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Search results; Over 1,000 homes in Great Barrington

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Guest favourite
Chalet in Great Barrington
Berkshire "Zen" Cottage
3 bedrooms, 4 beds, 2 private bathrooms
17–22 Sept
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4.94 out of 5 average rating, 88 reviews
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Top guest favourite
Flat in Great Barrington
King Bed | Patio | 2m to Ski Resort
1 king bed, 1 bathroom
20–25 Sept
4.92 out of 5 average rating, 183 reviews
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Top guest favourite
Loft in Great Barrington
The Old Red Barn
1 bedroom, 1 queen bed, 1 bathroom
26 Sept – 1 Oct
4.99 out of 5 average rating, 370 reviews
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Home in Great Barrington
Luxurious Victorian, Walking Distance to Town
4 bedrooms, 4.5 bathrooms
19–24 Sept
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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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Top guest favourite
Guest house in Great Barrington
Trailside Cottage
1 bedroom, 3 beds, 1 bathroom
29 Oct – 3 Nov
5.0 out of 5 average rating, 17 reviews
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Top guest favourite
Barn in New Marlborough
Hartsville Barn in the Berkshires
2 bedrooms, 2 king beds, 1 bathroom
27 Oct – 1 Nov
4.98 out of 5 average rating, 50 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
16–21 Sept
4.88 out of 5 average rating, 24 reviews
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Guest favourite
Home in Great Barrington
River Cottage - Riverfront Home in Walkable Commun
3 bedrooms, 3 beds, 2 bathrooms
18–23 Sept
4.96 out of 5 average rating, 69 reviews
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Top guest favourite
Flat in Great Barrington
Zen River Studio
1 bedroom, 1 king bed, 1 bathroom
20–25 Oct
4.93 out of 5 average rating, 43 reviews
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Home in Great Barrington
Mountain Views + Scenic Berkshires Hideaway
3 bedrooms, 6 beds, 2 bathrooms
16–21 Sept
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Top guest favourite
Home in Monterey
Berkshires Retreat | Fall Foliage | Fenced Yard
5 bedrooms, 7 beds, 3.5 bathrooms
16–21 Sept
5.0 out of 5 average rating, 49 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
16–21 Sept
4.98 out of 5 average rating, 50 reviews
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Top guest favourite
Flat in Great Barrington
The River’s Whisper
2 bedrooms, 2 queen beds, 1 bathroom
28 Sept – 3 Oct
4.98 out of 5 average rating, 51 reviews
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Guest favourite
Home in Great Barrington
Waterfront Modern Lake Mansfield Retreat
3 bedrooms, 3 beds, 2.5 bathrooms
17–22 Sept
4.96 out of 5 average rating, 80 reviews
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Guest favourite
Cabin in Great Barrington
Kenyon's Cabin
2 bedrooms, 4 beds, 1 bathroom
16–21 Sept
4.87 out of 5 average rating, 38 reviews
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Guest favourite
Holiday home in Great Barrington
Home in Great Barrington. Steps from downtown!
2 bedrooms, 3 beds, 1 bathroom
25–30 Oct
4.94 out of 5 average rating, 294 reviews
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Guest favourite
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms, 4 beds, 2 bathrooms
16–21 Sept
4.9 out of 5 average rating, 10 reviews
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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, 222 reviews