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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
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4.93 out of 5 average rating, 342 reviews
Guest favourite
Flat in Great Barrington
King Bed, Wi-Fi, 2m Ski Resort
1 king bed
5–10 Jul
4.95 out of 5 average rating, 176 reviews
Top guest favourite
Home in Great Barrington
Private Home in The Berkshires (New Hot Tub!)
2 bedrooms, 2 queen beds
28 Jul – 2 Aug
4.99 out of 5 average rating, 124 reviews
Top guest favourite
Loft in Great Barrington
The Old Red Barn
1 bedroom, 1 queen bed
1–6 Sept
4.99 out of 5 average rating, 361 reviews
Superhost
Home in Monterey
Dog-Friendly Berkshires Retreat w/Fenced Yard
3 bedrooms, 3 beds
28 Jul – 2 Aug
New place to stay
Guest favourite
Home in Great Barrington
Lovely house in the Berkshires
3 bedrooms, 4 beds
7–12 Sept
4.95 out of 5 average rating, 22 reviews
Guest favourite
Tiny home in New Marlborough
Bedroom Forest View I Sauna I Fire-pit I Trails
2 bedrooms, 2 beds
28 Jul – 2 Aug
4.94 out of 5 average rating, 174 reviews
Top guest favourite
Cabin in Great Barrington
Modern Luxury Log Cabin
4 bedrooms, 6 beds
23–28 Aug
4.96 out of 5 average rating, 112 reviews
Top guest favourite
Home in Great Barrington
Prime location for the best of the Berkshires
2 bedrooms, 2 queen beds
9–14 Sept
4.97 out of 5 average rating, 133 reviews
Guest favourite
Room in Pittsfield
Cute Room with Bay Window in Downtown Victorian
2 beds
12–17 Jul
5.0 out of 5 average rating, 14 reviews
Guest favourite
Treehouse in New Marlborough
Berkshire Treehouse Retreat
3 bedrooms, 4 beds
12–17 Jul
4.9 out of 5 average rating, 157 reviews
Guest favourite
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms, 4 beds
23–28 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
3 bedrooms, 4 beds
12–17 Jul
4.96 out of 5 average rating, 165 reviews
Flat in Stockbridge
Quaint & cozy loft
1 bedroom, 1 queen bed
1–6 Jul
Top guest favourite
Flat in Great Barrington
King Bed|Wi-Fi|2m Ski Resort|Studio|Berkshires
1 king bed
6–11 Jul
4.93 out of 5 average rating, 161 reviews
Top guest favourite
Home in Sheffield
Family friendly house with fenced yard & fire pit
3 bedrooms, 3 beds
26–31 Jul
4.96 out of 5 average rating, 23 reviews
Guest favourite
Home in Sheffield
52-Acre Berkshires Farmhouse • Fire Pit + Trails
4 bedrooms, 9 beds
5–10 Jul
5.0 out of 5 average rating, 6 reviews
Guest favourite
Flat in Great Barrington
Kitchenette|King Bed|Couch
1 bedroom, 1 king bed
23–28 Aug
4.89 out of 5 average rating, 180 reviews
Guest favourite
Home in Sheffield
Water-View Home in the Berkshires
3 bedrooms, 4 beds
4–9 Jul
4.97 out of 5 average rating, 32 reviews