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Search results; Over 1,000 homes in Great Barrington

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Top guest favourite
Guest suite in Great Barrington
Hillside Haven
1 bedroom, 2 beds, 1 private bathroom
7–12 Sept
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4.99 out of 5 average rating, 137 reviews
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Flat in Great Barrington
King Bed | Patio | 2m to Ski Resort
1 king bed, 1 bathroom
6–11 Sept
4.92 out of 5 average rating, 179 reviews
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Flat in Great Barrington
King Bed |Wi-Fi| 2m to Ski Resort
1 king bed, 1 bathroom
28 Sept – 3 Oct
4.92 out of 5 average rating, 218 reviews
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Home in Great Barrington
Stunning luxury home with pool
4 bedrooms, 4 beds, 4.5 bathrooms
9–14 Sept
4.99 out of 5 average rating, 94 reviews
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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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Home in Great Barrington
Fall Foliage @ The Barrington House: GB
5 bedrooms, 6 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 16 reviews
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Room in Great Barrington
Cozy & Convenient
1 queen bed, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 52 reviews
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Home in Sheffield
Belle Meade
2 bedrooms, 2 beds, 2 bathrooms
11–16 Nov
4.99 out of 5 average rating, 133 reviews
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Guest house in Great Barrington
Trailside Cottage
1 bedroom, 3 beds, 1 bathroom
28 Sept – 3 Oct
5.0 out of 5 average rating, 16 reviews
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Home in Great Barrington
Lovely house in the Berkshires
3 bedrooms, 4 beds, 1.5 bathrooms
7–12 Sept
4.93 out of 5 average rating, 30 reviews
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Home in Great Barrington
A Berkshires Abode - Minutes to Ski & Downtown GB!
3 bedrooms, 4 beds, 3 bathrooms
1–6 Sept
4.97 out of 5 average rating, 30 reviews
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Guest house in Great Barrington
Sweet Victorian in Housatonic
3 bedrooms, 4 beds, 1 bathroom
6–11 Sept
4.95 out of 5 average rating, 174 reviews
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Treehouse in New Marlborough
Berkshire Treehouse Retreat
3 bedrooms, 4 beds, WC
6–11 Sept
4.9 out of 5 average rating, 176 reviews
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Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.99 out of 5 average rating, 317 reviews
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Home in Great Barrington
River Cottage - Riverfront Home in Walkable Commun
3 bedrooms, 3 beds, 2 bathrooms
3–8 Sept
4.95 out of 5 average rating, 66 reviews
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Home in West Stockbridge
8 Mi to Tanglewood & Butternut Ski: Spacious Home!
6 bedrooms, 7 beds, 3.5 bathrooms
1–6 Sept
4.88 out of 5 average rating, 25 reviews
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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, 155 reviews
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Home in Great Barrington
Modern Victorian- Walk to Town
4 bedrooms, 7 beds, 2.5 bathrooms
14–19 Sept
4.97 out of 5 average rating, 142 reviews
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Cottage in Sheffield
Cheerful 3-bedroom cottage with woodstove.
3 bedrooms, 3 beds, 2.5 bathrooms
13–18 Sept
4.92 out of 5 average rating, 192 reviews