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Search results; Over 1,000 homes in Berkshire

Top guest favourite
Cabin in Berkshire, Vermont, US
Rustic Log Cabin in Berkshire, Vermont
3 bedrooms, 4 beds, 1.5 private bathrooms
12–17 Sept
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4.99 out of 5 average rating, 102 reviews
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
10–15 Sept
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Home in Richford, Vermont, US
Peaceful + Cozy Farmhouse Near Jay Peak + Sutton
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 162 reviews
Top guest favourite
Home in Berkshire, Vermont, US
The Farmhouse
4 bedrooms, 6 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 32 reviews
Guest favourite
Home in Berkshire, Vermont, US
1860 Farmhouse
6 bedrooms, 8 beds, 2.5 bathrooms
10–15 Sept
4.94 out of 5 average rating, 169 reviews
Guest favourite
Home in Berkshire, Vermont, US
Cape Hollow House - Beautiful summer location
3 bedrooms, 5 beds, 1 bathroom
10–15 Sept
4.84 out of 5 average rating, 49 reviews
Top guest favourite
Home in Abercorn, Canada
Modern, clean, natural light filled chalet
2 bedrooms, 2 beds, 2 bathrooms
12–17 Oct
4.99 out of 5 average rating, 77 reviews
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
Guest favourite
Chalet in Frelighsburg, Quebec, Canada
Frelighsburg-en-haut
3 bedrooms, 5 beds, 1.5 bathrooms
10–15 Sept
4.91 out of 5 average rating, 11 reviews
Top guest favourite
Home in Berkshire, Vermont, US
Cozy Vermont Home Near Jay Peak & Wedding Venues
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.96 out of 5 average rating, 24 reviews
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
Guest favourite
Chalet in Dunham, Canada
Quiet cabin- wine route/waterfront/ mountain views
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
4.92 out of 5 average rating, 100 reviews
Superhost
Home in Richford, Vermont, US
Cozy Farmhouse - 5 Star Views - Jay Peak - Groups
4 bedrooms, 5 beds, 2 bathrooms
16–21 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Cabin in Richford, Vermont, US
JaMari Acres Jay Peak
3 bedrooms, 6 beds, 2 bathrooms
10–15 Sept
4.94 out of 5 average rating, 17 reviews
Top guest favourite
Home in Enosburg, Vermont, US
The Gambrel Mountain Retreat at Twin Ponds
2 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 70 reviews
Superhost
Home in Frelighsburg, Quebec, Canada
Spa, Nature & Mountain | Le Pinacle
2 bedrooms, 3 beds, 1.5 bathrooms
18–23 Oct
5.0 out of 5 average rating, 3 reviews
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
Top guest favourite
Cabin in Enosburg, Vermont, US
The Rustic Retreat at Twin Ponds
2 bedrooms, 3 beds, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 209 reviews
Top guest favourite
Home in Montgomery, Vermont, US
Pet Welcoming Cottage l Hiking + Fishing + Golf
3 bedrooms, 4 beds, 2 bathrooms
10–15 Sept
5.0 out of 5 average rating, 15 reviews