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Search results; Over 1,000 homes in Great Barrington

Top guest favourite
Guest suite in Great Barrington
Hillside Haven
1 bedroom, 2 beds, 1 private bathroom
19–24 Jul
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4.98 out of 5 average rating, 128 reviews
Guest favourite
Flat in Great Barrington
King Bed, Wi-Fi, 2m Ski Resort
1 king bed, 1 bathroom
5–10 Jul
4.95 out of 5 average rating, 176 reviews
Superhost
Home in Monterey
Dog-Friendly Berkshires Retreat w/Fenced Yard
3 bedrooms, 3 beds, 2.5 bathrooms
28 Jul – 2 Aug
New place to stay
Top guest favourite
Home in Sheffield
Family friendly house with fenced yard & fire pit
3 bedrooms, 3 beds, 2 bathrooms
11–16 Jul
4.96 out of 5 average rating, 23 reviews
Top guest favourite
Home in Great Barrington
Private Home in The Berkshires (New Hot Tub!)
2 bedrooms, 2 queen beds, 1 bathroom
18–23 Jul
4.99 out of 5 average rating, 124 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, 132 reviews
Guest favourite
Flat in Great Barrington
Kitchenette|King Bed|Couch
1 bedroom, 1 king bed, 1 bathroom
23–28 Aug
4.89 out of 5 average rating, 180 reviews
Top guest favourite
Flat in Great Barrington
Walk Everywhere! | Relax in Easy Elegance!
2 bedrooms, 3 beds, 2 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 142 reviews
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Lee
Berkshire 4 season home
3 bedrooms, 3 queen beds, 2 bathrooms
25–30 Oct
4.98 out of 5 average rating, 248 reviews
Guest favourite
Guest suite in Great Barrington
The Serendipity Spot
1 bedroom, 1 bed, 1 bathroom
19–24 Jul
4.94 out of 5 average rating, 52 reviews
Top guest favourite
Home in Great Barrington
Walt's Townhouse - Berkshire living at its best
3 bedrooms, 3 beds, 2 bathrooms
13–18 Oct
5.0 out of 5 average rating, 83 reviews
Top guest favourite
Cabin in Great Barrington
Modern Luxury Log Cabin
4 bedrooms, 6 beds, 3 bathrooms
19–24 Jul
4.96 out of 5 average rating, 111 reviews
Guest favourite
Tiny home in New Marlborough
Bedroom Forest View I Sauna I Fire-pit I Trails
2 bedrooms, 2 beds, 1 bathroom
28 Jul – 2 Aug
4.94 out of 5 average rating, 174 reviews
Top guest favourite
Home in Great Barrington
Country Castle-Complete privacy-minutes from town
6 bedrooms, 8 beds, 3 bathrooms
4–9 Jul
4.98 out of 5 average rating, 61 reviews
Guest favourite
Home in Great Barrington
Berkshires Retreat!
5 bedrooms, 9 beds, 2.5 bathrooms
9–14 Sept
5.0 out of 5 average rating, 35 reviews
Top guest favourite
Room in Great Barrington
Quiet refuge in Great Barrington
1 queen bed, 1 bathroom
6–11 Sept
4.94 out of 5 average rating, 224 reviews
Guest favourite
Home in Great Barrington
River Cottage: Riverfront Home, Walkable Community
3 bedrooms, 3 beds, 2 bathrooms
30 Aug – 4 Sept
4.95 out of 5 average rating, 61 reviews
Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
3 bedrooms, 4 beds, 1 bathroom
12–17 Jul
4.96 out of 5 average rating, 165 reviews