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Search results; Over 1,000 homes in Great Barrington

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Guest favourite
Holiday home in Great Barrington
Home in Great Barrington. Steps from downtown!
2 bedrooms, 3 beds, 1 private bathroom
25–30 Oct
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4.94 out of 5 average rating, 295 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
Photo 1 of 29
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
Prime location for the best of the Berkshires
2 bedrooms, 2 queen beds, 1 bathroom
10–15 Nov
4.97 out of 5 average rating, 141 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
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
Home in Great Barrington
Walt's Townhouse - Berkshire living at its best
3 bedrooms, 3 beds, 2 bathrooms
29 Oct – 3 Nov
5.0 out of 5 average rating, 86 reviews
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Guest favourite
Flat in Great Barrington
King Bed | Stylish | Wi-Fi | *2m Ski Resort*
1 king bed, 1 bathroom
20–25 Sept
4.91 out of 5 average rating, 178 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
Flat in Great Barrington
Walk Everywhere! | Relax in Easy Elegance!
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 149 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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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
Photo 1 of 29
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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Guest favourite
Home in Great Barrington
Never too early to book for the Holidays & NYE!
4 bedrooms, 5 beds, 2 bathrooms
8–13 Oct
4.91 out of 5 average rating, 142 reviews
Photo 1 of 29
Top guest favourite
Barn in New Marlborough
Hartsville Barn in the Berkshires
2 bedrooms, 2 king beds, 1 bathroom
20–25 Oct
4.98 out of 5 average rating, 51 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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Top guest favourite
Home in Great Barrington
Berkshire Bliss: Nature + Luxe
5 bedrooms, 7 beds, 4.5 bathrooms
14–19 Oct
5.0 out of 5 average rating, 12 reviews
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Top guest favourite
Home in Great Barrington
Berkshires Black Abbey
3 bedrooms, 4 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 47 reviews
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Guest favourite
Home in Great Barrington
Great Barrington 4BR home on 3 wooded acres
4 bedrooms, 5 beds, 3.5 bathrooms
27 Sept – 2 Oct
4.88 out of 5 average rating, 17 reviews