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Holiday Homes in Great Barrington

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    Travellers to Great Barrington are booking May 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 / 18
    (24)Excellent
    Great Barrington
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Lakefront Berkshires Ski/Summer House, Great Views1 / 17
    (4)Very good
    Great Barrington
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Gem of the Berkshires, walk to downtown & lake.1 / 30
    (4)Excellent
    Great Barrington
    5 Bedrooms, 4 Bathrooms, Sleeps 12 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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    Amenities & Details
    • Porch
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • Mountain Views
    • DVD Player
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 September 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...
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    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,...
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    01230, Great Barrington, Berkshires
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Great Barrington
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Secure Parking
    • Wi-Fi
    • Private Garden
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In 2016 Smithsonian Magazine deemed Great Barrington, 'The Best Small Town in America.' Manor Lane is a private French Country Estate located only 5 minutes from the heart of the Berkshires. Situated 10 minutes to both Butternut and Catamount ski mountains and 25 minutes to Tanglewood. Manor Lane...
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    01230, Great Barrington, Berkshires
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
    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
    • Cable/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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    01230, Great Barrington, Berkshires
    Holiday Rental House - 9 Bedrooms, 8 Bathrooms, Sleeps 16
    Cozy and clean in Gt Barrington- available for October1 / 14
    (1)Very good
    Great Barrington
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Parking
    • Private Garden
    • Porch
    • Outdoor Dining Area
    • Washer
    • Wi-Fi
    • DVD Player
    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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    01230, Great Barrington, Berkshires
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Great Barrington
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Balcony
    • Washer
    • Waterfront
    • Cable/satellite TV
    • Hot Tub
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Impeccable home and location. Recently upgraded, modern home provides a luxurious experience. Nestled above a lake on a quiet dirt road this home provides privacy and peace while only being minutes from downtown Great Barrington. Kitchen is equipped with stainless appliances and granite counter...
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    01230, Great Barrington, Berkshires
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Great Barrington
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Grill
    • Air Conditioning
    • Skiing: Property Is In A Ski Resort
    • Patio
    • Parking
    • Washer
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    When you pull into our long private driveway surrounded by nature, Our lovely cottage style home greets you with a rustic yet modern grey board and batten exterior and the sense of “coming home.” You then enter the home from a small wood deck that leads into the open concept kitchen/dining area....
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    01230, Great Barrington, Berkshires
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Great Barrington
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This updated home has a luxurious feel! Close proximity to downtown Great Barrington is convenient and allows for easy access to the world's cultural epicenter. Located on a dirt road in a gentle neighborhood. About 1/2 mile from Lake Mansfield. Dehon road cuts over to the lake! The upgraded...
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    Location Information
    01230, Great Barrington, Berkshires
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Great Barrington
    7 Bedrooms, 8 Bathrooms, Sleeps 15 Quick View
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    Amenities & Details
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming former tavern and stage coach inn makes the perfect 4 season getaway for large group gatherings, family reunions, weddings or any occasion. Enjoy everything the Berkshires has to offer from the shops and restaurants in Great Barrington, skiing at Butternut Ski resort, and music and...
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    01230, Great Barrington, Berkshires
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 15
    Great Barrington
    6 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Air Conditioning
    • Mountain Views
    • Cable/satellite TV
    • Grill
    • Washer
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The best vacation home in the Berkshires (ALL SEASONS): 9 private acres (far away from roads and neighbors), 6,800 ft² of living space, 6 bedrooms, sleeps 10 very comfortably. Ideal for 1, 2 or 3 families or those wonderful family reunions. There is a very large heated swimming pool. The pool is...
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    Location Information
    01230, Great Barrington, Berkshires
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 10
    The following rentals are within 10 kilometres of Great Barrington.
    RiverSong Suite In The Berkshires1 / 52
    (15)Excellent
    North Egremont
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Patio
    • Air Conditioning
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 June 2019
    We were visiting friends in Great Barrington and found this wonderful place.It is right on a small river with lovely grounds. The hosts were very helpful.
    Reviewed 19 August 2018
    We eagerly anticipated our stay at RiverSong. Based on the plethora of five-star reviews we expected near-perfection. While we loved the atmosphere, fabulous comfortable bed...
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    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,...
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    01230, North Egremont, Berkshires
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    North Egremont
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Cable/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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    01230, North Egremont, Berkshires
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    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
    • Cable/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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    01266, Alford, Berkshires
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    The Smith Farm Homestead1 / 12
    (6)Excellent
    Alford
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Hot Tub
    • Mountain Views
    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 October 2018
    This was a perfect place for a bit of R & R. Friendly owners and luxurious room that was clean and comfortable. The home has a historical atmosphere in a beautiful country...
    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!
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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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    01266, Alford, Berkshires
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    NEW! Lakefront Berkshires House w/Deck, Dock +Boat1 / 26
    (1)Average
    Housatonic
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Washer
    • Central Heating
    • Skiing: Property Is In A Ski Resort
    • Cable/satellite TV
    • Waterfront
    • Wi-Fi
    • Mountain Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 September 2019
    My family liked the decor, had space to sleep with all our kids, and was close to great small towns in the Berkshires. The house was clean, had plenty of hot water and laundry...
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    About this property
    Leave your busy schedule behind for a life of leisure at this vacation rental hideaway. This 4-bedroom, 2-bath home is complete with woodsy-style decor, contemporary furnishings, and space for 10. It's truly a sportsman's paradise - tucked away in the woods on Round Pond, where you can hike, fish,...
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    Location Information
    01230, Housatonic, Berkshires
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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