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Search results; Over 1,000 homes in Great Barrington

Top guest favourite
Cottage in Great Barrington
Cottage on Scenic Road
1 bedroom, 1 bed, 1 private bathroom
13–18 Sept
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4.91 out of 5 average rating, 281 reviews
Top guest favourite
Cottage in Great Barrington
Carriage house with Chef's Kitchen, close to town
2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
4.93 out of 5 average rating, 158 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
Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
3 bedrooms, 4 beds, 1 bathroom
13–18 Sept
4.95 out of 5 average rating, 175 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
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms, 4 beds, 2 bathrooms
10–15 Sept
4.9 out of 5 average rating, 10 reviews
Guest favourite
Home in Great Barrington
Lovely house in the Berkshires
3 bedrooms, 4 beds, 1.5 bathrooms
11–16 Sept
4.87 out of 5 average rating, 31 reviews
Guest favourite
Holiday home in Great Barrington
Home in Great Barrington. Steps from downtown!
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
4.94 out of 5 average rating, 294 reviews
Top guest favourite
Home in Great Barrington
Prime location for the best of the Berkshires
2 bedrooms, 2 queen beds, 1 bathroom
11–16 Sept
4.97 out of 5 average rating, 141 reviews
Top guest favourite
Home in Great Barrington
Modern Victorian- Walk to Town
4 bedrooms, 7 beds, 2.5 bathrooms
14–19 Sept
4.97 out of 5 average rating, 142 reviews
Guest favourite
Treehouse in New Marlborough
Berkshire Treehouse Retreat
3 bedrooms, 4 beds, WC
12–17 Sept
4.9 out of 5 average rating, 178 reviews
Top guest favourite
Flat in Great Barrington
Walk Everywhere! | Relax in Easy Elegance!
2 bedrooms, 3 beds, 2 bathrooms
18–23 Sept
5.0 out of 5 average rating, 149 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
Flat in Great Barrington
The River’s Whisper
2 bedrooms, 2 queen beds, 1 bathroom
16–21 Sept
4.98 out of 5 average rating, 48 reviews
Guest favourite
Chalet in Great Barrington
Berkshire "Zen" Cottage
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.94 out of 5 average rating, 88 reviews
Guest favourite
Flat in Great Barrington
Berkshire Retreat|King Bed|Wi-Fi|2m Ski Resort
1 king bed, 1 bathroom
20–25 Sept
4.89 out of 5 average rating, 187 reviews
Top guest favourite
Home in Great Barrington
Fall Foliage @ The Barrington House: GB
5 bedrooms, 6 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Cottage in Monterey
Beaver Lodge
3 bedrooms, 3 queen beds, 1.5 bathrooms
10–15 Sept
5.0 out of 5 average rating, 83 reviews
Superhost
Home in Great Barrington
Pristine 3 Bedroom, Walk-to Gt Barrington Center!
3 bedrooms, 4 beds, 1.5 bathrooms
10–15 Sept
4.88 out of 5 average rating, 24 reviews