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Search results; Over 1,000 homes in Great Barrington

Guest favourite
Cottage in Great Barrington
The Cottage at The Barrington House
1 bedroom, 1 bed, 1 private bathroom
22–27 Aug
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4.94 out of 5 average rating, 217 reviews
Guest favourite
Flat in Great Barrington
King Bed|ADA ROOM|2m Ski Resort
1 king bed, 1 bathroom
23–28 Aug
4.9 out of 5 average rating, 72 reviews
Home in Great Barrington
Garden Retreat, 1st fl KING ste, EV, close to all
3 bedrooms, 4 beds, 3 bathrooms
16–21 Aug
New place to stay
Top guest favourite
Flat in Great Barrington
The River’s Whisper
2 bedrooms, 2 queen beds, 1 bathroom
13–18 Oct
4.98 out of 5 average rating, 47 reviews
Home in Great Barrington
Cozy Riverside Retreat in the Berkshires
3 bedrooms, 4 beds, 1 bathroom
23–28 Aug
4.5 out of 5 average rating, 30 reviews
Guest favourite
Flat in Great Barrington
King Bed|Wi-Fi|2m Ski Resort|Berkshires
1 king bed, 1 bathroom
23–28 Aug
4.88 out of 5 average rating, 133 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
Loft in Great Barrington
The Old Red Barn
1 bedroom, 1 queen bed, 1 bathroom
8–13 Sept
4.99 out of 5 average rating, 367 reviews
Top guest favourite
Home in Great Barrington
Stunning luxury home with pool
4 bedrooms, 4 beds, 4.5 bathrooms
9–14 Sept
4.99 out of 5 average rating, 93 reviews
Top guest favourite
Home in Great Barrington
Sauna + Hot Tub Escape | Private & Pet Friendly
3 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 56 reviews
Top guest favourite
Cottage in Monterey
Beaver Lodge
3 bedrooms, 3 queen beds, 1.5 bathrooms
10–15 Sept
5.0 out of 5 average rating, 83 reviews
Guest favourite
Rooms in Town of Hillsdale
Bellwether on Main, Passive House & AAC
2 bedrooms, 2 queen beds, 2 bathrooms
19–24 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
2 bedrooms, 2 queen beds, 1 bathroom
14–19 Sept
4.99 out of 5 average rating, 69 reviews
Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
3 bedrooms, 4 beds, 1 bathroom
30 Aug – 4 Sept
4.95 out of 5 average rating, 172 reviews
Guest favourite
Home in Egremont
Nature Retreat Near Prospect Lake
3 bedrooms, 6 beds, 1 bathroom
31 Aug – 5 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Great Barrington
Prime location for the best of the Berkshires
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Sept
4.97 out of 5 average rating, 137 reviews
Guest favourite
Cottage in Egremont
Kayak on Prospect Lake, Paddle Boards, Swim Dock+!
3 bedrooms, 5 beds, 1 bathroom
12–17 Sept
4.98 out of 5 average rating, 55 reviews
Home in Great Barrington
Relaxed Berkshires Retreat Near Downtown GB
2 bedrooms, 2 beds, 1.5 bathrooms
4–9 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Guest house in Great Barrington
Berkshires Guest Barn
2 bedrooms, 5 beds, 1 bathroom
23–28 Aug
4.95 out of 5 average rating, 37 reviews