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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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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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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
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms, 4 beds, 2 bathrooms
19–24 Sept
4.9 out of 5 average rating, 10 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
19–24 Sept
New place to stay
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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
Photo 1 of 29
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
25–30 Oct
4.93 out of 5 average rating, 160 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
Walk to Town! Great Barrington 4-bedroom farmhouse
4 bedrooms, 4 beds, 2 bathrooms
26–31 Oct
5.0 out of 5 average rating, 116 reviews
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Guest favourite
Home in Great Barrington
Never too early to book for the Holidays & NYE!
4 bedrooms, 5 beds, 2 bathrooms
8–13 Oct
4.91 out of 5 average rating, 142 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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Guest favourite
Flat in Great Barrington
King Bed |Wi-Fi| 2m to Ski Resort
1 king bed, 1 bathroom
4–9 Oct
4.92 out of 5 average rating, 222 reviews
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Guest favourite
Cabin in Great Barrington
Kenyon's Cabin
2 bedrooms, 4 beds, 1 bathroom
19–24 Sept
4.87 out of 5 average rating, 38 reviews
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Top guest favourite
Loft in Great Barrington
The Old Red Barn
1 bedroom, 1 queen bed, 1 bathroom
26–31 Oct
4.99 out of 5 average rating, 371 reviews
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Top guest favourite
Guest house in Stockbridge
Bitty Berkshire Bungalow
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.98 out of 5 average rating, 61 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
Cottage in Great Barrington
Cottage on Scenic Road
1 bedroom, 1 queen bed, 1 bathroom
28 Sept – 3 Oct
4.91 out of 5 average rating, 281 reviews