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Search results; Over 1,000 homes in Great Barrington

Top guest favourite
Flat in Great Barrington
Walk Everywhere! | Relax in Easy Elegance!
2 bedrooms, 3 beds, 2 private bathrooms
3–8 Sept
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5.0 out of 5 average rating, 145 reviews
Flat in Egremont
Berkshires Charm Private Apartment
1 bedroom, 1 queen bed
23–28 Aug
New place to stay
Guest favourite
Flat in Great Barrington
King Bed|ADA ROOM|2m Ski Resort
1 king bed
23–28 Aug
4.9 out of 5 average rating, 73 reviews
Top guest favourite
Cottage in Great Barrington
Artist Cottage
1 bedroom, 1 queen bed
30 Oct – 4 Nov
4.93 out of 5 average rating, 351 reviews
Top guest favourite
Loft in Great Barrington
The Old Red Barn
1 bedroom, 1 queen bed
8–13 Sept
4.99 out of 5 average rating, 367 reviews
Top guest favourite
Flat in Great Barrington
The River’s Whisper
2 bedrooms, 2 queen beds
28 Sept – 3 Oct
4.98 out of 5 average rating, 47 reviews
Top guest favourite
Room in North Chatham
Charming Eyebrow Colonial North Chatham, NY
1 king bed
30 Aug – 4 Sept
4.97 out of 5 average rating, 620 reviews
Guest favourite
Cottage in Great Barrington
The Cottage at The Barrington House
1 bedroom, 1 queen bed
22–27 Aug
4.94 out of 5 average rating, 217 reviews
Guest favourite
Cottage in Sheffield
Cheerful 3-bedroom cottage with woodstove.
3 bedrooms, 3 beds
13–18 Sept
4.92 out of 5 average rating, 192 reviews
Superhost
Barn in Canaan
The Cobble Barn | Fireplace • A/C • Screened Porch
2 bedrooms, 3 beds
30 Aug – 4 Sept
New place to stay
Guest favourite
Flat in Great Barrington
King Bed, Wi-Fi, 2m Ski Resort
1 king bed
22–27 Aug
4.96 out of 5 average rating, 189 reviews
Guest favourite
Home in Sheffield
Bull Hill Bungalow
3 bedrooms, 3 beds
7–12 Sept
4.98 out of 5 average rating, 55 reviews
Guest favourite
Room in Town of Ancram
The Doodletown
1 double bed
22–27 Sept
4.96 out of 5 average rating, 215 reviews
Top guest favourite
Place to stay in Stockbridge
Cozy room w/private bath–near Tanglewood/Kripalu
1 bedroom, 1 bed
23–28 Aug
4.85 out of 5 average rating, 163 reviews
Top guest favourite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
2 bedrooms, 2 queen beds
14–19 Sept
4.99 out of 5 average rating, 69 reviews
Top guest favourite
Home in Great Barrington
Seekonk Hill
2 bedrooms, 2 beds
26–31 Oct
4.98 out of 5 average rating, 44 reviews
Top guest favourite
Chalet in Otis
Mid-Century Glass Octagon in the Berkshires
1 bedroom, 2 beds
13–18 Sept
4.95 out of 5 average rating, 481 reviews
Superhost
Cabin in Monterey
Secluded cabin with babbling brook
3 bedrooms, 3 beds
2–7 Nov
4.87 out of 5 average rating, 256 reviews
Top guest favourite
Home in Great Barrington
Berkshires Black Abbey
3 bedrooms, 4 beds
23–28 Aug
5.0 out of 5 average rating, 40 reviews