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Search results; Over 1,000 homes in Great Barrington

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Guest favourite
Chalet in Great Barrington
Berkshire "Zen" Cottage
3 bedrooms, 4 beds, 2 private bathrooms
19–24 Sept
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4.94 out of 5 average rating, 88 reviews
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Top guest favourite
Cottage in Great Barrington
Carriage house with Chef's Kitchen, close to town
3 beds
25–30 Oct
4.93 out of 5 average rating, 160 reviews
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Top guest favourite
Flat in Great Barrington
King Bed | Patio | 2m to Ski Resort
1 king bed
20–25 Sept
4.92 out of 5 average rating, 183 reviews
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Top guest favourite
Cottage in Great Barrington
Artist Cottage
1 queen bed
5–10 Nov
4.94 out of 5 average rating, 354 reviews
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Room in Great Barrington
Stay with Nelson
Gracious Private Room & Bath in the Berkshires
18–23 Sept
New place to stay
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Guest favourite
Cottage in Sheffield
Cheerful 3-bedroom cottage with woodstove.
3 beds
20–25 Sept
4.92 out of 5 average rating, 195 reviews
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Top guest favourite
Home in Great Barrington
Modern Victorian- Walk to Town
7 beds
18–23 Oct
4.97 out of 5 average rating, 142 reviews
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Guest favourite
Home in Great Barrington
Never too early to book for the Holidays & NYE!
5 beds
8–13 Oct
4.91 out of 5 average rating, 142 reviews
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Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
4 beds
27 Sept – 2 Oct
4.95 out of 5 average rating, 176 reviews
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Top guest favourite
Home in Great Barrington
Sauna + Hot Tub Escape | Private & Pet Friendly
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
Sunsets On Blue Hill, Newly Renovated Farmhouse
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
Prime location for the best of the Berkshires
2 queen beds
10–15 Nov
4.97 out of 5 average rating, 141 reviews
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Top guest favourite
Loft in Great Barrington
The Nest 5 min walk to downtown Great Barrington
1 queen bed
4–9 Oct
5.0 out of 5 average rating, 65 reviews
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Top guest favourite
Barn in New Marlborough
Hartsville Barn in the Berkshires
2 king beds
27 Oct – 1 Nov
4.98 out of 5 average rating, 51 reviews
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Guest favourite
Home in Great Barrington
Lovely house in the Berkshires
4 beds
19–24 Sept
4.87 out of 5 average rating, 31 reviews
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Top guest favourite
Cottage in Monterey
Beaver Lodge
3 queen beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 83 reviews
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Top guest favourite
Guest house in Great Barrington
Trailside Cottage
3 beds
29 Oct – 3 Nov
5.0 out of 5 average rating, 17 reviews
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Top guest favourite
Home in Great Barrington
Berkshires Black Abbey
4 beds
20–25 Sept
5.0 out of 5 average rating, 47 reviews
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Guest favourite
Treehouse in New Marlborough
Berkshire Treehouse Retreat
4 beds
21–26 Sept
4.91 out of 5 average rating, 180 reviews