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Search results; Over 1,000 homes in Great Barrington

Top guest favourite
Cottage in Great Barrington
Artist Cottage
1 bedroom, 1 bed, 2 private bathrooms
7–12 Sept
,
4.93 out of 5 average rating, 342 reviews
Guest favourite
Flat in Great Barrington
King Bed, Wi-Fi, 2m Ski Resort
4.95 out of 5 average rating, 176 reviews, 1 bed, 1 bathroom
5–10 Jul
Superhost
Home in Monterey
Dog-Friendly Berkshires Retreat w/Fenced Yard
New place to stay, 3 bedrooms, 3 beds, 2.5 bathrooms
28 Jul – 2 Aug
Top guest favourite
Home in Sheffield
Family friendly house with fenced yard & fire pit
4.96 out of 5 average rating, 23 reviews, 3 bedrooms, 3 beds, 2 bathrooms
11–16 Jul
Top guest favourite
Home in Great Barrington
Prime location for the best of the Berkshires
4.97 out of 5 average rating, 132 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Sept
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
Guest favourite
Tiny home in New Marlborough
Bedroom Forest View I Sauna I Fire-pit I Trails
4.94 out of 5 average rating, 174 reviews, 2 bedrooms, 2 beds, 1 bathroom
28 Jul – 2 Aug
Guest favourite
Flat in Great Barrington
Kitchenette|King Bed|Couch
4.89 out of 5 average rating, 180 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Aug
Top guest favourite
Flat in Great Barrington
Walk Everywhere! | Relax in Easy Elegance!
5.0 out of 5 average rating, 142 reviews, 2 bedrooms, 3 beds, 2 bathrooms
29 Aug – 3 Sept
Top guest favourite
Home in Lee
Berkshire 4 season home
4.98 out of 5 average rating, 248 reviews, 3 bedrooms, 3 beds, 2 bathrooms
25–30 Oct
Flat in Stockbridge
Quaint & cozy loft
1 bedroom, 1 bed, 1 bathroom
1–6 Jul
Top guest favourite
Cabin in Great Barrington
Modern Luxury Log Cabin
4.96 out of 5 average rating, 112 reviews, 4 bedrooms, 6 beds, 3 bathrooms
19–24 Jul
Top guest favourite
Home in Great Barrington
Walt's Townhouse - Berkshire living at its best
5.0 out of 5 average rating, 83 reviews, 3 bedrooms, 3 beds, 2 bathrooms
13–18 Oct
Guest favourite
Guest suite in Great Barrington
The Serendipity Spot
4.94 out of 5 average rating, 53 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Jul
Guest favourite
Home in Sheffield
Water-View Home in the Berkshires
4.97 out of 5 average rating, 32 reviews, 3 bedrooms, 4 beds, 2 bathrooms
4–9 Jul
Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
4.96 out of 5 average rating, 165 reviews, 3 bedrooms, 4 beds, 1 bathroom
12–17 Jul
Top guest favourite
Flat in Great Barrington
King Bed|Wi-Fi|2m Ski Resort|Studio|Berkshires
4.93 out of 5 average rating, 161 reviews, 1 bed, 1 bathroom
6–11 Jul
Guest favourite
Home in Sheffield
52-Acre Berkshires Farmhouse • Fire Pit + Trails
5.0 out of 5 average rating, 6 reviews, 4 bedrooms, 9 beds, 2.5 bathrooms
5–10 Jul
Top guest favourite
Home in Great Barrington
Country Castle-Complete privacy-minutes from town
4.98 out of 5 average rating, 61 reviews, 6 bedrooms, 8 beds, 3 bathrooms
4–9 Jul