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Search results; Over 1,000 homes in Great Barrington

Top guest favourite
Home in Great Barrington
Berkshires Black Abbey
3 bedrooms, 4 beds, 3 private bathrooms
8–13 Sept
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5.0 out of 5 average rating, 43 reviews
Guest favourite
Flat in Great Barrington
Berkshire Retreat|King Bed|Wi-Fi|2m Ski Resort
1 king bed, 1 bathroom
7–12 Sept
4.89 out of 5 average rating, 178 reviews
Guest favourite
Flat in Great Barrington
King Bed, Wi-Fi, 2m Ski Resort
1 king bed, 1 bathroom
6–11 Sept
4.96 out of 5 average rating, 191 reviews
Top guest favourite
Room in Great Barrington
Large, light bedroom on The Hill (Eco Airbnb)
1 double bed, 1 bathroom
1–6 Sept
4.97 out of 5 average rating, 31 reviews
Top guest favourite
Flat in Great Barrington
The River’s Whisper
2 bedrooms, 2 queen beds, 1 bathroom
28 Sept – 3 Oct
4.98 out of 5 average rating, 47 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, 45 reviews
Top guest favourite
Rooms in Town of Hillsdale
Bellwether on Main, Passive House & AAC
2 bedrooms, 2 queen beds, 2 bathrooms
6–11 Sept
5.0 out of 5 average rating, 7 reviews
Guest favourite
Room in Great Barrington
Quiet refuge in Great Barrington
1 queen bed, 1 bathroom
14–19 Sept
4.92 out of 5 average rating, 241 reviews
Guest favourite
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.89 out of 5 average rating, 9 reviews
Top guest favourite
Flat in Great Barrington
Walk Everywhere! | Relax in Easy Elegance!
2 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 145 reviews
Guest favourite
Cottage in Sheffield
Cheerful 3-bedroom cottage with woodstove.
3 bedrooms, 3 beds, 2.5 bathrooms
13–18 Sept
4.92 out of 5 average rating, 192 reviews
Guest favourite
Treehouse in New Marlborough
Berkshire Treehouse Retreat
3 bedrooms, 4 beds, WC
6–11 Sept
4.91 out of 5 average rating, 173 reviews
Top guest favourite
Room in Lee
Warm & Welcoming Room w/ Private Bath
1 queen bed, 1 bathroom
4–9 Sept
4.98 out of 5 average rating, 245 reviews
Superhost
Barn in Canaan
The Cobble Barn | Fireplace • A/C • Screened Porch
2 bedrooms, 3 beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Guest house in Stockbridge
Bitty Berkshire Bungalow
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.98 out of 5 average rating, 58 reviews
Top guest favourite
Loft in Great Barrington
The Nest 5 min walk to downtown Great Barrington
1 bedroom, 1 queen bed, 1 bathroom
20–25 Oct
5.0 out of 5 average rating, 64 reviews
Top guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
1 bedroom, 1 bed, 1 bathroom
25–30 Sept
4.99 out of 5 average rating, 329 reviews
Hotel room in Lee
Endless Family Fun: Pools, Arcade Room & Mini Golf
3 bedrooms, 2 bathrooms
6–11 Sept
4.68 out of 5 average rating, 28 reviews
Guest favourite
Flat in Great Barrington
Beautfiul, modern, GB apartment
1 bedroom, 1 double bed, 1 bathroom
12–17 Oct
4.81 out of 5 average rating, 303 reviews