Living, Dining Lakefront, 4 bedrooms, 3 baths, 3 guest rooms, open floor plan with kitchen, living and dining areas, family room, sports room, deck, two... View all property information
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    Granville, Berkshires 01034
    From
    $375
    / Night
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    1 / 10
    Sheffield
    3 Bedrooms / 6 Bathrooms / Sleeps 8
    Overview Make Inquiry
    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
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    $70
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    1 / 6
    North Adams
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Inquiry
    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 is walking distance to Mass MoCA and minutes from downtown Williamstown and/or downtown North Adams. The... View all property information
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    Location Information
    North Adams, Berkshires 01247
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    $250
    / Night
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    1 / 16
    5 of 5 stars (1) Excellent
    North Adams
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    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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    $150
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    1 / 16
    4.5 of 5 stars (2) Very good
    Stockbridge
    1 Bedroom / 1 Bathroom / Sleeps 4
    travelers have booked this property
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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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    Location Information
    Stockbridge, Berkshires 01262
    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...
    5 of 5 stars Reviewed May 29, 2015
    Stayed 3 nights in the one-bedroom apartment connected to the main house. The apartment was very private, well kept and well appointed. Very quiet also. Owners were very...
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    $900
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    1 / 12
    South Lee
    1 Bedroom / 2 Bathrooms / Sleeps 4
    traveler have booked this property
    Overview Make Inquiry
    Amenities & Details
    • TV
    • Internet Access
    • Playground
    • Mountain Views
    • Deck
    • Shared Indoor Pool
    • Hot Tub
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    RIght off the Mass Pike Exit 2, Berkshire family vacation condo with full kitchen and all amenities.Take in Boston Symphony at Tanglewood and dance at Jacob's Pillow, theatre at Shakespeare & Company, Yoga at Kripalu, a spa day at Canyon Ranch, the Norman Rockwell Museum, Hancock Shaker Village,... View all property information
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    Location Information
    South Lee, Berkshires 01260
    From
    $300
    / Night
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    1 / 10
    West Stockbridge
    5 Bedrooms / 2 Bathrooms / Sleeps 12
    Overview Make Inquiry
    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
    $500
    / Night
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    1 / 15
    Tyringham
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    traveler have booked this property
    Overview Make Inquiry
    Amenities & Details
    • 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
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    $225
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    Tyringham
    1 Bedroom / 1 Bathroom / Sleeps 2
    traveler have booked this property
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    Amenities & Details
    • Refrigerator
    • Parking
    • Satellite TV
    • Linens Provided
    • Internet Access
    • DVD Player
    • Balcony
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Charming, One Bedroom Cottage, former sculpting studio on the Santarella Estate in Tyringham, MA. Known as the 'Silo Studio', there is a bedroom with queen bed upstairs, sitting room, wet bar with Micro/Fridge and bath downstairs. Fall asleep to sounds of babbling brook and views to pond and forest... View all property information
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    Tyringham, Berkshires 01264
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    $225
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    Stockbridge
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    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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    Location Information
    Stockbridge, Berkshires 01262
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    $750
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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
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    $375
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    1 / 27
    3.5 of 5 stars (2) Average
    Great Barrington
    5 Bedrooms / 4 Bathrooms / Sleeps 10
    travelers have booked this property
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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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    Location Information
    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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    $360
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    4 of 5 stars (8) Very good
    Lee
    5 Bedrooms / 3 Bathrooms / Sleeps 11
    travelers have booked this property
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    Amenities & Details
    • Satellite TV
    • Central Heating
    • DVD Player
    • Deck
    • Stereo System
    • Washer
    • Dryer
    • Internet Access
    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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    $125
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    5 of 5 stars (2) Excellent
    West Stockbridge
    2 Bedrooms / 1 Bathroom / Sleeps 6
    travelers have booked this property
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    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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    $150
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    5 of 5 stars (4) Excellent
    Richmond
    3 Bedrooms / 1 Bathroom / Sleeps 6
    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
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    $225
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    5 of 5 stars (4) Excellent
    Stockbridge
    3 Bedrooms / 2 Bathrooms / Sleeps 7
    travelers have booked this property
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    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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    Location Information
    Stockbridge, Berkshires 01262
    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...
    5 of 5 stars Reviewed September 30, 2013
    We rented this cabin originally for 5: 2 adults and 3 children (6,11,13). At the last minute our older daughter (18) decided to join us. The cabin is very spacious and...
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    $259
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    1 / 27
    Tyringham
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Inquiry
    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
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    $200
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    3 of 5 stars (1) Average
    Stockbridge
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    travelers have booked this property
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    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
    3 of 5 stars Reviewed July 30, 2014
    Nice house but tired bathrooms and kitchen. One great bedroom, two so so. Hot one nite and needed non existing a/c. Great screened porch with view of water. Canoe was a plus...
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    $500
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    Hinsdale
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    travelers have booked this property
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    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
    $300
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    Great Barrington
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    traveler have booked this property
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    Amenities & Details
    • Air Conditioning
    • Washer
    • DVD Player
    • Mountain Views
    • Stereo System
    • Internet Access
    • Fireplace
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Beautifully furnished, updated 3,000 square foot house. 3 bedrooms, 2 full baths; large sun room with great windows and sky-lights, comfortable seating area for 6 plus cafe table; dining room with table for 6 to 8 people; reading room with a wood-burning stove; living room with a fireplace;... View all property information
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    Location Information
    Great Barrington, Berkshires 01230
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    $175
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    4.5 of 5 stars (13) Very good
    Monterey
    3 Bedrooms / 2 Bathrooms / Sleeps 7
    traveler have booked this property
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    Amenities & Details
    • Mountain Views
    • Playground
    • Water Views
    • Satellite TV
    • Internet Access
    • Waterfront
    • Hot Tub
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Charming house with the feeling of a cottage, set on a knoll with adjacent cathedral-like pine forest. ** Stone fireplace, woodstove, beautiful kitchen with modern appliances (gas stove, microwave, refrigerator with water/ice dispenser, dishwasher, breadmaker, crockpot, blender, etc.) **... View all property information
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    Monterey, Berkshires 01245 0933
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    $525
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    5 of 5 stars (16) Excellent
    Sheffield
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (16) Make Inquiry
    Amenities & Details
    • Satellite TV
    • Internet Access
    • Deck
    • DVD Player
    • Stereo System
    • Mountain Views
    • Hot Tub
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Enjoy your vacation in a beautiful historic house located in the heart of the Berkshires. Located two and a quarter hours north of New York City, this circa-1770s center chimney colonial will charm and delight your family and guests. 88 acres of land with views of Mt. Washington and Mount Everett... View all property information
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    Sheffield, Berkshires 01257
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    $400
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    Lenox
    4 Bedrooms / 2 Bathrooms / Sleeps 10
    traveler have 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
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    1 / 22
    Great Barrington
    4 Bedrooms / 6 Bathrooms / Sleeps 12
    Overview Make Inquiry
    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
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    $200
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    Great Barrington
    2 Bedrooms / 1 Bathroom / Sleeps 4
    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
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    $150
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    5 of 5 stars (5) Excellent
    North Adams
    2 Bedrooms / 1 Bathroom / Sleeps 5
    traveler have booked this property
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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 17, 2013
    We chose to rent a house because we wanted space for our 2 teenagers. This place was perfect: room for all, but neat and cozy. Most places we've rented with kitchens are...
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    $139
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    5 of 5 stars (9) Excellent
    Becket
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    travelers have booked this property
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    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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    $450
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    5 of 5 stars (1) Excellent
    Lee
    1 Bedroom / 1 Bathroom / Sleeps 2
    traveler have booked this property
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    Amenities & Details
    • Central Heating
    • Fireplace
    • Internet Access
    • Washer
    • Mountain Views
    • Hot Tub
    • Dryer
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    handsome and welcoming, this authentic Berkshire lodge will make you feel like you`re in an old fashioned Christmas card! fireplace blazing, wood floors post and beam, hand planed planks. in the kitchen the floor is marble slabs from the famous lee marble quarry. Daniel Chester French, the designer... View all property information
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    Location Information
    Lee, Berkshires 01238
    5 of 5 stars Reviewed June 12, 2014
    I had several summer months here, it never disappoints. Full of nature's bounty, hospitable host, friendly vacationers. Very close to all the best of the Berkshires, Tanglewood...
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    $350
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    5 of 5 stars (1) Excellent
    Great Barrington
    4 Bedrooms / 2 Bathrooms / Sleeps 9
    travelers have booked this property
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    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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    5 of 5 stars (1) Excellent
    Pittsfield
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    travelers have booked this property
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    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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    5 of 5 stars (1) Excellent
    Lee
    1 Bedroom / 1 Bathroom / Sleeps 2
    traveler have booked this property
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    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    first floor queensized bed, bath with shower. floors are wood ceiling has exposed beams and is furnished with oak antiques and a big wingbacked chair.built in bookshelf was from a companionway on a wooden sailing vessel owned by a sea captain that owned and ran the lodge back at the turn of the... View all property information
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    Lee, Berkshires 01238
    5 of 5 stars Reviewed June 17, 2014
    And I hope to stay here again in the future. I feel very comfortable here - good privacy, the house is huge, rustic charm, generally very quiet. The property is massive - and the...
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    $175
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    5 of 5 stars (12) Excellent
    Lanesboro
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travelers have booked this property
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    Amenities & Details
    • Playground
    • Central Heating
    • Refrigerator
    • DVD Player
    • Stove
    • Grill
    • Internet Access
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    If you’ve driven by, you’ve wondered about the story of this beautiful stone building. Built in 1832 as a one-room schoolhouse – a function it served until 1950 -- this charming and historic building has been given new life as a vacation getaway. It is perfect for romantic weekends or family... View all property information
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    Location Information
    Lanesboro, Berkshires 01237
    5 of 5 stars Reviewed July 7, 2014
    We were lucky to happen upon this gem, and highly recommend it to families visiting the area of Mt. Greylock. Great on a rainy day, and interesting for all given the history of...
    5 of 5 stars Reviewed May 30, 2014
    We have stayed in several vacation rentals, and this one was extremely charming. The very first time I saw this one I just knew we had to vacation here while we were in The...
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