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Search results; Over 1,000 homes in Great Barrington

Top guest favourite
Guest suite in Great Barrington
Hillside Haven
1 bedroom, 2 beds, 1 private bathroom
7–12 Sept
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4.99 out of 5 average rating, 136 reviews
Guest favourite
Flat in Great Barrington
Berkshire Retreat|King Bed|Wi-Fi|2m Ski Resort
1 king bed
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
6–11 Sept
4.96 out of 5 average rating, 191 reviews
Guest favourite
Room in Great Barrington
Quiet refuge in Great Barrington
1 queen bed
14–19 Sept
4.92 out of 5 average rating, 241 reviews
Guest favourite
Treehouse in New Marlborough
Berkshire Treehouse Retreat
3 bedrooms, 4 beds
6–11 Sept
4.91 out of 5 average rating, 173 reviews
Top guest favourite
Room in Great Barrington
Large, light bedroom on The Hill (Eco Airbnb)
1 double bed
1–6 Sept
4.97 out of 5 average rating, 31 reviews
Top guest favourite
Home in Monterey
Charming cottage w/ gorgeous views.
2 bedrooms, 2 beds
7–12 Sept
4.93 out of 5 average rating, 370 reviews
Top guest favourite
Guest house in Stockbridge
Bitty Berkshire Bungalow
1 bedroom, 1 queen bed
4–9 Oct
4.98 out of 5 average rating, 58 reviews
Top guest favourite
Home in Great Barrington
Prime location for the best of the Berkshires
2 bedrooms, 2 queen beds
9–14 Sept
4.97 out of 5 average rating, 138 reviews
Superhost
Barn in Canaan
The Cobble Barn | Fireplace • A/C • Screened Porch
2 bedrooms, 3 beds
6–11 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms, 4 beds
7–12 Sept
4.89 out of 5 average rating, 9 reviews
Top guest favourite
Home in Great Barrington
Berkshires Black Abbey
3 bedrooms, 4 beds
8–13 Sept
5.0 out of 5 average rating, 43 reviews
Top guest favourite
Guest suite in Great Barrington
The Serendipity Spot
1 bedroom, 1 bed
5–10 Sept
4.95 out of 5 average rating, 55 reviews
Guest favourite
Cottage in Great Barrington
The Cottage at The Barrington House
1 bedroom, 1 queen bed
13–18 Sept
4.94 out of 5 average rating, 221 reviews
Top guest favourite
Flat in Great Barrington
Private En Suite in Beautiful Victorian
1 bedroom, 1 queen bed
26–31 Oct
4.95 out of 5 average rating, 425 reviews
Top guest favourite
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
3 bedrooms, 4 beds
20–25 Sept
4.99 out of 5 average rating, 314 reviews
Guest favourite
Guest house in Great Barrington
Berkshires Guest Barn
2 bedrooms, 5 beds
9–14 Sept
4.95 out of 5 average rating, 37 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
Top guest favourite
Home in Egremont
Modern Farmhouse 5 minutes from Great Barrington
2 bedrooms, 2 beds
7–12 Sept
5.0 out of 5 average rating, 11 reviews