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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
9–14 Sept
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4.91 out of 5 average rating, 184 reviews
Top guest favourite
Place to stay in Canaan
Serene Berkshire Room with breakfast
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
4.94 out of 5 average rating, 104 reviews
Guest favourite
Guest house in Canaan
Berkshires Retreat: Treetop Guest House + Gardens
2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Canaan
Secluded Mountain and Lake View in Canaan, NY
3 bedrooms, 3 beds, 3.5 bathrooms
4–9 Sept
4.95 out of 5 average rating, 39 reviews
Guest favourite
Rooms in Canaan
EnSuite: 2 Bedrms/Private Bathrm/breakfast
2 bedrooms, 3 beds, 1 bathroom
24–29 Aug
4.98 out of 5 average rating, 41 reviews
Guest favourite
Chalet in Canaan
Sunset Ridge Chalet•Berkshires• Queechy Lake•HRV
2 bedrooms, 2 queen beds, 3 bathrooms
2–7 Aug
4.89 out of 5 average rating, 19 reviews
Guest favourite
Earthen home in Canaan
Guest Eco Studio w/ Pool & Sauna on 100+ Acres
1 bedroom, 1 bed, 1 bathroom
8–13 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Flat in East Chatham
Bennett Abode
1 bedroom, 1 double bed, 1.5 bathrooms
2–7 Aug
4.96 out of 5 average rating, 175 reviews
Top guest favourite
Home in Canaan
Cozy modern Berkshire home with sauna & fire pit
3 bedrooms, 3 beds, 3 bathrooms
22–27 Aug
4.97 out of 5 average rating, 60 reviews
Top guest favourite
Cottage in Canaan
Private Berkshire Cottage with Queechy Lake Views
3 bedrooms, 4 beds, 1 bathroom
8–13 Sept
4.97 out of 5 average rating, 32 reviews
Top guest favourite
Guest suite in Lenox
High Above Cliffwood (Full Apartment)
1 bedroom, 1 king bed, 1 bathroom
20–25 Aug
4.92 out of 5 average rating, 24 reviews
Top guest favourite
Cabin in Canaan
Newly Renovated Cabin in the Country
3 bedrooms, 3 beds, 1 bathroom
23–28 Aug
4.97 out of 5 average rating, 190 reviews
Top guest favourite
Flat in Lenox
Main Street Delight One Bedroom Apartment
1 bedroom, 1 queen bed, 1 bathroom
26–31 Oct
4.98 out of 5 average rating, 90 reviews
Guest favourite
Home in Canaan
The Little Yellow Door
5 bedrooms, 5 beds, 3 bathrooms
23–28 Aug
4.96 out of 5 average rating, 48 reviews
Top guest favourite
Home in East Chatham
Charming house in historic hamlet
3 bedrooms, 4 beds, 1.5 bathrooms
5–10 Aug
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds, 1 bathroom
27 Aug – 1 Sept
5.0 out of 5 average rating, 30 reviews
Guest favourite
Room in Old Chatham
Haddock Hill House
2 beds, 1 bathroom
1–6 Aug
4.89 out of 5 average rating, 53 reviews
Top guest favourite
Guest suite in Valatie
Guest Suite in Old Chatham Hunt Country
1 bedroom, 1 queen bed, 1 bathroom
1–6 Aug
4.98 out of 5 average rating, 285 reviews
Top guest favourite
Barn in East Chatham
The Loft @ Sweet Pea Farms
1 bedroom, 2 queen beds, 1 bathroom
28 Aug – 2 Sept
5.0 out of 5 average rating, 48 reviews