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Search results; Over 1,000 homes in Great Barrington

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Top guest favourite
Home in Great Barrington
Waterfront Modern Lake Mansfield Retreat
3 bedrooms, 3 beds, 2.5 private bathrooms
14–19 Sept
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4.97 out of 5 average rating, 78 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
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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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
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.9 out of 5 average rating, 10 reviews
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Guest favourite
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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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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Top guest favourite
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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Top guest favourite
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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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
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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
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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
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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Guest favourite
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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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, 154 reviews
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Superhost
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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Top guest favourite
Home in Great Barrington
Beautiful House in the Woods: Huge Yard, Hot Tub
4 bedrooms, 5 beds, 3.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 24 reviews
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Top guest favourite
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, 316 reviews