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Search results; Over 1,000 homes in Canaan

Guest favourite
Guest house in Canaan
Airy cottage with meadow views in The Berkshires
1 bedroom, 3 beds, 1 private bathroom
8–13 Sept
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4.93 out of 5 average rating, 214 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, 41 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
Top guest favourite
Guest house in Canaan
Berkshires Retreat: Treetop Guest House + Gardens
2 bedrooms, 3 beds
3–8 Sept
5.0 out of 5 average rating, 14 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
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
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
The Little Yellow Door
5 bedrooms, 5 beds
23–28 Aug
4.96 out of 5 average rating, 52 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, 105 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
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, 11 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
Guest favourite
Farm stay in New Lebanon
NEW RENO - Chalet-style farm loft near Tanglewood
1 bedroom, 3 beds
22–27 Aug
4.92 out of 5 average rating, 72 reviews
Top guest favourite
Home in Canaan
Berkshire Queechy Lake Haven
2 bedrooms, 2 queen beds
8–13 Sept
5.0 out of 5 average rating, 15 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
Guest favourite
Bed and breakfast in East Chatham
The Inn at Silver Maple Farm - Silver Maple
1 bedroom, 1 king bed
23–28 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Pittsfield
Cantabile life in the Berkshires
3 bedrooms, 5 beds
11–16 Sept
4.96 out of 5 average rating, 229 reviews
Guest favourite
Cabin in East Nassau
Fall Foliage Luxury Cabin & View Autumn Adventures
3 bedrooms, 3 beds
25–30 Oct
4.97 out of 5 average rating, 102 reviews