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Search results; Over 1,000 homes in Great Barrington

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Top guest favourite
Cottage in Great Barrington
Artist Cottage
1 bedroom, 1 bed, 2 private bathrooms
8–13 Nov
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4.94 out of 5 average rating, 355 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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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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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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Guest favourite
Flat in Great Barrington
King Bed, Wi-Fi, 2m Ski Resort
1 king bed, 1 bathroom
24–29 Oct
4.94 out of 5 average rating, 204 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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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
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
Treehouse in New Marlborough
Berkshire Treehouse Retreat
3 bedrooms, 4 beds, WC
1–6 Oct
4.91 out of 5 average rating, 181 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
Guest house in Great Barrington
Trailside Cottage
1 bedroom, 3 beds, 1 bathroom
5–10 Oct
5.0 out of 5 average rating, 17 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
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
Flat in Great Barrington
The River’s Whisper
2 bedrooms, 2 queen beds, 1 bathroom
25–30 Oct
4.98 out of 5 average rating, 51 reviews
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Top guest favourite
Guest house in Stockbridge
Bitty Berkshire Bungalow
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.98 out of 5 average rating, 61 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
16–21 Oct
4.91 out of 5 average rating, 143 reviews
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Top guest favourite
Home in Egremont
Nature Retreat Near Prospect Lake
3 bedrooms, 6 beds, 1 bathroom
1–6 Nov
5.0 out of 5 average rating, 10 reviews
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Home in Great Barrington
Light-Filled Home with Pool
4 bedrooms, 4 queen beds, 3 bathrooms
11–16 Oct