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Search results; Over 1,000 homes in Canaan

Top guest favourite
Cabin in Canaan
Newly Renovated Cabin in the Country
3 bedrooms, 3 beds, 1 private bathroom
23–28 Aug
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4.97 out of 5 average rating, 189 reviews
Top guest favourite
Home in Canaan
Secluded Mountain and Lake View in Canaan, NY
4.95 out of 5 average rating, 38 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
8–13 Sept
Guest favourite
Guest house in Canaan
Berkshires Retreat: Treetop Guest House + Gardens
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 3 beds, 1 bathroom
26–31 Jul
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
Private Berkshire Cottage with Queechy Lake Views
4.97 out of 5 average rating, 32 reviews, 3 bedrooms, 4 beds, 1 bathroom
8–13 Sept
Guest favourite
Home in Canaan
The Little Yellow Door
4.96 out of 5 average rating, 47 reviews, 5 bedrooms, 5 beds, 3 bathrooms
20–25 Jul
Top guest favourite
Home in Canaan
Cozy modern Berkshire home with sauna & fire pit
4.97 out of 5 average rating, 59 reviews, 3 bedrooms, 3 beds, 3 bathrooms
23–28 Aug
Top guest favourite
Home in Canaan
NEW! Berkshires Farmhouse w/ Firepit & Wood Stove
4.99 out of 5 average rating, 116 reviews, 3 bedrooms, 5 beds, 2 bathrooms
27 Aug – 1 Sept
Guest favourite
Rooms in Canaan
EnSuite: 2 Bedrms/Private Bathrm/breakfast
4.98 out of 5 average rating, 41 reviews, 2 bedrooms, 3 beds, 1 bathroom
24–29 Aug
Guest favourite
Cottage in Canaan
Berkshires Lake House Private Dock Kayaks Sleeps 6
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
13–18 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
Top guest favourite
Home in New Lebanon
The old sawmill from 1771
4.99 out of 5 average rating, 382 reviews, 1 bedroom, 2 beds, 2 bathrooms
5–10 Sept
Top guest favourite
Home in Canaan
Crossings Cottage
4.97 out of 5 average rating, 90 reviews, 2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
Guest favourite
Cabin in East Nassau
The Kinderhook Cabin on the Kinderhook creek.
4.94 out of 5 average rating, 51 reviews, 3 bedrooms, 4 beds, 1 bathroom
31 Aug – 5 Sept
Top guest favourite
Home in Canaan
Berkshire Queechy Lake Haven
5.0 out of 5 average rating, 15 reviews, 2 bedrooms, 2 beds, 2 bathrooms
8–13 Sept
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
5.0 out of 5 average rating, 27 reviews, 2 bedrooms, 2 beds, 1 bathroom
27 Aug – 1 Sept
Top guest favourite
Home in Canaan
Berkshire Lake House, gunite pool, Chef's Kitchen
4.99 out of 5 average rating, 101 reviews, 7 bedrooms, 12 beds, 2.5 bathrooms
14–19 Sept
Home in New Lebanon
Above the Clouds Mountain Retreat
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 3 beds, 4 bathrooms
31 Aug – 5 Sept
Top guest favourite
Room in North Chatham
Charming Eyebrow Colonial North Chatham, NY
4.97 out of 5 average rating, 606 reviews, 1 king bed, 1 bathroom
9–14 Aug