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Search results; Over 1,000 homes in Canaan

Guest favourite
Home in Canaan
Berkshire Lakefront House with Amazing Views
3 bedrooms, 4 beds, 2 private bathrooms
23–28 Sept
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4.91 out of 5 average rating, 187 reviews
Top guest favourite
Home in Canaan
Secluded Mountain and Lake View in Canaan, NY
3 bedrooms, 3 beds, 3.5 bathrooms
28 Sept – 3 Oct
4.95 out of 5 average rating, 44 reviews
Guest favourite
Home in Canaan
The Little Yellow Door
5 bedrooms, 5 beds, 3 bathrooms
12–17 Sept
4.96 out of 5 average rating, 53 reviews
Top guest favourite
Home in Canaan
Relax and Rejuvenate at Fox Hollow Cottage
3 bedrooms, 4 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Cabin in Canaan
Newly Renovated Cabin in the Country
3 bedrooms, 3 beds, 1 bathroom
14–19 Sept
4.96 out of 5 average rating, 196 reviews
Top guest favourite
Home in Canaan
Berkshire Lake House, gunite pool, Chef's Kitchen
7 bedrooms, 12 beds, 2.5 bathrooms
20–25 Sept
4.99 out of 5 average rating, 101 reviews
Top guest favourite
Home in Canaan
NEW! Berkshires Farmhouse w/ Firepit & Wood Stove
3 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.99 out of 5 average rating, 120 reviews
Top guest favourite
Home in Canaan
Cozy modern Berkshire home with sauna & fire pit
3 bedrooms, 3 beds, 3 bathrooms
19–24 Oct
4.97 out of 5 average rating, 63 reviews
Top guest favourite
Home in Canaan
Crossings Cottage
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 90 reviews
Top guest favourite
Place to stay in Canaan
Serene Berkshire Room with breakfast
1 bedroom, 1 queen bed, 1 bathroom
11–16 Oct
4.94 out of 5 average rating, 105 reviews
Top guest favourite
Home in Canaan
Hiking Nearby! Hot Tub, Movie & Game Room!
3 bedrooms, 3 beds, 2 bathrooms
21–26 Sept
4.97 out of 5 average rating, 87 reviews
Guest favourite
Earthen home in Canaan
Chic Eco Studio | Fall Foliage | Pool + Sauna
1 bedroom, 1 bed, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Barn in East Chatham
The Loft @ Sweet Pea Farms
1 bedroom, 2 queen beds, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 52 reviews
Top guest favourite
Guest house in Canaan
New-Modern Guesthouse
2 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
5.0 out of 5 average rating, 39 reviews
Top guest favourite
Home in East Chatham
Charming house in historic hamlet
3 bedrooms, 4 beds, 1.5 bathrooms
15–20 Sept
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Cabin in Spencertown
Wake Up in the Woods · A Cozy Fall Escape
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.97 out of 5 average rating, 35 reviews
Cabin in Canaan
Maison des Ardennes: Cabin Retreat in Canaan
2 bedrooms, 2 king beds, 2 bathrooms
18–23 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Richmond
Bucolic Pet Friendly Oasis | 10 min to Tanglewood
4 bedrooms, 4 beds, 2 bathrooms
24–29 Sept
4.97 out of 5 average rating, 33 reviews
Guest favourite
Home in Canaan
Peaceful Berkshire Getaway (A/C, Lake Access)
4 bedrooms, 4 beds, 2 bathrooms
5–10 Oct
4.96 out of 5 average rating, 77 reviews