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Search results; Over 1,000 homes in Great Barrington

Guest favourite
Home in Great Barrington
Never too early to book for the Holidays & NYE!
4 bedrooms, 5 beds, 2 private bathrooms
3–8 Sept
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4.91 out of 5 average rating, 139 reviews
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, 67 reviews
Top guest favourite
Flat in Great Barrington
King Bed | Patio | 2m to Ski Resort
1 king bed
23–28 Aug
4.91 out of 5 average rating, 173 reviews
Top guest favourite
Room in Great Barrington
Comfy single for a night or two (Eco Airbnb)
1 single bed
3–8 Aug
4.93 out of 5 average rating, 54 reviews
Top guest favourite
Room in Great Barrington
Large, light bedroom on The Hill (Eco Airbnb)
1 double bed
19–24 Aug
4.97 out of 5 average rating, 31 reviews
Top guest favourite
Room in Great Barrington
Cozy & Convenient
1 queen bed
9–14 Aug
5.0 out of 5 average rating, 50 reviews
Guest favourite
Flat in Great Barrington
Beautfiul, modern, GB apartment
1 bedroom, 1 double bed
12–17 Oct
4.81 out of 5 average rating, 302 reviews
Top guest favourite
Flat in Great Barrington
Private En Suite in Beautiful Victorian
1 bedroom, 1 queen bed
21–26 Oct
4.95 out of 5 average rating, 421 reviews
Top guest favourite
Room in Great Barrington
Quiet refuge in Great Barrington
1 queen bed
6–11 Sept
4.94 out of 5 average rating, 232 reviews
Top guest favourite
Flat in Great Barrington
Cozy, Quiet Apt. in Housatonic, Great Barrington
1 bedroom, 2 beds
22–27 Aug
5.0 out of 5 average rating, 38 reviews
Top guest favourite
Cottage in Great Barrington
Artist Cottage
1 bedroom, 1 queen bed
30 Aug – 4 Sept
4.93 out of 5 average rating, 348 reviews
Guest favourite
Home in Great Barrington
Hilltop Ski and Sun Chalet with Hot Tub
5 bedrooms, 6 beds
13–18 Sept
4.97 out of 5 average rating, 61 reviews
Top guest favourite
Home in Great Barrington
Stunning luxury home with pool
4 bedrooms, 4 beds
28 Sept – 3 Oct
4.99 out of 5 average rating, 92 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, 52 reviews
Top guest favourite
Guest suite in Great Barrington
The Serendipity Spot
1 bedroom, 1 bed
9–14 Aug
4.94 out of 5 average rating, 54 reviews
Top guest favourite
Guest suite in Great Barrington
Hillside Haven
1 bedroom, 2 beds
7–12 Sept
4.98 out of 5 average rating, 133 reviews
Top guest favourite
Home in Stockbridge
Bright Stockbridge country home, near everything!
2 bedrooms, 2 queen beds
13–18 Sept
4.95 out of 5 average rating, 185 reviews
Top guest favourite
Flat in Great Barrington
Secluded but not isolated Berkshire Retreat
2 bedrooms, 2 beds
9–14 Sept
4.93 out of 5 average rating, 211 reviews
Guest favourite
Room in Great Barrington
Art Studio
1 bed
9–14 Aug
4.96 out of 5 average rating, 28 reviews