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Search results; Over 1,000 homes in Great Barrington

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Top guest favourite
Cottage in Great Barrington
Artist Cottage
1 bedroom, 1 bed, 2 private bathrooms
16–21 Nov
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4.94 out of 5 average rating, 354 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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Guest favourite
Treehouse in New Marlborough
Berkshire Treehouse Retreat
3 bedrooms, 4 beds, WC
21–26 Sept
4.91 out of 5 average rating, 180 reviews
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Top guest favourite
Home in Great Barrington
Stunning luxury home with pool
4 bedrooms, 4 beds, 4.5 bathrooms
19–24 Oct
4.99 out of 5 average rating, 95 reviews
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Guest favourite
Home in Great Barrington
Spacious and Rustic retreat in the Berkshires
4 bedrooms, 6 beds, 2.5 bathrooms
16–21 Apr
5.0 out of 5 average rating, 7 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
The Yellow Victorian With Chefs Kitchen
3 bedrooms, 4 beds, 3.5 bathrooms
17–22 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
Cabin in Great Barrington
Kenyon's Cabin
2 bedrooms, 4 beds, 1 bathroom
18–23 Sept
4.87 out of 5 average rating, 38 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
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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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
Cottage in Great Barrington
The Cottage at The Barrington House
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.93 out of 5 average rating, 224 reviews
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Top guest favourite
Home in Great Barrington
RENOVATED BERKSHIRE COUNTRY CASTLE
3 bedrooms, 3 beds, 3 bathrooms
25–30 Sept
4.97 out of 5 average rating, 58 reviews
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Guest favourite
Home in Great Barrington
Hilltop Ski and Sun Chalet with Hot Tub
5 bedrooms, 6 beds, 3.5 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 63 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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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
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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Top guest favourite
Cottage in Great Barrington
Cottage on Scenic Road
1 bedroom, 1 queen bed, 1 bathroom
18–23 Sept
4.91 out of 5 average rating, 281 reviews