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Search results; Over 1,000 homes in Great Barrington

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Top guest favourite
Home in Great Barrington
Close to Butternut Ski with Views & Cozy Fireplace
3 bedrooms, 5 beds, 2.5 private bathrooms
26 Sept – 1 Oct
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5.0 out of 5 average rating, 39 reviews
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Top guest favourite
Home in Great Barrington
The Yellow Victorian With Chefs Kitchen
3 bedrooms, 4 beds
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
27 Sept – 2 Oct
5.0 out of 5 average rating, 56 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
Home in Great Barrington
Prime location for the best of the Berkshires
2 bedrooms, 2 queen beds
10–15 Nov
4.97 out of 5 average rating, 141 reviews
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Guest favourite
Flat in Great Barrington
King Bed | Stylish | Wi-Fi | *2m Ski Resort*
1 king bed
20–25 Sept
4.91 out of 5 average rating, 178 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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Home in Great Barrington
Mountain Views + Scenic Berkshires Hideaway
3 bedrooms, 6 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Home in Great Barrington
Never too early to book for the Holidays & NYE!
4 bedrooms, 5 beds
8–13 Oct
4.91 out of 5 average rating, 142 reviews
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Top guest favourite
Home in Great Barrington
Elegant Year-Round Lakeside Retreat with AC
4 bedrooms, 8 beds
1–6 Dec
4.96 out of 5 average rating, 193 reviews
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Top guest favourite
Home in Great Barrington
RENOVATED BERKSHIRE COUNTRY CASTLE
3 bedrooms, 3 beds
25–30 Sept
4.97 out of 5 average rating, 58 reviews
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Guest favourite
Home in Great Barrington
Great Barrington 4BR home on 3 wooded acres
4 bedrooms, 5 beds
27 Sept – 2 Oct
4.88 out of 5 average rating, 17 reviews
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Top guest favourite
Flat in Great Barrington
Walk Everywhere! | Relax in Easy Elegance!
2 bedrooms, 3 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 149 reviews
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Top guest favourite
Home in Great Barrington
Walk to Town! Great Barrington 4-bedroom farmhouse
4 bedrooms, 4 beds
26–31 Oct
5.0 out of 5 average rating, 116 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
A Berkshires Abode - Minutes to Ski & Downtown GB!
3 bedrooms, 4 beds
1–6 Oct
4.97 out of 5 average rating, 32 reviews
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Room in Great Barrington
Gracious Private Room & Bath in the Berkshires
1 queen bed
26 Sept – 1 Oct
New place to stay
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Top guest favourite
Cottage in Great Barrington
Artist Cottage
1 bedroom, 1 queen bed
5–10 Nov
4.94 out of 5 average rating, 354 reviews
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Top guest favourite
Home in Great Barrington
Country Castle-Complete privacy-minutes from town
6 bedrooms, 9 beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 68 reviews