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Search results; Over 1,000 homes in Great Barrington

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Superhost
Chalet in Great Barrington
Sunset River Views, SIP, Spotless, Sleeps 8
3 bedrooms, 5 beds, 2.5 private bathrooms
27 Sept – 2 Oct
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4.86 out of 5 average rating, 22 reviews
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Guest favourite
Home in West Stockbridge
8 Mi to Tanglewood & Butternut Ski: Spacious Home!
6 bedrooms, 7 beds
1–6 Sept
4.88 out of 5 average rating, 25 reviews
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Guest favourite
Home in Great Barrington
A Berkshires Abode - Minutes to Ski & Downtown GB!
3 bedrooms, 4 beds
1–6 Sept
4.97 out of 5 average rating, 30 reviews
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Top guest favourite
Home in Great Barrington
Stunning luxury home with pool
4 bedrooms, 4 beds
9–14 Sept
4.99 out of 5 average rating, 94 reviews
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Guest favourite
Home in Great Barrington
Lovely house in the Berkshires
3 bedrooms, 4 beds
7–12 Sept
4.93 out of 5 average rating, 30 reviews
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Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
3 bedrooms, 4 beds
6–11 Sept
4.95 out of 5 average rating, 174 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
9–14 Sept
4.97 out of 5 average rating, 138 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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Superhost
Home in Great Barrington
Woodland - Stunning 5 bedroom home in GB!
5 bedrooms, 10 beds
27 Sept – 2 Oct
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Top guest favourite
Home in Great Barrington
Fall Foliage @ The Barrington House: GB
5 bedrooms, 6 beds
13–18 Sept
5.0 out of 5 average rating, 16 reviews
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Superhost
Home in Sheffield
Timber Frame • Big Deck • Game Room | Near Trails
4 bedrooms, 6 beds
8–13 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
13–18 Sept
5.0 out of 5 average rating, 59 reviews
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Top guest favourite
Home in Great Barrington
Modern Victorian- Walk to Town
4 bedrooms, 7 beds
14–19 Sept
4.97 out of 5 average rating, 142 reviews
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Guest favourite
Cottage in Sheffield
Cheerful 3-bedroom cottage with woodstove.
3 bedrooms, 3 beds
13–18 Sept
4.92 out of 5 average rating, 192 reviews
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Top guest favourite
Home in Monterey
Berkshires Retreat | Fall Foliage | Fenced Yard
5 bedrooms, 7 beds
6–11 Sept
5.0 out of 5 average rating, 49 reviews
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Top guest favourite
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
3 bedrooms, 4 beds
7–12 Sept
4.99 out of 5 average rating, 317 reviews
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Guest favourite
Flat in Great Barrington
King Bed|Wi-Fi|2m Ski Resort|Studio
1 king bed
7–12 Sept
4.83 out of 5 average rating, 115 reviews
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Guest favourite
Home in Great Barrington
Berkshires Retreat!
5 bedrooms, 9 beds
9–14 Sept
4.97 out of 5 average rating, 39 reviews
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Top guest favourite
Home in Great Barrington
Berkshires Black Abbey
3 bedrooms, 4 beds
8–13 Sept
5.0 out of 5 average rating, 45 reviews