filters

Search results; Over 1,000 homes in Canaan

Descriptions are based on details hosts provide
Guest favourite
Home in Canaan
Berkshire Lakefront House with Amazing Views
3 bedrooms, 4 beds, 2 private bathrooms
9–14 Sept
,
4.91 out of 5 average rating, 182 reviews
Guest favourite
Guest house in Canaan
Berkshires Retreat: Treetop Guest House + Gardens
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
Guest favourite
Home in Canaan
Sauna, hot tub, and a fire pit
4.96 out of 5 average rating, 47 reviews, 5 bedrooms, 5 beds, 3 bathrooms
20–25 Jul
Top guest favourite
Home in Canaan
Lake views and a wrap-around deck
4.95 out of 5 average rating, 38 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
28 Aug – 2 Sept
Top guest favourite
Place to stay in Canaan
Serene Berkshire Room with breakfast
4.94 out of 5 average rating, 104 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Aug
Guest favourite
Chalet in Canaan
Sunset Ridge Chalet•Berkshires• Queechy Lake•HRV
4.89 out of 5 average rating, 19 reviews, 2 bedrooms, 2 beds, 3 bathrooms
21–26 Jul
Top guest favourite
Cottage in Canaan
Lake views and a deck with fire pit
4.97 out of 5 average rating, 32 reviews, 3 bedrooms, 4 beds, 1 bathroom
8–13 Sept
Top guest favourite
Home in Canaan
Secluded midcentury modern with barrel sauna
4.97 out of 5 average rating, 59 reviews, 3 bedrooms, 3 beds, 3 bathrooms
23–28 Aug
Top guest favourite
Cabin in Canaan
Newly Renovated Cabin in the Country
4.97 out of 5 average rating, 188 reviews, 3 bedrooms, 3 beds, 1 bathroom
23–28 Aug
Guest favourite
Room in East Chatham
Handcrafted bed in a post-and-beam inn
4.82 out of 5 average rating, 11 reviews, 1 king bed, 1 bathroom
26–31 Jul
Top guest favourite
Flat in New Lebanon
1830 Victorian with private garden, lake access
5.0 out of 5 average rating, 31 reviews, 1 bedroom, 2 beds, 1 bathroom
28 Aug – 2 Sept
Top guest favourite
Cottage in New Lebanon
19th-century cottage with orchard and loft
4.94 out of 5 average rating, 214 reviews, 2 bedrooms, 2 beds, 1 bathroom
31 Aug – 5 Sept
Guest favourite
Rooms in Canaan
4 acres with a pond and fire pit
4.98 out of 5 average rating, 41 reviews, 2 bedrooms, 3 beds, 1 bathroom
24–29 Aug
Top guest favourite
Barn in East Chatham
The Loft @ Sweet Pea Farms
5.0 out of 5 average rating, 46 reviews, 1 bedroom, 2 beds, 1 bathroom
28 Aug – 2 Sept
Top guest favourite
Home in Canaan
Panoramic views over 50+ acres
4.97 out of 5 average rating, 90 reviews, 2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
Top guest favourite
Flat in New Lebanon
1900 Greek Revival with high ceilings
4.97 out of 5 average rating, 117 reviews, 2 bedrooms, 3 beds, 1 bathroom
28 Aug – 2 Sept
Top guest favourite
Home in Canaan
Lake house with pool and private dock
4.99 out of 5 average rating, 101 reviews, 7 bedrooms, 12 beds, 2.5 bathrooms
8–15 Sept
Top guest favourite
Home in Canaan
Renovated farmhouse with pond views and fire pit
4.99 out of 5 average rating, 115 reviews, 3 bedrooms, 5 beds, 2 bathrooms
25–30 Jul
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
5.0 out of 5 average rating, 26 reviews, 2 bedrooms, 2 beds, 1 bathroom
27 Aug – 1 Sept