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Search results; Over 1,000 homes in Canaan

Guest favourite
Tent in Canaan
glamping tent in hidden pasture
3 beds, 0.5 private bathroom
15–20 Sept
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4.97 out of 5 average rating, 35 reviews
Top guest favourite
Barn in Canaan
The Cobble Barn | Fireplace • A/C • Screened Porch
2 bedrooms, 3 beds, 1 bathroom
18–23 Oct
5.0 out of 5 average rating, 11 reviews
Home in Canaan
Restored Berkshires Farmhouse w/ Guest House
4 bedrooms, 4 beds, 3.5 bathrooms
15–20 Sept
New place to stay
Home in Canaan
Peaceful Hillside Cottage
3 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
Cabin in Canaan
Unique, Rustic, and Beautiful
4 bedrooms, 5 beds, 2 bathrooms
19–24 Sept
4.87 out of 5 average rating, 67 reviews
Top guest favourite
Home in Canaan
Cozy Canaan Home near Lime Rock, Newly Renovated
4 bedrooms, 5 beds, 2 bathrooms
28 Sept – 3 Oct
4.98 out of 5 average rating, 52 reviews
Guest favourite
Cottage in Canaan
Historic Schoolhouse • Garden Retreat
2 bedrooms, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.9 out of 5 average rating, 60 reviews
Guest favourite
Cottage in Canaan
Cozy Little Cottage
3 bedrooms, 4 beds, 2 bathrooms
29 Sept – 4 Oct
4.84 out of 5 average rating, 202 reviews
Top guest favourite
Flat in Canaan
West Main
2 bedrooms, 2 queen beds, 1 bathroom
25–30 Oct
4.99 out of 5 average rating, 182 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, 49 reviews
Top guest favourite
Home in Canaan
Luxury/pool/private Villa Mariana Blackberry River
4 bedrooms, 6 beds, 3.5 bathrooms
15–20 Sept
5.0 out of 5 average rating, 35 reviews
Guest favourite
Home in Salisbury
Cleaveland
3 bedrooms, 3 beds, 1.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 24 reviews
Guest favourite
Home in Canaan
Spacious house located near many attractions!
2 bedrooms, 3 beds, 2 bathrooms
18–23 Sept
5.0 out of 5 average rating, 12 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, 123 reviews
Top guest favourite
Home in Torrington
Enjoy the NW Hills, then relax by the river…
3 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
4.96 out of 5 average rating, 25 reviews
Guest favourite
Home in Sheffield
Berkshires Retreat w/ Pickleball – for Big Groups!
7 bedrooms, 8 beds, 3.5 bathrooms
15–20 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Salisbury
Lakeville Lodge with Private Pool
3 bedrooms, 4 beds, 2 bathrooms
22–27 Sept
4.92 out of 5 average rating, 25 reviews
Top guest favourite
Home in East Canaan
Spacious Home nestled along the Blackberry river.
3 bedrooms, 5 beds, 3 bathrooms
22–27 Sept
4.98 out of 5 average rating, 49 reviews
Guest favourite
Home in Sheffield
Bull Hill Bungalow
3 bedrooms, 3 beds, 2 bathrooms
22–27 Sept
4.98 out of 5 average rating, 55 reviews