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Search results; Over 1,000 homes in Great Barrington

Top guest favourite
Loft in Great Barrington
The Old Red Barn
1 bedroom, 1 bed, 1 private bathroom
10–15 Aug
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4.99 out of 5 average rating, 364 reviews
Home in Town of Hillsdale
Secluded 19-Acre Hudson Valley Escape w/ Pool
New place to stay, 3 bedrooms, 6 beds, 2.5 bathrooms
16–21 Aug
Home in Great Barrington
Garden Retreat, 1st fl KING ste, EV, close to all
New place to stay, 3 bedrooms, 4 beds, 3 bathrooms
4–9 Aug
Top guest favourite
Flat in Great Barrington
King Bed | Patio | 2m to Ski Resort
4.91 out of 5 average rating, 168 reviews, 1 bed, 1 bathroom
19–24 Aug
Top guest favourite
Flat in Great Barrington
King Bed |Wi-Fi| 2m to Ski Resort
4.92 out of 5 average rating, 208 reviews, 1 bed, 1 bathroom
22–27 Aug
Top guest favourite
Barn in New Marlborough
Hartsville Barn in the Berkshires
4.98 out of 5 average rating, 42 reviews, 2 bedrooms, 2 beds, 1 bathroom
14–19 Sept
Home in Egremont
Nature Retreat Near Prospect Lake
3 bedrooms, 6 beds, 1 bathroom
9–14 Aug
Top guest favourite
Flat in Great Barrington
Private En Suite in Beautiful Victorian
4.95 out of 5 average rating, 418 reviews, 1 bedroom, 1 bed, 1 bathroom
21–26 Oct
Guest favourite
Home in Great Barrington
In the middle of it all
4.93 out of 5 average rating, 15 reviews, 3 bedrooms, 4 beds, 3.5 bathrooms
7–12 Aug
Top guest favourite
Home in Great Barrington
Stunning luxury home with pool
4.99 out of 5 average rating, 92 reviews, 4 bedrooms, 4 beds, 4.5 bathrooms
2–7 Aug
Guest favourite
Tiny home in New Marlborough
Bedroom Forest View I Sauna I Fire-pit I Trails
4.94 out of 5 average rating, 182 reviews, 2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
Guest favourite
Home in Great Barrington
Great Barrington Lakeside Getaway w/ Kayak & Grill
4.83 out of 5 average rating, 41 reviews, 4 bedrooms, 6 beds, 4 bathrooms
10–15 Sept
Top guest favourite
Guest suite in Great Barrington
The Serendipity Spot
4.94 out of 5 average rating, 54 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Top guest favourite
Home in Egremont
The Catamount Ski Haus with Pool & Hot Tub
5.0 out of 5 average rating, 68 reviews, 4 bedrooms, 4 beds, 4 bathrooms
7–12 Sept
Guest favourite
Home in Great Barrington
Due to cancellation - a rare summer week is open!
4.91 out of 5 average rating, 137 reviews, 4 bedrooms, 5 beds, 2 bathrooms
3–8 Sept
Guest favourite
Home in Great Barrington
Berkshires Retreat!
4.97 out of 5 average rating, 37 reviews, 5 bedrooms, 9 beds, 2.5 bathrooms
9–14 Sept
Top guest favourite
Home in Great Barrington
GB at your doorstep
4.95 out of 5 average rating, 134 reviews, 3 bedrooms, 4 beds, 2 bathrooms
31 Aug – 5 Sept
Home in Great Barrington
Designed for Family Life
New place to stay, 4 bedrooms, 4 beds, 3 bathrooms
1–8 Oct
Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
4.95 out of 5 average rating, 170 reviews, 3 bedrooms, 4 beds, 1 bathroom
30 Aug – 4 Sept