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Search results; Over 1,000 homes in Berkshire

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Guest favourite
Home in Berkshire, Vermont, US
1860 Farmhouse
6 bedrooms, 8 beds, 2.5 private bathrooms
20–25 Oct
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4.94 out of 5 average rating, 169 reviews
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Top guest favourite
Cabin in Berkshire, Vermont, US
Rustic Log Cabin in Berkshire, Vermont
3 bedrooms, 4 beds, 1.5 bathrooms
16–21 Sept
4.99 out of 5 average rating, 103 reviews
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Top guest favourite
Home in Berkshire, Vermont, US
The Farmhouse
4 bedrooms, 6 beds, 2 bathrooms
16–21 Sept
5.0 out of 5 average rating, 33 reviews
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Top guest favourite
Cabin in Richford, Vermont, US
Cozy Cabin in a Cabin • Near Jay Peak Ski Resort
4 bedrooms, 5 beds, 2.5 bathrooms
16–21 Sept
5.0 out of 5 average rating, 24 reviews
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Top guest favourite
Home in Richford, Vermont, US
Peaceful + Cozy Farmhouse Near Jay Peak + Sutton
2 bedrooms, 3 beds, 1 bathroom
21–26 Sept
4.99 out of 5 average rating, 163 reviews
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Guest favourite
Home in Berkshire, Vermont, US
Quiet Vermont Getaway w/ Stunning Views
4 bedrooms, 4 beds, 2.5 bathrooms
17–22 Sept
5.0 out of 5 average rating, 7 reviews
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Guest favourite
Home in Berkshire, Vermont, US
Cape Hollow House - Beautiful summer location
3 bedrooms, 5 beds, 1 bathroom
18–23 Sept
4.84 out of 5 average rating, 49 reviews
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Superhost
Home in Richford, Vermont, US
Book now for fall foliage. Skiing is coming.
7 bedrooms, 9 beds, 5.5 bathrooms
27 Sept – 2 Oct
4.8 out of 5 average rating, 20 reviews
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Top guest favourite
Farm stay in Berkshire, Vermont, US
The Berkshire House - Spacious Farmhouse
7 bedrooms, 9 beds, 4 bathrooms
20–25 Oct
4.98 out of 5 average rating, 61 reviews
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Superhost
Guest suite in Richford, Vermont, US
Ski Jay Peak and Mt. Sutton from Cozy Farmhouse
3 bedrooms, 4 beds, 1 bathroom
1–6 Nov
New place to stay
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Top guest favourite
Flat in Richford, Vermont, US
Northern Vermont shackteau
2 bedrooms, 2 beds, 1 bathroom
17–22 Sept
4.95 out of 5 average rating, 164 reviews
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Flat in Frelighsburg, Quebec, Canada
La Sittelle
1 bedroom, 2 beds, 1 bathroom
16–21 Sept
New place to stay
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Top guest favourite
Home in Berkshire, Vermont, US
Cozy Vermont Home Near Jay Peak & Wedding Venues
3 bedrooms, 4 beds, 2 bathrooms
20–25 Oct
4.96 out of 5 average rating, 24 reviews
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Top guest favourite
Cabin in Richford, Vermont, US
Scandi Cabin • Expansive Valley & Green Mtn Views
1 bedroom, 1 king bed, 1 bathroom
26 Sept – 1 Oct
5.0 out of 5 average rating, 19 reviews
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Guest favourite
Farm stay in Sheldon, Vermont, US
VT farmhouse- new gameroom and rail trail access
4 bedrooms, 4 beds, 1.5 bathrooms
17–22 Sept
4.72 out of 5 average rating, 43 reviews
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Guest favourite
Home in Dunham, Canada
Cozy home, Lake 2 min walk 2 kayaks available
4 bedrooms, 5 beds, 1 bathroom
27 Sept – 2 Oct
4.93 out of 5 average rating, 44 reviews
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Guest favourite
Farm stay in Richford, Vermont, US
Hi Vue Cabin
1 bedroom, 3 beds, 1 bathroom
16–21 Sept
4.75 out of 5 average rating, 89 reviews
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Guest favourite
Home in Franklin, Vermont, US
Birch and Maples
3 bedrooms, 5 beds, 2 bathrooms
18–23 Sept
5.0 out of 5 average rating, 6 reviews
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Guest favourite
Flat in Frelighsburg, Quebec, Canada
Apartment in the heart of the village
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
4.73 out of 5 average rating, 30 reviews