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Search results; Over 1,000 homes in Canaan

Top guest favourite
Flat in Canaan
West Main
2 bedrooms, 2 beds, 1 private bathroom
14–19 Sept
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4.99 out of 5 average rating, 182 reviews
Top guest favourite
Barn in Canaan
The Cobble Barn | Fireplace • A/C • Screened Porch
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 10 reviews
Home in Canaan
Restored Berkshires Farmhouse w/ Guest House
4 bedrooms, 4 beds, 3.5 bathrooms
14–19 Sept
New place to stay
Top guest favourite
Home in Cornwall
Mountain View Getaway
3 bedrooms, 3 beds, 3 bathrooms
15–20 Sept
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Cabin in Canaan
Secret Mountain Cabin/Catskills Views/100-Acres
1 bedroom, 1 double bed, 1 bathroom
27 Sept – 2 Oct
4.96 out of 5 average rating, 47 reviews
Guest favourite
Cottage in Canaan
Historic Schoolhouse • Garden Retreat
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.9 out of 5 average rating, 59 reviews
Top guest favourite
Home in Salisbury
Under Mountain House
3 bedrooms, 3 beds, 3 bathrooms
10–15 Sept
4.98 out of 5 average rating, 182 reviews
Top guest favourite
Home in Canaan
Cozy Canaan Home near Lime Rock, Newly Renovated
4 bedrooms, 5 beds, 2 bathrooms
10–15 Sept
4.98 out of 5 average rating, 50 reviews
Guest favourite
Cabin in Cornwall
Mountain Cabin With Rustic Charm & New Fire Pit!
3 bedrooms, 3 queen beds, 1.5 bathrooms
9–14 Sept
4.85 out of 5 average rating, 82 reviews
Superhost
Cabin in Canaan
Unique, Rustic, and Beautiful
4 bedrooms, 5 beds, 2 bathrooms
8–13 Sept
4.87 out of 5 average rating, 67 reviews
Home in Canaan
Peaceful Hillside Cottage
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Canaan
Summer under the Stars
3 bedrooms, 6 beds, 2.5 bathrooms
10–15 Sept
4.97 out of 5 average rating, 35 reviews
Guest favourite
Cottage in New Marlborough
Gravel bike dream location!
2 bedrooms, 3 beds, 1 bathroom
9–14 Sept
5.0 out of 5 average rating, 63 reviews
Guest favourite
Home in Salisbury
Newly renovated charming home with chefs kitchen
3 bedrooms, 5 beds, 1.5 bathrooms
10–15 Sept
4.9 out of 5 average rating, 103 reviews
Top guest favourite
Cottage in Canaan
The Cottage at Great Falls Luxury Getaway.
2 bedrooms, 2 beds, 1 bathroom
29 Sept – 4 Oct
4.98 out of 5 average rating, 122 reviews
Guest favourite
Home in Salisbury
Lake Country Farmhouse
4 bedrooms, 5 beds, 2.5 bathrooms
19–24 Sept
4.93 out of 5 average rating, 84 reviews
Top guest favourite
Home in Canaan
A Berkshires Retreat, Stunning Views
4 bedrooms, 4 beds, 2.5 bathrooms
17–22 Sept
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Home in New Marlborough
Scenic Berkshire retreat near Great Barrington
2 bedrooms, 2 beds, 1 bathroom
9–14 Sept
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Guest suite in Falls Village
Cozy Railroad Street Retreat
1 bedroom, 1 queen bed, 1 bathroom
10–15 Sept
4.98 out of 5 average rating, 65 reviews