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Search results; Over 1,000 homes in Great Barrington

Top guest favourite
Cottage in Great Barrington
Artist Cottage
1 bedroom, 1 bed, 2 private bathrooms
2–7 Aug
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4.93 out of 5 average rating, 346 reviews
Guest favourite
Flat in Great Barrington
King Bed | Stylish | Wi-Fi | *2m Ski Resort*
4.91 out of 5 average rating, 150 reviews, 1 bed, 1 bathroom
26–31 Jul
Home in Town of Hillsdale
Secluded 19-Acre Hudson Valley Escape w/ Pool
New place to stay, 3 bedrooms, 6 beds, 2.5 bathrooms
12–17 Aug
Top guest favourite
Loft in Great Barrington
The Old Red Barn
4.99 out of 5 average rating, 364 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 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
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
Cabin in Great Barrington
Modern Luxury Log Cabin
4.96 out of 5 average rating, 114 reviews, 4 bedrooms, 6 beds, 3 bathrooms
23–28 Aug
Guest favourite
Home in Egremont
24 Main - The Egremont Village House
5.0 out of 5 average rating, 23 reviews, 7 bedrooms, 7 beds, 4.5 bathrooms
12–17 Aug
Top guest favourite
Home in Great Barrington
Private Home in The Berkshires (New Hot Tub!)
4.99 out of 5 average rating, 125 reviews, 2 bedrooms, 2 beds, 1 bathroom
2–7 Dec
Top guest favourite
Guest suite in Great Barrington
The Serendipity Spot
4.94 out of 5 average rating, 53 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 Jul
Top guest favourite
Home in Great Barrington
Walk to Town! Great Barrington 4-bedroom farmhouse
5.0 out of 5 average rating, 111 reviews, 4 bedrooms, 4 beds, 2 bathrooms
13–18 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
Home in Egremont
Nature Retreat Near Prospect Lake
New place to stay, 3 bedrooms, 6 beds, 1 bathroom
9–14 Aug
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
Bungalow in Egremont
3-bedroom Berkshire bungalow on 2.5 peaceful acres
4.99 out of 5 average rating, 134 reviews, 3 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
Top guest favourite
Cabin in Mount Washington
Chic Cabin in the Berkshires, Mountain getaway!
5.0 out of 5 average rating, 7 reviews, 4 bedrooms, 2 beds, 1 bathroom
27 Jul – 1 Aug
Home in Great Barrington
Spacious and Rustic retreat in the Berkshires
4 bedrooms, 6 beds, 2.5 bathrooms
28 Sept – 3 Oct
Top guest favourite
Home in Great Barrington
The Yellow Victorian With Chefs Kitchen
5.0 out of 5 average rating, 55 reviews, 3 bedrooms, 4 beds, 3.5 bathrooms
25–30 Aug
Superhost
Cabin in Monterey
Secluded cabin with babbling brook
4.87 out of 5 average rating, 255 reviews, 3 bedrooms, 3 beds, 1 bathroom
9–14 Sept