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Search results; Over 1,000 homes in Great Barrington

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Top guest favourite
Loft in Great Barrington
The Old Red Barn
1 bedroom, 1 bed, 1 private bathroom
26–31 Oct
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4.99 out of 5 average rating, 371 reviews
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Top guest favourite
Cottage in Monterey
Beaver Lodge
3 bedrooms, 3 queen beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 83 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
10–15 Nov
4.97 out of 5 average rating, 141 reviews
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Top guest favourite
Cottage in Great Barrington
Carriage house with Chef's Kitchen, close to town
2 bedrooms, 3 beds
25–30 Oct
4.93 out of 5 average rating, 160 reviews
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Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
3 bedrooms, 4 beds
27 Sept – 2 Oct
4.95 out of 5 average rating, 176 reviews
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Home in Great Barrington
Riverside Retreat in the Berkshires
3 bedrooms, 4 beds
20–25 Sept
4.61 out of 5 average rating, 38 reviews
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Top guest favourite
Cottage in Great Barrington
Artist Cottage
1 bedroom, 1 queen bed
5–10 Nov
4.94 out of 5 average rating, 354 reviews
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Top guest favourite
Home in Great Barrington
Sauna + Hot Tub Escape | Private & Pet Friendly
3 bedrooms, 4 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 56 reviews
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Guest favourite
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms, 4 beds
19–24 Oct
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
20–25 Sept
4.91 out of 5 average rating, 178 reviews
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Top guest favourite
Guest house in Great Barrington
Trailside Cottage
1 bedroom, 3 beds
29 Oct – 3 Nov
5.0 out of 5 average rating, 17 reviews
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Guest favourite
Cottage in Sheffield
Cheerful 3-bedroom cottage with woodstove.
3 bedrooms, 3 beds
24–29 Oct
4.92 out of 5 average rating, 195 reviews
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Guest favourite
Home in Great Barrington
Sunsets On Blue Hill, Newly Renovated Farmhouse
4 bedrooms, 6 beds
4–9 Oct
4.94 out of 5 average rating, 84 reviews
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Top guest favourite
Home in Great Barrington
Fall Foliage @ The Barrington House: GB
5 bedrooms, 6 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 18 reviews
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Top guest favourite
Home in Great Barrington
Berkshires Black Abbey
3 bedrooms, 4 beds
20–25 Sept
5.0 out of 5 average rating, 47 reviews
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Top guest favourite
Home in Great Barrington
Country Castle-Complete privacy-minutes from town
6 bedrooms, 9 beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 68 reviews
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Guest favourite
Home in Great Barrington
Berkshire’s Best-hottub-fitness/gameroom
4 bedrooms, 4 beds
20–25 Sept
4.92 out of 5 average rating, 25 reviews
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Guest favourite
Home in Great Barrington
Lovely house in the Berkshires
3 bedrooms, 4 beds
21–26 Sept
4.87 out of 5 average rating, 31 reviews
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Home in Great Barrington
Mountain Views + Scenic Berkshires Hideaway
3 bedrooms, 6 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 3 reviews