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Great Barrington Holiday Homes

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    Travellers to Great Barrington are booking August dates now. Secure your holiday rental today, and have the perfect trip.
    All 17 Rentals in Great Barrington
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    Berkshires: Romantic Cottage with spectacular view1 / 13
    (21)Excellent
    Great Barrington
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Shaker Hill1 / 27
    (2)Average
    Great Barrington
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Gem of the Berkshires, walk to downtown & lake.1 / 30
    (3)Excellent
    Great Barrington
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Great Barrington
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Wi-Fi
    • Parking
    • Mountain Views
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One bedroom, one bathroom cottage on beautiful country road. Private garden and screened-in porch. Two miles to shops and restaurants of downtown Great Barrington. Enjoy nearby skiing, cycling, fishing, hiking and golf.<BR><BR>The Space:<BR><BR>Quaint cottage with wood burning stove. Ideal base for...
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    Great Barrington, Berkshires 01230
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Lakefront Berkshires Ski/Summer House, Great Views1 / 12
    (2)Average
    Great Barrington
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Washer
    • Satellite TV
    • Internet Access
    • Mountain Views
    • Grill
    • DVD Player
    • Waterfront
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 June 2017
    Ray was very quick to respond to all our rental questions. We had a wonderful weekend at this home. It was very clean and welcoming to our party of 6 . The kitchen was fully...
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    About this property
    Located in a wooded area overlooking a pristine lake, this woodsy style contemporary is a sportsman's paradise. It's a short drive to skiing (Jiminy Peak, Butternut, Catamount) and cultural attractions, (Tanglewood, National Music Center, Aston Magna, etc.) or you can fish, swim, boat, hike, or...
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    Great Barrington, Berkshires 01236
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Great Barrington
    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Parking
    • Grill
    • Outdoor Dining Area
    • Air Conditioning
    • Washer
    • Internet Access
    • Shared Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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,...
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    Great Barrington, Berkshires 01236
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 12
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    Great Barrington
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Balcony
    • Mountain Views
    • Washer
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Restored 1940's log cabin, amazing undisturbed 30 mile, 180 degree views. Hilltop location, walking distance to the village of South Egremont, ideal for hiking, Appalachian trail nearby, minutes to all major Berkshire attractions, very private & quiet, abundant wildlife, deer, fox, hawks, turkey....
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    Great Barrington, Berkshires
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Cozy and clean in Gt Barrington- 1 week in summer!1 / 10
    (1)Very good
    Great Barrington
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Outdoor Dining Area
    • DVD Player
    • Parking
    • Porch
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Great Barrington, Berkshires 01230
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Great Barrington
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Internet Access
    • Mountain Views
    • Satellite TV
    • Patio
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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 6,700 sf of living space (3 floors) with plenty of places to be together or to be alone (as one so chooses)....
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    Great Barrington, Berkshires 01230
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    Great Barrington
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Patio
    • DVD Player
    • Central Heating
    • Terrace
    • Balcony
    • Housekeeping Included
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Secluded high on a mountainside and surrounded by thousands of acres of state park and conservation land, The Pod is a rustic early 1970's timber and glass octagon set on a concrete pedestal. Decks on four sides with forest or distant mountain views. One stream runs within 15 feet of the master...
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    Location Information
    Great Barrington, Berkshires 01230
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Great Barrington
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Central Heating
    • Internet Access
    • Grill
    • Satellite TV
    • Waterfront
    • DVD Player
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience the splendor of the Berkshires from this 3-bedroom, 2-bathroom vacation rental house which sleeps 8 in Great Barrington. Situated on a 3-acre lot overlooking the Housatonic River, this home provides an idyllic setting for your retreat. Not only can you relax in the tranquility of your...
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    Great Barrington, Berkshires 01230
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Great Barrington
    9 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Grill
    • Patio
    • Wi-Fi
    • Washer
    • Hot Tub
    • Air Conditioning
    • Satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is by far one of the nicest homes that you will come across in the area (or this site for that matter!). The estate comes complete with 7 bedroom, 7 bathroom main house, a guest house with 2 bedrooms and one bath, several fire places, a pool table, ping pong table, pool, jacuzzi, several TV's...
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    Location Information
    Great Barrington, Berkshires 01230
    Holiday Rental House - 9 Bedrooms, 8 Bathrooms, Sleeps 16
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    The following rentals are within 10 kilometres of Great Barrington.
    RiverSong Suite In The Berkshires1 / 52
    (10)Excellent
    North Egremont
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travellers have booked this property
    Certificate of Excellence
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    Amenities & Details
    • Wi-Fi
    • Grill
    • Satellite TV
    • Waterfront
    • DVD Player
    • Patio
    • Air Conditioning
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 March 2017
    I was very skeptical about staying somewhere other than a "chain hotel or resort". That is until I met Barbara and Phil. They were a very gracious, humble and warm...
    Reviewed 17 November 2016
    River Song is a wonderfully private and relaxing place to hang your hat before heading out to visit Great Barrington and all the beauty that the Berkshires offers in any season...
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    About this property
    Located in the Berkshire mountains on more than 5 acres <BR>surrounded by 29 acres of conservation land. Featuring<BR>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,...
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    Location Information
    North Egremont, Berkshires 01230
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    The Smith Farm Homestead1 / 12
    (5)Excellent
    Alford
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Hot Tub
    • Mountain Views
    • Satellite TV
    • Waterfront
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 February 2017
    Cozy and pretty room and bathroom suite that I shared with my teenaged daughter. Susan is very welcoming and friendly. We loved our stay here and would return!
    Reviewed 17 October 2016
    This is a terrific B&B. Lovely, spacious, comfortable room looking out over rolling pastures and forest. Fabulous breakfasts delivered to your room in a basket: fresh baked...
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    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...
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    Location Information
    Alford, Berkshires 01266
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Lake House in the Berkshires1 / 19
    (1)Excellent
    North Egremont
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Patio
    • Grill
    • Balcony
    • Parking
    • DVD Player
    • Air Conditioning
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 October 2015
    It's my first time booking through flipkey. Zoe, the hostess, helped me a lot during the process. She is warm, kind, and patient. Her email was in details and we checked in...
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    About this property
    Enjoy beautiful Prospect Lake while staying at our comfortable home. Full kitchen with almost anything you can think of. Farm table seats 8 and is perfect for family meal. Cozy living spaces with enough seating for all to gather. Sunny bright deck in private rear yard . Covered porch is perfect...
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    Location Information
    North Egremont, Berkshires 01230
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Berkshire Getaway at 'Tofu'S Retreat'1 / 22
    (1)Excellent
    Alford
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 May 2017
    The screen door to the patio stuck a little. That's it. Period. Otherwise, this place was perfect! Three adults (two seniors), two children, and one dog spent a spectacular week...
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    About this property
    Wonderful Alford upscale family home with in ground heated pool; art barn, acreage; lush view & privacy. Private tranquil getaway vacation home.Delightful tri-level saltbox which has been completely, thoughtfully & tastefully renovated with every comfort in mind. Main floor: Enters into a breath...
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    Location Information
    Alford, Berkshires 01266
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    North Egremont
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Satellite TV
    • Mountain Views
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our nearly new home we call RiverSong is on 5.5 acres surrounded by almost 30 more conservation land of meadow and farmland. The pristine Green River is right in our back yard with a wonderful swimming hole. Our Penthouse room is on the upper level of our home. A Bright and spacious king size...
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    Location Information
    North Egremont, Berkshires 01230
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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