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Search results; Over 1,000 homes in Great Barrington

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Top guest favourite
Home in Great Barrington
Sauna + Hot Tub Escape | Private & Pet Friendly
3 bedrooms, 4 beds, 2 private bathrooms
27 Sept – 2 Oct
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5.0 out of 5 average rating, 56 reviews
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Top guest favourite
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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Guest favourite
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, 173 reviews
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Guest favourite
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 favourite
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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Top guest favourite
Home in Great Barrington
The Yellow Victorian With Chefs Kitchen
3 bedrooms, 4 beds, 3.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 59 reviews
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Home in Great Barrington
Woodland - Stunning 5 bedroom home in GB!
5 bedrooms, 10 beds, 3 bathrooms
27 Sept – 2 Oct
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Home in Great Barrington
Garden Retreat, 1st fl KING ste, EV, close to all
3 bedrooms, 4 beds, 3 bathrooms
1–6 Sept
5.0 out of 5 average rating, 4 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
9–14 Sept
4.97 out of 5 average rating, 138 reviews
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Guest favourite
Home in Great Barrington
Charming, view, large deck, private/walk downtown
3 bedrooms, 4 beds, 2.5 bathrooms
6–11 Sept
4.89 out of 5 average rating, 99 reviews
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Guest favourite
Home in Great Barrington
Berkshire’s Best-hottub-fitness/gameroom
4 bedrooms, 4 beds, 2 bathrooms
6–11 Sept
4.92 out of 5 average rating, 24 reviews
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Guest favourite
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
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Top guest favourite
Flat in Great Barrington
King Bed | Stylish | Wi-Fi | *2m Ski Resort*
1 king bed, 1 bathroom
7–12 Sept
4.92 out of 5 average rating, 171 reviews
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Guest favourite
Flat in Great Barrington
King Bed |Wi-Fi| 2m to Ski Resort
1 king bed, 1 bathroom
6–11 Sept
4.92 out of 5 average rating, 217 reviews
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Top guest favourite
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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Top guest favourite
Home in Monterey
Berkshires Retreat | Fall Foliage | Fenced Yard
5 bedrooms, 7 beds, 3.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 49 reviews
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Cottage in Sheffield
Charming Handcrafted Cottage in the Berkshires!
3 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
4.78 out of 5 average rating, 101 reviews
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Top guest favourite
Cottage in Great Barrington
Artist Cottage
1 bedroom, 1 queen bed, 2 bathrooms
1–6 Dec
4.93 out of 5 average rating, 352 reviews
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Top guest favourite
Barn in New Marlborough
Hartsville Barn in the Berkshires
2 bedrooms, 2 king beds, 1 bathroom
16–21 Nov
4.98 out of 5 average rating, 47 reviews