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Search results; Over 1,000 homes in Great Barrington

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Guest favourite
Holiday home in Great Barrington
Home in Great Barrington. Steps from downtown!
2 bedrooms, 3 beds, 1 private bathroom
25–30 Oct
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4.94 out of 5 average rating, 295 reviews
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Guest favourite
Cottage in Sheffield
Cheerful 3-bedroom cottage with woodstove.
3 bedrooms, 3 beds, 2.5 bathrooms
20–25 Sept
4.92 out of 5 average rating, 195 reviews
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Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
3 bedrooms, 4 beds, 1 bathroom
27 Sept – 2 Oct
4.95 out of 5 average rating, 176 reviews
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Top guest favourite
Home in Monterey
Berkshires Retreat | Fall Foliage | Fenced Yard
5 bedrooms, 7 beds, 3.5 bathrooms
18–23 Sept
5.0 out of 5 average rating, 49 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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Top guest favourite
Home in Great Barrington
Berkshires Black Abbey
3 bedrooms, 4 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 47 reviews
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Room in Great Barrington
Gracious Private Room & Bath in the Berkshires
1 queen bed, 1.5 bathrooms
18–23 Sept
New place to stay
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Top guest favourite
Cottage in Great Barrington
Carriage house with Chef's Kitchen, close to town
2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
4.93 out of 5 average rating, 160 reviews
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Guest favourite
Home in Great Barrington
Lovely house in the Berkshires
3 bedrooms, 4 beds, 1.5 bathrooms
19–24 Sept
4.87 out of 5 average rating, 31 reviews
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Guest favourite
Chalet in Great Barrington
Berkshire "Zen" Cottage
3 bedrooms, 4 beds, 2 bathrooms
19–24 Sept
4.94 out of 5 average rating, 88 reviews
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Top guest favourite
Cottage in Monterey
Beaver Lodge
3 bedrooms, 3 queen beds, 1.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 83 reviews
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Guest favourite
Home in Great Barrington
Berkshire’s Best-hottub-fitness/gameroom
4 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.92 out of 5 average rating, 25 reviews
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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, 51 reviews
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Guest favourite
Home in Great Barrington
Great Barrington, Cabin Sleeps 14, Walk To Town
3 bedrooms, 6 beds, 2.5 bathrooms
27 Sept – 2 Oct
4.85 out of 5 average rating, 138 reviews
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Superhost
Home in Great Barrington
Prime Location, Recently Redesigned, Riverfront!
4 bedrooms, 6 beds, 2 bathrooms
19–24 Sept
4.9 out of 5 average rating, 10 reviews
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Guest favourite
Flat in Great Barrington
King Bed | Stylish | Wi-Fi | *2m Ski Resort*
1 king bed, 1 bathroom
20–25 Sept
4.91 out of 5 average rating, 176 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
10–15 Nov
4.97 out of 5 average rating, 141 reviews
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Guest favourite
Flat in Great Barrington
Kitchenette|King Bed|Couch
1 bedroom, 1 king bed, 1 bathroom
27 Sept – 2 Oct
4.89 out of 5 average rating, 189 reviews
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Top guest favourite
Home in Lee
Berkshire 4 season home
3 bedrooms, 3 queen beds, 2 bathrooms
1–6 Nov
4.98 out of 5 average rating, 252 reviews