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Search results; Over 1,000 homes in Great Barrington

Top guest favourite
Home in Great Barrington
Stunning luxury home with pool
4 bedrooms, 4 beds, 4.5 private bathrooms
9–14 Sept
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4.99 out of 5 average rating, 94 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, 190 reviews
Top guest favourite
Place to stay in Stockbridge
Cozy room w/private bath–near Tanglewood/Kripalu
1 bedroom, 1 bed, 1 bathroom
13–18 Sept
4.85 out of 5 average rating, 163 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
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
4.93 out of 5 average rating, 239 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
Home in Great Barrington
Seekonk Hill
2 bedrooms, 2 beds, 2 bathrooms
26–31 Oct
4.98 out of 5 average rating, 45 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
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
Guest favourite
Cottage in Great Barrington
The Cottage at The Barrington House
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
4.94 out of 5 average rating, 220 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
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
Guest favourite
Treehouse in New Marlborough
Berkshire Treehouse Retreat
3 bedrooms, 4 beds, WC
6–11 Sept
4.91 out of 5 average rating, 172 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, 328 reviews
Guest favourite
Guest house in Great Barrington
1-bed unit 3/4 mi. from GB dwntwn.
1 bedroom, 1 king bed, 1 bathroom
2–7 Sept
4.86 out of 5 average rating, 79 reviews
Flat in Egremont
Berkshires Charm Private Apartment
1 bedroom, 1 queen bed, 1 bathroom
18–23 Oct
New place to stay
Top guest favourite
Guest house in Great Barrington
Trailside Cottage
1 bedroom, 3 beds, 1 bathroom
28 Sept – 3 Oct
5.0 out of 5 average rating, 15 reviews