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Search results; Over 1,000 homes in West Stockbridge

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Guest favourite
Cottage in West Stockbridge
Historic 1810 Farmhouse - Fully Renovated
3 bedrooms, 4 beds, 2 private bathrooms
25–30 Oct
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4.94 out of 5 average rating, 155 reviews
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Guest favourite
Home in West Stockbridge
Spacious Retreat Near Tanglewood & Ski Resorts
6 bedrooms, 7 beds, 3.5 bathrooms
8–13 Nov
4.88 out of 5 average rating, 25 reviews
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Superhost
Home in West Stockbridge
Exceptional Stockbridge Retreat
3 bedrooms, 4 beds, 1.5 bathrooms
4–9 Oct
4.92 out of 5 average rating, 25 reviews
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Guest favourite
Home in West Stockbridge
Beautiful And Private Home Centrally Located
4 bedrooms, 7 beds, 3.5 bathrooms
26–31 Oct
4.96 out of 5 average rating, 67 reviews
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Top guest favourite
Home in West Stockbridge
The Filomena: Historical charm + modern design
5 bedrooms, 6 beds, 4 bathrooms
1–6 Oct
4.96 out of 5 average rating, 55 reviews
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Guest favourite
Home in West Stockbridge
Pixley Forest | 15 Mins To Tanglewood • Fireplace
4 bedrooms, 6 beds, 2 bathrooms
18–23 Oct
4.94 out of 5 average rating, 18 reviews
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Top guest favourite
Cabin in West Stockbridge
Cozy, two-bedroom cabin in a wooded glen
2 bedrooms, 2 queen beds, 1 bathroom
15–20 Nov
4.98 out of 5 average rating, 144 reviews
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Guest favourite
Room in West Stockbridge
Standard Suite with a Patio at Shaker Mill Inn
3 beds, 1 bathroom
18–23 Oct
5.0 out of 5 average rating, 11 reviews
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Guest favourite
Home in West Stockbridge
Expansive Mountainside Escape by Evergreen Home
6 bedrooms, 10 beds, 4.5 bathrooms
26–31 Oct
4.95 out of 5 average rating, 19 reviews
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Guest favourite
Home in West Stockbridge
Modern Log Cabin w/Pool & Views By Evergreen Home
4 bedrooms, 5 beds, 3.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 13 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 West Stockbridge
Secluded Chic Mountain Chalet near Tanglewood
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
4.93 out of 5 average rating, 58 reviews
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Guest favourite
Home in West Stockbridge
Rustic Modern Retreat
3 bedrooms, 3 beds, 1.5 bathrooms
1–6 Oct
4.92 out of 5 average rating, 73 reviews
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Guest favourite
Home in West Stockbridge
Crossbridge - Vintage Charm & Unique Character
6 bedrooms, 6 beds, 7 bathrooms
26–31 Oct
5.0 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, 1 bathroom
18–23 Oct
4.95 out of 5 average rating, 177 reviews
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Guest favourite
Home in Stockbridge
Light Filled - Modern Rustic Home
4 bedrooms, 5 beds, 2.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 6 reviews
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Guest favourite
Cabin in West Stockbridge
Serene rustic mountain cabin in the Berkshires!
1 bedroom, 2 beds, 1 bathroom
1–6 Oct
4.88 out of 5 average rating, 17 reviews
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Top guest favourite
Home in West Stockbridge
Berkshires-Enjoy The Peak, private home
3 bedrooms, 3 beds, 2.5 bathrooms
30 Oct – 4 Nov
4.95 out of 5 average rating, 111 reviews
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Guest favourite
Room in West Stockbridge
Deluxe Suite with a Balcony Pets allowed
1 queen bed, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 7 reviews