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Search results; Over 1,000 homes in Great Barrington

Top guest favourite
Cottage in Great Barrington
Carriage house with Chef's Kitchen, close to town
2 bedrooms, 3 beds, 1.5 private bathrooms
9–14 Nov
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4.93 out of 5 average rating, 157 reviews
Guest favourite
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
4.9 out of 5 average rating, 10 reviews
Top guest favourite
Home in Great Barrington
Sauna + Hot Tub Escape | Private & Pet Friendly
3 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 56 reviews
Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
3 bedrooms, 4 beds, 1 bathroom
8–13 Sept
4.95 out of 5 average rating, 175 reviews
Guest favourite
Flat in Great Barrington
King Bed|Wi-Fi|2m Ski Resort|Studio
1 king bed, 1 bathroom
13–18 Sept
4.84 out of 5 average rating, 116 reviews
Top guest favourite
Home in Great Barrington
A Berkshires Abode - Minutes to Ski & Downtown GB!
3 bedrooms, 4 beds, 3 bathrooms
8–13 Sept
4.97 out of 5 average rating, 31 reviews
Top guest favourite
Cottage in Great Barrington
Artist Cottage
1 bedroom, 1 queen bed, 2 bathrooms
1–6 Dec
4.93 out of 5 average rating, 353 reviews
Guest favourite
Home in Great Barrington
Lovely house in the Berkshires
3 bedrooms, 4 beds, 1.5 bathrooms
9–14 Sept
4.87 out of 5 average rating, 31 reviews
Guest favourite
Cottage in Sheffield
Cheerful 3-bedroom cottage with woodstove.
3 bedrooms, 3 beds, 2.5 bathrooms
20–25 Sept
4.92 out of 5 average rating, 193 reviews
Home in Great Barrington
Riverside Retreat in the Berkshires
3 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.59 out of 5 average rating, 37 reviews
Top guest favourite
Home in Great Barrington
Stunning luxury home with pool
4 bedrooms, 4 beds, 4.5 bathrooms
9–14 Sept
4.99 out of 5 average rating, 94 reviews
Top guest favourite
Home in Great Barrington
The Yellow Victorian With Chefs Kitchen
3 bedrooms, 4 beds, 3.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 59 reviews
Top guest favourite
Guest house in Great Barrington
Trailside Cottage
1 bedroom, 3 beds, 1 bathroom
29 Oct – 3 Nov
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Great Barrington
Prime location for the best of the Berkshires
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Sept
4.97 out of 5 average rating, 140 reviews
Guest favourite
Home in Great Barrington
The Summerwood Hideout | Mins to Downtown! • Pool
4 bedrooms, 4 beds, 4 bathrooms
8–13 Sept
4.89 out of 5 average rating, 18 reviews
Guest favourite
Home in Great Barrington
Berkshire’s Best-hottub-fitness/gameroom
4 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
4.92 out of 5 average rating, 24 reviews
Top guest favourite
Home in Great Barrington
GB at your doorstep
3 bedrooms, 4 beds, 2 bathrooms
9–14 Sept
4.94 out of 5 average rating, 140 reviews
Guest favourite
Home in Great Barrington
Berkshires Retreat!
5 bedrooms, 9 beds, 2.5 bathrooms
10–15 Sept
4.95 out of 5 average rating, 40 reviews
Top guest favourite
Home in Great Barrington
Country Castle-Complete privacy-minutes from town
6 bedrooms, 8 beds, 3 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 66 reviews