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Search results; Over 1,000 homes in Great Barrington

Guest favourite
Home in Great Barrington
Waterfront Modern Lake Mansfield Retreat
3 bedrooms, 3 beds, 2.5 private baths
Sep 14–19
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4.97 out of 5 average rating, 76 reviews
Guest favourite
Treehouse in New Marlborough
Berkshire Treehouse Retreat
3 bedrooms, 4 beds, Half-bath
Aug 23–28
4.91 out of 5 average rating, 170 reviews
Guest favourite
Room in Great Barrington
Quiet refuge in Great Barrington
1 queen bed, 1 bath
Sep 14–19
4.93 out of 5 average rating, 236 reviews
Top guest favourite
Apartment in Great Barrington
King Bed | Patio | 2m to Ski Resort
1 king bed, 1 bath
Aug 23–28
4.91 out of 5 average rating, 174 reviews
Top guest favourite
Home in Great Barrington
Prime location for the best of the Berkshires
2 bedrooms, 2 queen beds, 1 bath
Sep 9–14
4.97 out of 5 average rating, 137 reviews
Guest favourite
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms, 4 beds, 2 baths
Aug 23–28
4.89 out of 5 average rating, 9 reviews
Top guest favourite
Cottage in Monterey
Beaver Lodge
3 bedrooms, 3 queen beds, 1.5 baths
Sep 10–15
5.0 out of 5 average rating, 83 reviews
Guest favourite
Apartment in Great Barrington
King Bed |Wi-Fi| 2m to Ski Resort
1 king bed, 1 bath
Aug 30–Sep 4
4.92 out of 5 average rating, 213 reviews
Guest favourite
Guesthouse in Great Barrington
Berkshires Guest Barn
2 bedrooms, 5 beds, 1 bath
Aug 16–21
4.95 out of 5 average rating, 37 reviews
Guest favourite
Place to stay in Stockbridge
Cozy room w/private bath–near Tanglewood/Kripalu
1 bedroom, 1 bed, 1 bath
Aug 23–28
4.85 out of 5 average rating, 161 reviews
Guest favourite
Guesthouse in Great Barrington
Sweet Victorian in Housatonic
3 bedrooms, 4 beds, 1 bath
Aug 16–21
4.95 out of 5 average rating, 172 reviews
Superhost
Cabin in Monterey
Secluded cabin with babbling brook
3 bedrooms, 3 beds, 1 bath
Oct 25–30
4.87 out of 5 average rating, 256 reviews
Guest favourite
Home in Sheffield
Bull Hill Bungalow
3 bedrooms, 3 beds, 2 baths
Sep 7–12
4.98 out of 5 average rating, 54 reviews
Guest favourite
Cabin in Great Barrington
Kenyon's Cabin
2 bedrooms, 4 beds, 1 bath
Aug 23–28
4.89 out of 5 average rating, 36 reviews
Guest favourite
Cabin in Great Barrington
Modern Luxury Log Cabin
4 bedrooms, 6 beds, 3 baths
Sep 21–26
4.97 out of 5 average rating, 115 reviews
Top guest favourite
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
3 bedrooms, 4 beds, 2 baths
Sep 20–25
4.99 out of 5 average rating, 313 reviews
Guest favourite
Cottage in Sheffield
Cheerful 3-bedroom cottage with woodstove.
3 bedrooms, 3 beds, 2.5 baths
Sep 13–18
4.92 out of 5 average rating, 192 reviews
Top guest favourite
Home in Great Barrington
Berkshires Black Abbey
3 bedrooms, 4 beds, 3 baths
Aug 23–28
5.0 out of 5 average rating, 40 reviews
Top guest favourite
Home in Monterey
Charming cottage w/ gorgeous views.
2 bedrooms, 2 beds, 2 baths
Sep 7–12
4.93 out of 5 average rating, 369 reviews