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Search results; Over 1,000 homes in Canaan

Home in Canaan
R3Bliss - Estate with Hot Tub, Tennis Court & Pool
4 bedrooms, 4 beds, 2.5 private bathrooms
1–6 Sept
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4.55 out of 5 average rating, 73 reviews
Guest favourite
Home in Canaan
Relax and Rejuvenate at Fox Hollow Cottage
3 bedrooms, 4 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 7 reviews
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
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, 40 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
Cozy modern Berkshire home with sauna & fire pit
3 bedrooms, 3 beds
8–13 Sept
4.97 out of 5 average rating, 62 reviews
Top guest favourite
Cabin in Canaan
Newly Renovated Cabin in the Country
3 bedrooms, 3 beds
23–28 Aug
4.96 out of 5 average rating, 192 reviews
Top guest favourite
Home in Canaan
The Little Yellow Door
5 bedrooms, 5 beds
23–28 Aug
4.96 out of 5 average rating, 51 reviews
Top guest favourite
Place to stay in Canaan
Serene Berkshire Room with breakfast
1 bedroom, 1 queen bed
23–28 Aug
4.94 out of 5 average rating, 104 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, 118 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
Guest favourite
Earthen home in Canaan
Guest Eco Studio w/ Pool & Sauna on 100+ Acres
1 bedroom, 1 bed
8–13 Sept
5.0 out of 5 average rating, 10 reviews
Guest favourite
Rooms in Canaan
EnSuite: 2 Bedrms/Private Bathrm/breakfast
2 bedrooms, 3 beds
18–23 Sept
4.98 out of 5 average rating, 41 reviews
Top guest favourite
Flat in New Lebanon
Folk Art Studio: 1-bedroom near the Berkshires
1 bedroom, 2 beds
4–9 Sept
5.0 out of 5 average rating, 31 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, 9 reviews
Top guest favourite
Home in Canaan
Berkshire Queechy Lake Haven
2 bedrooms, 2 queen beds
7–12 Sept
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Cabin in Chatham
A-Frame + Private Hot Tub + Walk to Main St
1 bedroom, 1 queen bed
27 Sept – 2 Oct
5.0 out of 5 average rating, 14 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, 32 reviews
Top guest favourite
Home in Pittsfield
Cozy cottage on peaceful pond
2 bedrooms, 2 beds
26–31 Oct
5.0 out of 5 average rating, 33 reviews