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Search results; Over 1,000 homes in Great Barrington

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Guest favourite
Home in Great Barrington
Great Barrington Lakeside Getaway w/ Kayak & Grill
4 bedrooms, 6 beds, 4 private bathrooms
2–7 Nov
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4.84 out of 5 average rating, 43 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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Home in Great Barrington
Mountain Views + Scenic Berkshires Hideaway
3 bedrooms, 6 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Great Barrington
RENOVATED BERKSHIRE COUNTRY CASTLE
3 bedrooms, 3 beds, 3 bathrooms
12–17 Oct
4.97 out of 5 average rating, 58 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
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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Superhost
Home in Great Barrington
Prime Location, Recently Redesigned, Riverfront!
4 bedrooms, 6 beds, 2 bathrooms
1–6 Oct
4.9 out of 5 average rating, 10 reviews
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Top guest favourite
Home in Great Barrington
Country Castle-Complete privacy-minutes from town
6 bedrooms, 9 beds, 3 bathrooms
4–9 Oct
4.97 out of 5 average rating, 69 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
Cottage in Monterey
Beaver Lodge
3 bedrooms, 3 queen beds, 1.5 bathrooms
24–29 Oct
5.0 out of 5 average rating, 84 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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Guest favourite
Home in Great Barrington
Hilltop Ski and Sun Chalet with Hot Tub
5 bedrooms, 6 beds, 3.5 bathrooms
4–9 Oct
4.97 out of 5 average rating, 63 reviews
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Guest favourite
Cabin in Great Barrington
Kenyon's Cabin
2 bedrooms, 4 beds, 1 bathroom
1–6 Oct
4.87 out of 5 average rating, 38 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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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, 186 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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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
Home in Great Barrington
Charming, view, large deck, private/walk downtown
3 bedrooms, 4 beds, 2.5 bathrooms
17–22 Oct
4.89 out of 5 average rating, 102 reviews
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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