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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, 186 reviews
Top guest favourite
Guest house in Canaan
Berkshires Retreat: Treetop Guest House + Gardens
2 bedrooms, 3 beds
24–29 Aug
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Place to stay in Canaan
Serene Berkshire Room with breakfast
1 bedroom, 1 queen bed
13–18 Aug
4.94 out of 5 average rating, 104 reviews
Top guest favourite
Home in Canaan
Secluded Mountain and Lake View in Canaan, NY
3 bedrooms, 3 beds
13–18 Sept
4.95 out of 5 average rating, 39 reviews
Top guest favourite
Cabin in Canaan
Newly Renovated Cabin in the Country
3 bedrooms, 3 beds
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
23–28 Aug
4.96 out of 5 average rating, 50 reviews
Top guest favourite
Home in Canaan
NEW! Berkshires Farmhouse w/ Firepit & Wood Stove
3 bedrooms, 5 beds
29 Aug – 3 Sept
4.99 out of 5 average rating, 116 reviews
Guest favourite
Earthen home in Canaan
Guest Eco Studio w/ Pool & Sauna on 100+ Acres
1 bedroom, 1 bed
16–21 Aug
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Canaan
Cozy modern Berkshire home with sauna & fire pit
3 bedrooms, 3 beds
8–13 Sept
4.97 out of 5 average rating, 62 reviews
Guest favourite
Chalet in Canaan
Sunset Ridge Chalet•Berkshires• Queechy Lake•HRV
2 bedrooms, 2 queen beds
25–30 Aug
4.9 out of 5 average rating, 21 reviews
Guest favourite
Rooms in Canaan
EnSuite: 2 Bedrms/Private Bathrm/breakfast
2 bedrooms, 3 beds
14–19 Aug
4.98 out of 5 average rating, 41 reviews
Top guest favourite
Cottage in Canaan
Private Berkshire Cottage with Queechy Lake Views
3 bedrooms, 4 beds
8–13 Sept
4.97 out of 5 average rating, 32 reviews
Top guest favourite
Home in Canaan
Crossings Cottage
2 bedrooms, 2 beds
13–18 Sept
4.97 out of 5 average rating, 90 reviews
Top guest favourite
Home in Canaan
Berkshire Lake House, gunite pool, Chef's Kitchen
7 bedrooms, 12 beds
14–19 Sept
4.99 out of 5 average rating, 101 reviews
Top guest favourite
Flat in East Chatham
Bennett Abode
1 bedroom, 1 double bed
6–11 Sept
4.96 out of 5 average rating, 179 reviews
Guest favourite
Cottage in Canaan
Berkshires Lake House Private Dock Kayaks Sleeps 6
3 bedrooms, 4 beds
13–18 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Cabin in Spencertown
Wake Up in the Woods, A Summer Reset Upstate
3 bedrooms, 4 beds
23–28 Aug
4.97 out of 5 average rating, 30 reviews
Top guest favourite
Barn in East Chatham
The Loft @ Sweet Pea Farms
1 bedroom, 2 queen beds
28 Aug – 2 Sept
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Cottage in New Lebanon
The Writer's Cottage
2 bedrooms, 2 beds
10–15 Sept
4.94 out of 5 average rating, 214 reviews