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Search results; Over 1,000 homes in Great Barrington

Guest favourite
Cottage in Great Barrington
The Cottage at The Barrington House
1 bedroom, 1 bed, 1 private bathroom
22–27 Aug
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4.94 out of 5 average rating, 217 reviews
Top guest favourite
Flat in Great Barrington
King Bed | Patio | 2m to Ski Resort
1 king bed, 1 bathroom
23–28 Aug
4.91 out of 5 average rating, 175 reviews
Guest favourite
Flat in Great Barrington
King Bed|ADA ROOM|2m Ski Resort
1 king bed, 1 bathroom
22–27 Aug
4.9 out of 5 average rating, 72 reviews
Guest favourite
Room in Great Barrington
Quiet refuge in Great Barrington
1 queen bed, 1 bathroom
14–19 Sept
4.93 out of 5 average rating, 237 reviews
Guest favourite
Cottage in Great Barrington
Cottage on Scenic Road
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
4.91 out of 5 average rating, 276 reviews
Top guest favourite
Room in North Chatham
Charming Eyebrow Colonial North Chatham, NY
1 king bed, 1 bathroom
30 Aug – 4 Sept
4.97 out of 5 average rating, 617 reviews
Top guest favourite
Loft in Great Barrington
The Old Red Barn
1 bedroom, 1 queen bed, 1 bathroom
8–13 Sept
4.99 out of 5 average rating, 366 reviews
Top guest favourite
Room in Great Barrington
Large, light bedroom on The Hill (Eco Airbnb)
1 double bed, 1 bathroom
27 Aug – 1 Sept
4.97 out of 5 average rating, 31 reviews
Top guest favourite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
2 bedrooms, 2 queen beds, 1 bathroom
27 Aug – 1 Sept
4.99 out of 5 average rating, 69 reviews
Top guest favourite
Home in Great Barrington
Seekonk Hill
2 bedrooms, 2 beds, 2 bathrooms
26–31 Oct
4.98 out of 5 average rating, 44 reviews
Guest favourite
Room in Town of Ancram
The Doodletown
1 double bed, 1 bathroom
17–22 Aug
4.96 out of 5 average rating, 214 reviews
Top guest favourite
Guest house in Stockbridge
Modern studio with views of the treetops
2 beds, 1 bathroom
23–28 Aug
4.96 out of 5 average rating, 309 reviews
Superhost
Cabin in Monterey
Secluded cabin with babbling brook
3 bedrooms, 3 beds, 1 bathroom
25–30 Oct
4.87 out of 5 average rating, 256 reviews
Superhost
Barn in Canaan
The Cobble Barn | Fireplace • A/C • Screened Porch
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
New place to stay
Top guest favourite
Bungalow in Egremont
3-bedroom Berkshire bungalow on 2.5 peaceful acres
3 bedrooms, 5 beds, 2 bathrooms
13–18 Sept
4.99 out of 5 average rating, 137 reviews
Guest favourite
Home in Sheffield
Bull Hill Bungalow
3 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
4.98 out of 5 average rating, 54 reviews
Guest favourite
Guest house in Great Barrington
Berkshires Guest Barn
2 bedrooms, 5 beds, 1 bathroom
16–21 Aug
4.95 out of 5 average rating, 37 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
Top guest favourite
Guest suite in Great Barrington
The Serendipity Spot
1 bedroom, 1 bed, 1 bathroom
16–21 Aug
4.95 out of 5 average rating, 55 reviews