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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, 214 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, 67 reviews
Top guest favourite
Loft in Great Barrington
The Old Red Barn
1 bedroom, 1 queen bed, 1 bathroom
10–15 Aug
4.99 out of 5 average rating, 365 reviews
Guest favourite
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.88 out of 5 average rating, 8 reviews
Top guest favourite
Barn in New Marlborough
Hartsville Barn in the Berkshires
2 bedrooms, 2 king beds, 1 bathroom
27 Oct – 1 Nov
4.98 out of 5 average rating, 42 reviews
Guest favourite
Flat in Great Barrington
King Bed|Berkshires|2m Ski Resort|Patio|Wi-Fi
1 king bed, 1 bathroom
23–28 Aug
4.88 out of 5 average rating, 165 reviews
Guest favourite
Tiny home in New Marlborough
Bedroom Forest View I Sauna I Fire-pit I Trails
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
4.94 out of 5 average rating, 186 reviews
Top guest favourite
Cottage in Great Barrington
Artist Cottage
1 bedroom, 1 queen bed, 2 bathrooms
25–30 Aug
4.93 out of 5 average rating, 347 reviews
Top guest favourite
Home in Great Barrington
Stunning luxury home with pool
4 bedrooms, 4 beds, 4.5 bathrooms
23–28 Sept
4.99 out of 5 average rating, 92 reviews
Top guest favourite
Guest house in Great Barrington
Berkshires Guest Barn
2 bedrooms, 5 beds, 1 bathroom
10–15 Aug
4.97 out of 5 average rating, 33 reviews
Guest favourite
Cottage in Egremont
Kayak on Prospect Lake, Paddle Boards, Swim Dock+!
3 bedrooms, 5 beds, 1 bathroom
2–7 Aug
4.98 out of 5 average rating, 53 reviews
Guest favourite
Home in Sheffield
Bull Hill Bungalow
3 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
4.98 out of 5 average rating, 54 reviews
Home in Great Barrington
Cottage by the Lake | Hiking, Skiing & Attractions
2 bedrooms, 4 beds, 1 bathroom
24–29 Aug
Guest favourite
Home in Great Barrington
Never too early to book for the Holidays & NYE!
4 bedrooms, 5 beds, 2 bathrooms
3–8 Sept
4.91 out of 5 average rating, 139 reviews
Guest favourite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
2 bedrooms, 2 queen beds, 1 bathroom
27 Aug – 1 Sept
4.99 out of 5 average rating, 67 reviews
Superhost
Cabin in Monterey
Secluded cabin with babbling brook
3 bedrooms, 3 beds, 1 bathroom
9–14 Sept
4.87 out of 5 average rating, 256 reviews
Home in Egremont
Nature Retreat Near Prospect Lake
3 bedrooms, 6 beds, 1 bathroom
17–22 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Cabin in Mount Washington
Chic Cabin in the Berkshires, Mountain getaway!
4 bedrooms, 2 queen beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Flat in Lee
Eliza Suite
1 bedroom, 1 bed, 1 bathroom
14–19 Sept
4.97 out of 5 average rating, 29 reviews