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Search results; Over 1,000 homes in Great Barrington

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Top guest favourite
Flat in Great Barrington
King Bed, Wi-Fi, 2m Ski Resort
Studio, 1 bed, 1 private bathroom
19–24 Sept
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4.96 out of 5 average rating, 197 reviews
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Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
3 bedrooms, 4 beds, 1 bathroom
11–16 Sept
4.95 out of 5 average rating, 174 reviews
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Top guest favourite
Home in Great Barrington
Fall Foliage @ The Barrington House: GB
5 bedrooms, 6 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 17 reviews
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Top guest favourite
Home in Great Barrington
The Yellow Victorian With Chefs Kitchen
3 bedrooms, 4 beds, 3.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 59 reviews
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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
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Guest favourite
Home in Great Barrington
Lovely house in the Berkshires
3 bedrooms, 4 beds, 1.5 bathrooms
7–12 Sept
4.87 out of 5 average rating, 31 reviews
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Guest favourite
Cottage in Sheffield
Cheerful 3-bedroom cottage with woodstove.
3 bedrooms, 3 beds, 2.5 bathrooms
13–18 Sept
4.92 out of 5 average rating, 192 reviews
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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, 94 reviews
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Top guest favourite
Home in Great Barrington
A Berkshires Abode - Minutes to Ski & Downtown GB!
3 bedrooms, 4 beds, 3 bathrooms
1–6 Sept
4.97 out of 5 average rating, 31 reviews
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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, 139 reviews
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Guest favourite
Home in Great Barrington
Berkshires Retreat!
5 bedrooms, 9 beds, 2.5 bathrooms
9–14 Sept
4.97 out of 5 average rating, 39 reviews
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Cottage in Sheffield
Charming Handcrafted Cottage in the Berkshires!
3 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
4.78 out of 5 average rating, 101 reviews
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Superhost
Home in Sheffield
Timber Frame • Big Deck • Game Room | Near Trails
4 bedrooms, 6 beds, 4 bathrooms
8–13 Sept
New place to stay
Photo 1 of 29
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
Photo 1 of 29
Top guest favourite
Home in Great Barrington
Berkshires Black Abbey
3 bedrooms, 4 beds, 3 bathrooms
8–13 Sept
5.0 out of 5 average rating, 45 reviews
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Superhost
Home in Great Barrington
Woodland - Stunning 5 bedroom home in GB!
5 bedrooms, 10 beds, 3 bathrooms
27 Sept – 2 Oct
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Top guest favourite
Chalet in Great Barrington
Berkshire "Zen" Cottage
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.95 out of 5 average rating, 87 reviews
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Top guest favourite
Home in Sheffield
Belle Meade
2 bedrooms, 2 beds, 2 bathrooms
1–6 Dec
4.99 out of 5 average rating, 133 reviews
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Guest favourite
Home in Great Barrington
Berkshires Family Oasis with Hot Tub, Patio, Gym
4 bedrooms, 7 beds, 2.5 bathrooms
7–12 Sept
4.98 out of 5 average rating, 50 reviews