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Search results; Over 1,000 homes in Great Barrington

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Guest favourite
Holiday home in Great Barrington
Home in Great Barrington. Steps from downtown!
2 bedrooms, 3 beds, 1 private bathroom
25–30 Oct
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4.94 out of 5 average rating, 295 reviews
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Room in Great Barrington
Gracious Private Room & Bath in the Berkshires
1 queen bed, 1.5 bathrooms
15–20 Oct
New place to stay
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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, 223 reviews
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Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
3 bedrooms, 4 beds, 1 bathroom
18–23 Oct
4.95 out of 5 average rating, 177 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
Home in Great Barrington
Seekonk Hill
2 bedrooms, 2 queen beds, 2 bathrooms
26–31 Oct
4.98 out of 5 average rating, 48 reviews
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Hotel room in Lee
Endless Family Fun: Pools, Arcade Room & Mini Golf
2 bedrooms, 2 bathrooms
1–6 Oct
4.66 out of 5 average rating, 35 reviews
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Home in Great Barrington
Mountain Views + Scenic Berkshires Hideaway
3 bedrooms, 6 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 3 reviews
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Superhost
Home in Great Barrington
Prime Location, Recently Redesigned, Riverfront!
4 bedrooms, 6 beds, 2 bathrooms
1–6 Oct
4.9 out of 5 average rating, 10 reviews
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Top guest favourite
Barn in New Marlborough
Hartsville Barn in the Berkshires
2 bedrooms, 2 king beds, 1 bathroom
20–25 Oct
4.98 out of 5 average rating, 51 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
30 Oct – 4 Nov
5.0 out of 5 average rating, 56 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, 143 reviews
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Guest favourite
Home in Great Barrington
Berkshires Family Oasis with Hot Tub, Patio, Gym
4 bedrooms, 7 beds, 2.5 bathrooms
11–16 Oct
4.98 out of 5 average rating, 50 reviews
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Top guest favourite
Cottage in Great Barrington
Artist Cottage
1 bedroom, 1 queen bed, 2 bathrooms
5–10 Nov
4.94 out of 5 average rating, 354 reviews
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Superhost
Home in Great Barrington
Pristine 3 Bedroom, Walk-to Gt Barrington Center!
3 bedrooms, 4 beds, 1.5 bathrooms
1–6 Oct
4.88 out of 5 average rating, 25 reviews
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Guest favourite
Home in West Stockbridge
Spacious Retreat near Tanglewood & Ski Resorts
6 bedrooms, 7 beds, 3.5 bathrooms
8–13 Nov
4.88 out of 5 average rating, 25 reviews
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Top guest favourite
Cottage in Monterey
Beaver Lodge
3 bedrooms, 3 queen beds, 1.5 bathrooms
14–19 Oct
5.0 out of 5 average rating, 83 reviews
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Guest favourite
Cottage in Sheffield
Cheerful 3-bedroom cottage with woodstove.
3 bedrooms, 3 beds, 2.5 bathrooms
24–29 Oct
4.92 out of 5 average rating, 195 reviews
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Guest favourite
Home in Great Barrington
Berkshires Retreat!
5 bedrooms, 9 beds, 2.5 bathrooms
25–30 Oct
4.95 out of 5 average rating, 41 reviews