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Search results; Over 1,000 homes in Great Barrington

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Top guest favourite
Loft in Great Barrington
The Old Red Barn
1 bedroom, 1 bed, 1 private bathroom
26–31 Oct
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4.99 out of 5 average rating, 371 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, 184 reviews
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Top guest favourite
Home in Great Barrington
Stunning luxury home with pool
4 bedrooms, 4 beds, 4.5 bathrooms
19–24 Oct
4.99 out of 5 average rating, 95 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
20–25 Sept
5.0 out of 5 average rating, 59 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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Guest favourite
Flat in Great Barrington
Berkshire Retreat|King Bed|Wi-Fi|2m Ski Resort
1 king bed, 1 bathroom
27 Sept – 2 Oct
4.89 out of 5 average rating, 189 reviews
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Home in Great Barrington
Luxurious Victorian, Walking Distance to Town
4 bedrooms, 4.5 bathrooms
23–28 Sept
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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, 160 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
20–25 Sept
5.0 out of 5 average rating, 26 reviews
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Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
3 bedrooms, 4 beds, 1 bathroom
27 Sept – 2 Oct
4.95 out of 5 average rating, 176 reviews
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Top guest favourite
Home in Great Barrington
Walk to Town! Great Barrington 4-bedroom farmhouse
4 bedrooms, 4 beds, 2 bathrooms
26–31 Oct
5.0 out of 5 average rating, 116 reviews
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Guest favourite
Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms, 4 beds, 2 bathrooms
19–24 Oct
4.9 out of 5 average rating, 10 reviews
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Top guest favourite
Home in Great Barrington
Elegant Year-Round Lakeside Retreat with AC
4 bedrooms, 8 beds, 3 bathrooms
1–6 Dec
4.96 out of 5 average rating, 193 reviews
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Room in Great Barrington
Gracious Private Room & Bath in the Berkshires
1 queen bed, 1.5 bathrooms
26 Sept – 1 Oct
New place to stay
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Top guest favourite
Cottage in Great Barrington
Cottage on Scenic Road
1 bedroom, 1 queen bed, 1 bathroom
28 Sept – 3 Oct
4.91 out of 5 average rating, 281 reviews
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Guest favourite
Home in Great Barrington
Hilltop Ski and Sun Chalet with Hot Tub
5 bedrooms, 6 beds, 3.5 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 63 reviews
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Guest favourite
Cottage in Great Barrington
The Cottage at The Barrington House
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.93 out of 5 average rating, 224 reviews
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Guest favourite
Home in Great Barrington
Cottage by the Lake | Fall Hiking, Skiing & More
2 bedrooms, 4 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Home in Great Barrington
RENOVATED BERKSHIRE COUNTRY CASTLE
3 bedrooms, 3 beds, 3 bathrooms
25–30 Sept
4.97 out of 5 average rating, 58 reviews