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Search results; Over 1,000 homes in Great Barrington

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Guest favourite
Cottage in Great Barrington
The Cottage at The Barrington House
1 bedroom, 1 bed, 1 private bathroom
20–25 Sept
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4.93 out of 5 average rating, 224 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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Top guest favourite
Cottage in Great Barrington
Carriage house with Chef's Kitchen, close to town
2 bedrooms, 3 beds, 1.5 bathrooms
22–27 Oct
4.93 out of 5 average rating, 158 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
Flat in Great Barrington
King Bed | Patio | 2m to Ski Resort
1 king bed, 1 bathroom
20–25 Sept
4.92 out of 5 average rating, 183 reviews
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Room in Great Barrington
Gracious Private Room & Bath in the Berkshires
1 queen bed, 1.5 bathrooms
17–22 Sept
New place to stay
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Top guest favourite
Home in Great Barrington
Modern Victorian- Walk to Town
4 bedrooms, 7 beds, 2.5 bathrooms
18–23 Oct
4.97 out of 5 average rating, 142 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
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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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
Home in Great Barrington
Lovely house in the Berkshires
3 bedrooms, 4 beds, 1.5 bathrooms
18–23 Sept
4.87 out of 5 average rating, 31 reviews
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Guest favourite
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms, 4 beds, 2 bathrooms
17–22 Sept
4.9 out of 5 average rating, 10 reviews
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Guest favourite
Chalet in Great Barrington
Berkshire "Zen" Cottage
3 bedrooms, 4 beds, 2 bathrooms
18–23 Sept
4.94 out of 5 average rating, 88 reviews
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Guest favourite
Flat in Great Barrington
Berkshire Retreat|King Bed|Wi-Fi|2m Ski Resort
1 king bed, 1 bathroom
27 Sept – 2 Oct
4.89 out of 5 average rating, 188 reviews
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Top guest favourite
Flat in Great Barrington
The River’s Whisper
2 bedrooms, 2 queen beds, 1 bathroom
28 Sept – 3 Oct
4.98 out of 5 average rating, 51 reviews
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Guest favourite
Holiday home in Great Barrington
Home in Great Barrington. Steps from downtown!
2 bedrooms, 3 beds, 1 bathroom
25–30 Oct
4.94 out of 5 average rating, 294 reviews
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Top guest favourite
Loft in Great Barrington
The Nest 5 min walk to downtown Great Barrington
1 bedroom, 1 queen bed, 1 bathroom
2–7 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 bedrooms, 2 king beds, 1 bathroom
27 Oct – 1 Nov
4.98 out of 5 average rating, 50 reviews
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Top guest favourite
Home in Great Barrington
Seekonk Hill
2 bedrooms, 2 queen beds, 2 bathrooms
26–31 Oct
4.98 out of 5 average rating, 48 reviews