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Search results; Over 1,000 homes in Great Barrington

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Guest favourite
Chalet in Great Barrington
Berkshire "Zen" Cottage
3 bedrooms, 4 beds, 2 private bathrooms
4–9 Oct
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4.94 out of 5 average rating, 89 reviews
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Guest favourite
Flat in Great Barrington
King Bed |Wi-Fi| 2m to Ski Resort
1 king bed, 1 bathroom
4–9 Oct
4.92 out of 5 average rating, 224 reviews
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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, 161 reviews
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Home in Great Barrington
Riverside Retreat in the Berkshires
3 bedrooms, 4 beds, 1 bathroom
25–30 Oct
4.63 out of 5 average rating, 40 reviews
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Guest favourite
Flat in Great Barrington
King Bed | Patio | 2m to Ski Resort
1 king bed, 1 bathroom
1–6 Oct
4.91 out of 5 average rating, 187 reviews
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Guest favourite
Guest house in Great Barrington
Sweet Victorian in Housatonic
3 bedrooms, 4 beds, 1 bathroom
18–23 Oct
4.95 out of 5 average rating, 177 reviews
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Top guest favourite
Home in Great Barrington
A Berkshires Abode - Minutes to Ski & Downtown GB!
3 bedrooms, 4 beds, 3 bathrooms
1–6 Oct
4.97 out of 5 average rating, 33 reviews
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Top guest favourite
Home in Great Barrington
Berkshires Black Abbey
3 bedrooms, 4 beds, 3 bathrooms
4–9 Oct
5.0 out of 5 average rating, 47 reviews
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Superhost
Home in Sheffield
Timber Frame • Big Deck • Game Room | Near Trails
4 bedrooms, 6 beds, 4 bathrooms
4–9 Oct
New place to stay
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Guest favourite
Home in Great Barrington
GB at your doorstep
3 bedrooms, 4 beds, 2 bathrooms
26–31 Oct
4.94 out of 5 average rating, 141 reviews
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Guest favourite
Home in Great Barrington
Sunsets On Blue Hill, Newly Renovated Farmhouse
4 bedrooms, 6 beds, 3 bathrooms
4–9 Oct
4.94 out of 5 average rating, 84 reviews
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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
Modern Victorian- Walk to Town
4 bedrooms, 7 beds, 2.5 bathrooms
18–23 Oct
4.97 out of 5 average rating, 142 reviews
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Guest favourite
Flat in Great Barrington
Kitchenette|King Bed|Couch
1 bedroom, 1 king bed, 1 bathroom
18–23 Oct
4.89 out of 5 average rating, 191 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
30 Oct – 4 Nov
5.0 out of 5 average rating, 56 reviews
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Top guest favourite
Home in Great Barrington
Higgins House
3 bedrooms, 3 queen beds, 2.5 bathrooms
19–24 Oct
5.0 out of 5 average rating, 6 reviews
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Room in Great Barrington
Gracious Private Room & Bath in the Berkshires
1 queen bed, 1.5 bathrooms
15–20 Oct
New place to stay
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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
16–21 Oct
4.91 out of 5 average rating, 143 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
7–12 Dec
5.0 out of 5 average rating, 60 reviews