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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, 183 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
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
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
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
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
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
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
Guest house in Canaan
New-Modern Guesthouse
2 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
5.0 out of 5 average rating, 35 reviews
Top guest favourite
Home in Canaan
NEW! Berkshires Farmhouse w/ Firepit & Wood Stove
3 bedrooms, 5 beds, 2 bathrooms
27 Aug – 1 Sept
4.99 out of 5 average rating, 116 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
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
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
Cottage in Canaan
Berkshires Lake House Private Dock Kayaks Sleeps 6
3 bedrooms, 4 beds, 1.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in New Lebanon
The old sawmill from 1771
1 bedroom, 2 beds, 2 bathrooms
5–10 Sept
4.99 out of 5 average rating, 383 reviews
Home in New Lebanon
Above the Clouds Mountain Retreat
3 bedrooms, 3 beds, 4 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Cabin in Spencertown
Wake Up in the Woods, A Summer Reset Upstate
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.97 out of 5 average rating, 29 reviews
Top guest favourite
Home in Canaan
Berkshire Lake House, gunite pool, Chef's Kitchen
7 bedrooms, 12 beds, 2.5 bathrooms
14–19 Sept
4.99 out of 5 average rating, 101 reviews
Top guest favourite
Home in Canaan
Berkshire Queechy Lake Haven
2 bedrooms, 2 queen beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 15 reviews