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Search results; Over 1,000 homes in Berkshire

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Top guest favourite
Cabin in Berkshire, Vermont, US
Rustic Log Cabin in Berkshire, Vermont
3 bedrooms, 4 beds, 1.5 private bathrooms
11–16 Oct
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4.99 out of 5 average rating, 103 reviews
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Guest favourite
Home in Berkshire, Vermont, US
1860 Farmhouse
6 bedrooms, 8 beds, 2.5 bathrooms
20–25 Oct
4.94 out of 5 average rating, 170 reviews
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Guest favourite
Home in Berkshire, Vermont, US
Cape Hollow House - Fall foliage at its best
3 bedrooms, 5 beds, 1 bathroom
4–9 Oct
4.84 out of 5 average rating, 49 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
12–17 Oct
5.0 out of 5 average rating, 24 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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Top guest favourite
Home in Berkshire, Vermont, US
The Farmhouse
4 bedrooms, 6 beds, 2 bathrooms
5–10 Oct
5.0 out of 5 average rating, 33 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
13–18 Oct
4.99 out of 5 average rating, 165 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
23–28 Oct
5.0 out of 5 average rating, 7 reviews
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Superhost
Home in Richford, Vermont, US
Cozy Farmhouse - 5 Star Views - Jay Peak - Groups
4 bedrooms, 5 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Flat in Richford, Vermont, US
Northern Vermont shackteau
2 bedrooms, 2 beds, 1 bathroom
13–18 Oct
4.95 out of 5 average rating, 164 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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Home in Jay, Vermont, US
3 Bedroom Mountain View Ranch 10 min to Jay Peak
3 bedrooms, 4 beds, 2 bathrooms
1–6 Oct
New place to stay
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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
24–29 Oct
4.8 out of 5 average rating, 20 reviews
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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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Hotel in Richford, Vermont, US
Cozy & Convenient Richford, VT (Room 14)
1 bedroom, 1 queen bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 4 reviews
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Guest favourite
Home in Montgomery, Vermont, US
Private 3BR, 1.5 Bath — Green Mountain Guesthouse
3 bedrooms, 5 beds, 1.5 bathrooms
4–9 Oct
4.94 out of 5 average rating, 16 reviews
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Guest favourite
Home in Fairfield, Vermont, US
Sugar House Homestead: A Perfect Retreat
3 bedrooms, 5 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 12 reviews
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Hotel in Richford, Vermont, US
Cozy & Convenient Richford, VT (Room 16)
1 bedroom, 3 double beds, 1 bathroom
4–9 Oct
New place to stay
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Flat in Frelighsburg, Quebec, Canada
The Hummingbird
1 bedroom, 2 beds, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 4 reviews