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Search results; Over 1,000 homes in Great Barrington

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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 private bathrooms
20–25 Sept
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5.0 out of 5 average rating, 26 reviews
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Top guest favourite
Home in Great Barrington
The Yellow Victorian With Chefs Kitchen
3 bedrooms, 4 beds
18–23 Sept
5.0 out of 5 average rating, 59 reviews
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Top guest favourite
Flat in Great Barrington
King Bed | Patio | 2m to Ski Resort
1 king bed
20–25 Sept
4.92 out of 5 average rating, 183 reviews
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Top guest favourite
Home in Great Barrington
Stunning luxury home with pool
4 bedrooms, 4 beds
19–24 Oct
4.99 out of 5 average rating, 95 reviews
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Top guest favourite
Home in Great Barrington
Sauna + Hot Tub Escape | Private & Pet Friendly
3 bedrooms, 4 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 56 reviews
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Guest favourite
Home in Great Barrington
Spacious and Rustic retreat in the Berkshires
4 bedrooms, 6 beds
16–21 Apr
5.0 out of 5 average rating, 7 reviews
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Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
3 bedrooms, 4 beds
27 Sept – 2 Oct
4.95 out of 5 average rating, 176 reviews
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Top guest favourite
Cottage in Monterey
Beaver Lodge
3 bedrooms, 3 queen beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 83 reviews
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Top guest favourite
Home in Great Barrington
Seekonk Hill
2 bedrooms, 2 queen beds
26–31 Oct
4.98 out of 5 average rating, 48 reviews
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Top guest favourite
Flat in Great Barrington
Walk Everywhere! | Relax in Easy Elegance!
2 bedrooms, 3 beds
18–23 Sept
5.0 out of 5 average rating, 149 reviews
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Top guest favourite
Home in Great Barrington
Berkshires Black Abbey
3 bedrooms, 4 beds
20–25 Sept
5.0 out of 5 average rating, 47 reviews
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Guest favourite
Home in Great Barrington
Hilltop Ski and Sun Chalet with Hot Tub
5 bedrooms, 6 beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 63 reviews
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Top guest favourite
Home in Great Barrington
Walt's Townhouse - Berkshire living at its best
3 bedrooms, 3 beds
29 Oct – 3 Nov
5.0 out of 5 average rating, 86 reviews
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Guest favourite
Cottage in Sheffield
Cheerful 3-bedroom cottage with woodstove.
3 bedrooms, 3 beds
20–25 Sept
4.92 out of 5 average rating, 195 reviews
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Top guest favourite
Cottage in Great Barrington
Cottage on Scenic Road
1 bedroom, 1 queen bed
28 Sept – 3 Oct
4.91 out of 5 average rating, 281 reviews
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Guest favourite
Chalet in Great Barrington
Berkshire "Zen" Cottage
3 bedrooms, 4 beds
19–24 Sept
4.94 out of 5 average rating, 88 reviews
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Guest favourite
Flat in Great Barrington
King Bed |Wi-Fi| 2m to Ski Resort
1 king bed
4–9 Oct
4.92 out of 5 average rating, 222 reviews
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Home in Great Barrington
Full Moon Farm
3 bedrooms, 3 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Home in Great Barrington
River Cottage - Riverfront Home in Walkable Commun
3 bedrooms, 3 beds
18–23 Sept
4.96 out of 5 average rating, 69 reviews