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Search results; Over 1,000 homes in Great Barrington

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Top guest favourite
Home in Great Barrington
Seekonk Hill
2 bedrooms, 2 beds, 2 private bathrooms
26–31 Oct
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4.98 out of 5 average rating, 48 reviews
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Top guest favourite
Home in Great Barrington
Sauna + Hot Tub Escape | Private & Pet Friendly
3 bedrooms, 4 beds
30 Oct – 4 Nov
5.0 out of 5 average rating, 56 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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Home in Great Barrington
Downtown Housatonic house –10 miles to Tangelwood
3 bedrooms, 4 beds
19–24 Oct
4.9 out of 5 average rating, 10 reviews
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Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
3 bedrooms, 4 beds
18–23 Oct
4.95 out of 5 average rating, 177 reviews
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Home in Great Barrington
Mountain Views + Scenic Berkshires Hideaway
3 bedrooms, 6 beds
1–6 Oct
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Home in Great Barrington
Charming, view, large deck, private/walk downtown
3 bedrooms, 4 beds
17–22 Oct
4.89 out of 5 average rating, 102 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, 223 reviews
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Superhost
Home in Great Barrington
Woodland - Stunning 5 bedroom home in GB!
5 bedrooms, 10 beds
1–6 Oct
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Superhost
Home in Great Barrington
Prime Location, Recently Redesigned, Riverfront!
4 bedrooms, 6 beds
1–6 Oct
4.9 out of 5 average rating, 10 reviews
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Top guest favourite
Home in Great Barrington
Berkshire Bliss: Nature + Luxe
5 bedrooms, 7 beds
14–19 Oct
5.0 out of 5 average rating, 12 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
Flat in Great Barrington
King Bed, Wi-Fi, 2m Ski Resort
1 king bed
24–29 Oct
4.94 out of 5 average rating, 204 reviews
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Top guest favourite
Cottage in Monterey
Beaver Lodge
3 bedrooms, 3 queen beds
14–19 Oct
5.0 out of 5 average rating, 84 reviews
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Room in Great Barrington
Gracious Private Room & Bath in the Berkshires
1 queen bed
15–20 Oct
New place to stay
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Home in Great Barrington
Riverside Retreat in the Berkshires
3 bedrooms, 4 beds
25–30 Oct
4.61 out of 5 average rating, 38 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
Cabin in Great Barrington
Kenyon's Cabin
2 bedrooms, 4 beds
1–6 Oct
4.87 out of 5 average rating, 38 reviews
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Top guest favourite
Barn in New Marlborough
Hartsville Barn in the Berkshires
2 bedrooms, 2 king beds
20–25 Oct
4.98 out of 5 average rating, 51 reviews