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Search results; Over 1,000 homes in Canaan

Top guest favourite
Cottage in Canaan
The Cottage at Great Falls Luxury Getaway.
2 bedrooms, 2 beds, 1 shared bathroom
29 Sept – 4 Oct
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4.98 out of 5 average rating, 122 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
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, 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
Cottage in Sheffield
The Blue Elm - A Historic Country Cottage
1 bedroom, 2 beds, 1.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 101 reviews
Top guest favourite
Home in Salisbury
Under Mountain House
3 bedrooms, 3 beds, 3 bathrooms
11–16 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
11–16 Sept
4.98 out of 5 average rating, 52 reviews
Top guest favourite
Home in Canaan
Summer under the Stars
3 bedrooms, 6 beds, 2.5 bathrooms
12–17 Sept
4.97 out of 5 average rating, 35 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
Guest favourite
Cabin in Cornwall
Mountain Cabin With Rustic Charm & New Fire Pit!
3 bedrooms, 3 queen beds, 1.5 bathrooms
28 Sept – 3 Oct
4.85 out of 5 average rating, 82 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
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
Guest favourite
Home in Sheffield
Bull Hill Bungalow
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 55 reviews
Guest favourite
Cottage in New Marlborough
Gravel bike dream location!
2 bedrooms, 3 beds, 1 bathroom
11–16 Sept
5.0 out of 5 average rating, 63 reviews
Guest favourite
Home in New Marlborough
Cottage in the heart of Mill River Village
2 bedrooms, 2 queen beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 41 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
Cottage in Litchfield County
Cozy Cottage in Historic Norfolk
2 bedrooms, 3 beds, 1.5 bathrooms
1–6 Jan
5.0 out of 5 average rating, 14 reviews