Great Barrington Holiday Homes
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All 15 Rentals in Great Barrington
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Great Barrington
1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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Great Barrington
4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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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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Great Barrington, Berkshires 01230
Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
Great Barrington
5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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Amenities & Details
- Mountain Views
- Patio
- Grill
- Washer
- Cable/satellite TV
- Wi-Fi
- DVD Player
- Air Conditioning
Suitability
Pet friendly
Kid friendly
Smoking allowed
Reviewed 16 March 2018
This home is a wonderfully appointed home, conveniently located just outside of town. It was perfect for our multiple family ski getaway. The owner is thorough in helping...
About this property
This sparkling, newly renovated 3 floors house is for available vacation rental. A stunning sunrise & gorgeous view of the Berkshire Mountains. Conveniently located near many attractions, such as Tanglewood, Butternut ski, etc
The house has an open floor plan, making each room flow into another....
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Great Barrington, Berkshires 01230
Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
Great Barrington
4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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Amenities & Details
- Washer
- Cable/satellite TV
- Wi-Fi
- Mountain Views
- Grill
- DVD Player
- Waterfront
- Central Heating
Suitability
Pet friendly
Kid friendly
Smoking allowed
Reviewed 17 November 2017
The house was cozy. The lake was beautiful. The surrounding towns offer great restaurants. The host was very helpful.
Reviewed 17 November 2017
We rented this lovely home on the lake (or maybe it's a pond... Long Pond I think) last year and loved every minute of our visit. The house is well equipped and has all one...
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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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...
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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Great Barrington, Berkshires 01230
Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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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Great Barrington, Berkshires 01230
Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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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Great Barrington, Berkshires 01230
Holiday Rental House - 9 Bedrooms, 8 Bathrooms, Sleeps 16
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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.
The Space:
Quaint cottage with wood burning stove. Ideal base for enjoying...
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Great Barrington, Berkshires 01230
Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
The following rentals are within 10 kilometres of Great Barrington.
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Payment Protection
Amenities & Details
- Wi-Fi
- Grill
- Cable/satellite TV
- Waterfront
- DVD Player
- Patio
- Air Conditioning
- Mountain Views
Suitability
Pet friendly
Kid friendly
Smoking allowed
Reviewed 4 weeks ago
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...
Reviewed 3 November 2017
Riversong suite was wonderful, situated in a great location. Close to nearby restaurants and shops yet far from all the noise. Peaceful and quiet. A great place to renew...
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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North Egremont, Berkshires 01230
Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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North Egremont, Berkshires 01230
Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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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 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...
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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Alford, Berkshires 01266
Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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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...
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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Alford, Berkshires 01266
Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
North Egremont
5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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Amenities & Details
- Air Conditioning
- Patio
- Cable/satellite TV
- DVD Player
- Washer
- Private Outdoor Pool (Unheated)
- Skiing: Property Is In A Ski Resort
- Wi-Fi
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
Book a one-of-a-kind stay in this 5-bedroom, 4.5-bathroom vacation rental home in South Egremont. Built from the bones of a 15th-century British barn, this 4,000-square-foot home for 10 is one of the oldest structures in Massachusetts! Whether you were drawn to the Berkshires by the natural beauty...
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North Egremont, Berkshires 01258
Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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