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Vacation Rentals in Richmond, MA and nearby

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    All 65 Rentals in the Richmond Area
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    $150
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    1 / 11
    5 of 5 stars (4) Excellent
    Richmond
    3 Bedrooms / 1 Bathroom / Sleeps 6
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    $325
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    1 / 10
    Richmond
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    $450
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    1 / 20
    Richmond
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    The following rentals are within 10 miles of Richmond, Massachusetts.

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    1 / 19
    5 of 5 stars (15) Excellent
    West Stockbridge
    5 Bedrooms / 2 Bathrooms / Sleeps 12
    travelers have booked this property
    Overview Reviews (15) Make Inquiry
    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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    Location Information
    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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    $350
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    1 / 21
    5 of 5 stars (6) Excellent
    Lee
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    travelers have booked this property
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    Amenities & Details
    • Wi-Fi
    • Washer
    • DVD Player
    • Mountain Views
    • Air Conditioning
    • Fireplace
    • TV
    • Ping Pong Table
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Enjoy all the Berkshires has to offer in our new (2014) restoration and outstanding renovation of the historic South Lee Schoolhouse. Perched on a hillside just across the road from the Housatonic River and Beartown State Forest in the hamlet of South Lee, just outside of Stockbridge, the 1892... View all property information
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    Location Information
    Lee, Berkshires 01260
    5 of 5 stars Reviewed July 7, 2015
    We traveled with a group of 6 and this property was just perfect. Very open, spacious, modern and clean. The location was also very convenient to visiting the local attractions...
    5 of 5 stars Reviewed June 24, 2015
    My girlfriends and I make it a priority to get together each year and rent a vacation home. It was a unanimous consensus that Mary's home was our favorite stay place to date! It...
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    $130
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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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    $199
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    1 / 10
    5 of 5 stars (13) Excellent
    Great Barrington
    1 Bedroom / 1 Bathroom / Sleeps 3
    travelers have booked this property
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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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    Location Information
    Great Barrington, Berkshires 01230
    5 of 5 stars Reviewed June 27, 2015
    Magnificent view, hosts were lovely, very generous, the pool was divine. Can't give enough accolades-if you get a chance, don't walk-run there.
    5 of 5 stars Reviewed August 17, 2014
    We stayed at the cottage for three days, and it was just as lovely as advertised. The space is perfect for a couple, with a comfortable queen bed and well-equipped kitchen...
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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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    Location Information
    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 / 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
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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
    Overview Reviews (2) Make Inquiry
    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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    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
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    $150
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    1 / 16
    4.5 of 5 stars (3) Very good
    Stockbridge
    1 Bedroom / 1 Bathroom / Sleeps 4
    travelers have booked this property
    Overview Reviews (3) Make Inquiry
    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
    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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    $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
    Overview Reviews (2) Make Inquiry
    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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    $225
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    1 / 25
    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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    1 / 10
    5 of 5 stars (2) Excellent
    Great Barrington
    2 Bedrooms / 1 Bathroom / Sleeps 5
    travelers have booked this property
    Overview Reviews (2) Make Inquiry
    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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    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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    $750
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    1 / 7
    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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    $360
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    1 / 33
    4 of 5 stars (8) Very good
    Lee
    5 Bedrooms / 3 Bathrooms / Sleeps 11
    travelers have booked this property
    Overview Reviews (8) Make Inquiry
    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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    Location Information
    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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    5 of 5 stars (3) Excellent
    Alford
    1 Bedroom / 1 Bathroom / Sleeps 2
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    Amenities & Details
    • Hot Tub
    • Mountain Views
    • Satellite TV
    • Waterfront
    • Water Views
    • Wi-Fi
    • Air Conditioning
    • Housekeeping...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    The Smith Homestead in Alford Massachusetts has been homesteaded and farmed by our family for the past two centuries. Located on one of the nicest settings in the Berkshires, with 30 acres of fields and woods, and the crystal clear Alford Brook running through, we are central to all the cultural... View all property information
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    Alford, Massachusetts 01266
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    1 / 8
    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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    1 / 5
    West Stockbridge
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Inquiry
    Amenities & Details
    • Central Heating
    • Horse Riding Nearby
    • Watersports Nearby
    • Refrigerator
    • Wi-Fi
    • Patio
    • There Are Tennis...
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Architect-designed, one bedroom studio cottage in peaceful setting on quiet road with a 5 acre view! What more could you ask! Perfect haven for artist or writer or anyone wanting to get away! Only 15 minutes to Tanglewood or Kripalu This little gem has just been renovated, with built in couches,... View all property information
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    Location Information
    West Stockbridge, Berkshires 12029
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    $225
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    1 / 16
    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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    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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    $450
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    1 / 17
    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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    $200
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    5 of 5 stars (1) Excellent
    Lee
    1 Bedroom / 1 Bathroom / Sleeps 2
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    Amenities & Details
    • Hot Tub
    • Garage
    • Mountain Views
    • Internet Access
    • Air Conditioning
    • Fireplace
    • Stereo System
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    The Writer's Room is at the top of the stairs on the right. This handsome room is made completely of wood. Ceilings are higher and there's a sitting area in the big dormer. dormer faces east and get the morning sun! The floors are wide plank cherry milled from the property. the walls are pine.... View all property information
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    Location Information
    Lee, Berkshires 01238
    5 of 5 stars Reviewed June 17, 2014
    We have taken the Writer's Room each Summer for about three years now. We find the Lodge to be authentic New England... our natural wood room to the rest of the house. It is...
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    4 of 5 stars (1) Very good
    Lenox
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    traveler have booked this property
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    Amenities & Details
    • Playground
    • Stereo System
    • Mountain Views
    • DVD Player
    • TV
    • Internet Access
    • Deck
    • Central Heating
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Charming, spacious and comfortable 1860's farmhouse adjacent to wildlife sanctuary. Cozy country decor with original wide plank floors, lovely views and outdoor dining or lounging on porch or deck. Walking distance to hiking trails in Pleasant Valley Wildlife Preserve or Kennedy Park. Quiet and... View all property information
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    Lenox, Berkshires 01240
    4 of 5 stars Reviewed July 8, 2015
    Lovely farmhouse, convenient to Tanglewood and shops in Lenox as well as other nearby towns and sights. We were a family of 7, including a 2 year old, and the swing set in the...
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    Great Barrington
    5 Bedrooms / 3 Bathrooms / Sleeps 10
    traveler have booked this property
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    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
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    $400
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    1 / 24
    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
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    $675
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    1 / 22
    Great Barrington
    4 Bedrooms / 6 Bathrooms / Sleeps 12
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    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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    $165
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    East Chatham, NY
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    Amenities & Details
    • Wi-Fi
    • Horse Riding Nearby
    • Watersports Nearby
    • Mountain Views
    • DVD Player
    • Air Conditioning
    • There Are Tennis...
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Our cottage has been lovingly maintained and is in pristine condition. It is also very well laid out. You will enter through a generous foyer with closet and antique breakfront, and pass the media room (optional 3rd bedroom) with a divided light glass wall separating it from the family room. The... View all property information
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    Location Information
    East Chatham, New York 12060
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    $350
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    1 / 11
    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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    $150
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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 (5) Excellent
    West Stockbridge
    3 Bedrooms / 2 Bathrooms / Sleeps 7
    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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    $225
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    3.5 of 5 stars (3) 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
    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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    $500
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    1 / 25
    Great Barrington
    3 Bedrooms / 8 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Ping Pong Table
    • Game Room
    • Satellite TV
    • Central Heating
    • DVD Player
    • Wi-Fi
    • Hot Tub
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • x
    About this property
    SummerStone is an elegant country home beside a state forest the NYT once referred to as 'the best kept secret in the Berkshires'. Enjoy red oak floors, tumbled marble showers, cozy fireplaces and soaring ceilings. Go kayaking, biking, swimming or hiking then relax on the 600 sq. ft. porch. Ping... View all property information
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    Location Information
    Great Barrington, Berkshires 01258
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    $4,500
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    1 / 25
    Great Barrington
    6 Bedrooms / 6 Bathrooms / Sleeps 12
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    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
    $250
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    Great Barrington
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    traveler have booked this property
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    Amenities & Details
    • Stereo System
    • Satellite TV
    • Washer
    • Mountain Views
    • Deck
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • ?
    About this property
    Surrounded by one of the most beautiful gardens in the Berkshires, Maya's Garden House is an outstanding example of an 18th century barn converted into a modern, comfortable, semi-secluded home. Located less than a mile from Great Barrington, it is close to everything the Berkshires are famous for;... View all property information
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    Location Information
    Great Barrington, Berkshires 01230
    From
    $175
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    South Lee
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    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
    Two Bedroom two bathroom condo located on beautiful resort in the Berkshires. Oak and Spruce Resort located 15 minutes to Tanglewood is the summer home in the Berkshires of the Boston Symphony Orchestra. Condominium sleeps 6 with an eat in kitchen and living area. Recreational activities, ample... View all property information
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    Location Information
    South Lee, Berkshires 01260
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    $199
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    1 / 6
    East Chatham, NY
    5 Bedrooms / 3 Bathrooms / Sleeps 15
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    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    This rustic very private property, built in 2011 has sleeping accommodations for up to 15 people in the house. The cedar wood sauna and the grecian inground pool, as well as exquisite main cathedral hall makes the experience one of a kind. We have the following rooms 2 Bedrooms with queen size... View all property information
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    Location Information
    East Chatham, New York 12060
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    $175
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    1 / 2
    Lee
    1 Bedroom / 1 Bathroom / Sleeps 2
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    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
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    $1,700
    / Week
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    1 / 10
    4 of 5 stars (1) Very good
    Great Barrington
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Refrigerator
    • Porch
    • Deck
    • DVD Player
    • Washer
    • TV
    • Dryer
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Our home is located in Great Barrington, given the title of the #1 Best Small Town in America by Smithsonian Magazine. There are many great restaurants, shopping, the Mahaiwe theater, a cineplex, golf, natural foods Co-op, a State Forest, yoga studio, and more. There are about twelve (12!) hiking... View all property information
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    Location Information
    Great Barrington, Berkshires 01230
    4 of 5 stars Reviewed February 2, 2015
    My cousin and I thoroughly enjoyed our stay. The house was cozy and very convenient for our needs. Having a laundry room just off the kitchen was great when we came back from the...
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    $465
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    5 of 5 stars (3) Excellent
    Great Barrington
    4 Bedrooms / 3 Bathrooms / Sleeps 12
    traveler have booked this property
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    Amenities & Details
    • Game Room
    • Stereo System
    • Boat Available
    • DVD Player
    • Mountain Views
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    This sparkling, newly renovated cottage is for available vacation rental. A stunning sunrise & gorgeous view of the Berkshire Mountains. Conveniently located near many attractions. The house has been renovated by a contemporary designer. It has an open floor plan, making each room flow into... View all property information
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    Location Information
    Great Barrington, Berkshires 01230
    From
    $500
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    1 / 23
    5 of 5 stars (1) Excellent
    Stockbridge
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Water Views
    • Internet Access
    • Air Conditioning
    • Hot Tub
    • Mountain Views
    • Waterfront
    • Satellite TV
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    A home for the family: SKIING, SNOWSHOEING, AND SLEDDING. Fall and Winter availability. Behind the house, on the property is a HUGE hill that is great for sledding. 12 mins to Butternut. 25 mins to Jiminy. Across the road is a park that is great fun to hike, snowshoe, CC ski, and explore. A... View all property information
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    Location Information
    Stockbridge, Berkshires 01260
    From
    $100
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    1 / 9
    Canaan, NY
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Inquiry
    Amenities & Details
    • Grill
    • Boat Available
    • Wi-Fi
    • Air Conditioning
    • Refrigerator
    • Deck
    • Watersports Nearby
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    A cute cabin in the woods with easy access to a lake a short 500 ft walk down a dirt road. Swimming is available at a private member beach by either canoe or a sort drive to the other end of the the Lake. Convenient to the Berkshires. Tanglewood is a 15 min drive and Jacob's Pillow and Saratoga... View all property information
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    Location Information
    Canaan, New York 12029
    From
    $100
    / Night
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    1 / 8
    5 of 5 stars (1) Excellent
    Pittsfield
    1 Bedroom / 1 Bathroom / Sleeps 5
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Satellite TV
    • Shared Indoor Pool
    • Air Conditioning
    • DVD Player
    • Hot Tub
    • Internet Access
    • Stereo System
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    A Fully-Furnished Extended Stay property in the Berkshires. Located across the street from the Colonial Theatre and within minutes of most Berkshire County attractions. Each spacious, efficiency (condo-style) single bedroom apartment includes living room, kitchen with full size appliances,... View all property information
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    Location Information
    Pittsfield, Berkshires 01201
    5 of 5 stars Reviewed July 3, 2013
    WOW, this place was very nice! What you get is a place with a five minute walk from downtown, well kept buidlings and grounds, excellent floor plans, new furniture, modern...
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    $200
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    1 / 18
    Austerlitz, NY
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
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    Amenities & Details
    • TV
    • Washer
    • Mountain Views
    • DVD Player
    • Deck
    • Stereo System
    • Fireplace
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This 3 Bedroom 2.5 bathroom recently constructed home sits on 40 wooded, secluded acres in Austerlitz, Columbia County, just 4 miles from the Massachusetts border. It offers stunning views of the Catskills, peace and quite and plenty of nature to watch from the back porch. Chatham, NY is 15 minutes... View all property information
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    Location Information
    Austerlitz, New York 12017
    From
    $300
    / Night
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    1 / 12
    New Lebanon, NY
    5 Bedrooms / 5 Bathrooms / Sleeps 5
    Overview Make Inquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    This home sits on 10 private acres in the beautiful Berkshire mountains. Greeted by friendly wood carved bears, the entire estate consists of a 3 BR main house with 3.5 baths, two bedroom pool house with 1 bath, and 1 bedroom garage apartment with 1 bath. All units are available but this listings... View all property information
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    Location Information
    New Lebanon, New York 12125
    From
    $375
    / Night
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    1 / 5
    Lee
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Sauna
    • Air Conditioning
    • Hot Tub
    • Internet Access
    • Mountain Views
    • Shared Indoor Pool
    • Shared Tennis Court
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    I have a corner unit first floor 2-bed resort presidential suite in beautiful Berkshires! Just 2 hours drive down the Mass Pike from Boston. It's July 4th week and James Taylor will be playing at Tanglewood. This is one of the most sought after concerts every year and you wouldn't want to miss it!... View all property information
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    Location Information
    Lee, Berkshires 01238
    From
    $200
    / Night
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    1 / 14
    Austerlitz, NY
    1 Bedroom / 1 Bathroom / Sleeps 5
    Overview Make Inquiry
    Amenities & Details
    • Grill
    • Linens Provided
    • TV
    • Wi-Fi
    • Air Conditioning
    • Refrigerator
    • Stove
    • Fireplace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Newly built cabin in the woods. The cabin is perfect for a small family or couple. It is a perfect location for wanting to be close to the Berkshires, Hudson NY, and Copake Lake. Tons of hiking trails and swimming lakes for the summer and minutes from Butternut and Catamount ski resorts in the... View all property information
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    Location Information
    Austerlitz, New York 12017
    From
    $250
    / Night
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    1 / 11
    4 of 5 stars (2) Very good
    Lee
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • Mountain Views
    • Internet Access
    • Dryer
    • Satellite TV
    • Washer
    • DVD Player
    • Stereo System
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Experience a little of old New England. Our vacation rental is a charming historic family farmhouse apartment with lots of room and comfort,2100Sq.ft., situated on 22 acres. Built in 1782, our farm was famous for breeding Plymouth Barred Rock chickens. In the 1800's, one of these barred rock... View all property information
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    Location Information
    Lee, Berkshires 01238
    4 of 5 stars Reviewed June 18, 2013
    This property was a great home base for our brief visit to the Berkshires. Plenty of space and well equipped. We especially enjoyed the beautiful property, whether sitting on the...
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