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Search results; Over 1,000 homes in Canaan

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Guest favourite
Place to stay in Canaan
Serene Berkshire Room with breakfast
1 bedroom, 1 bed, 1 private bathroom
11–16 Oct
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4.94 out of 5 average rating, 105 reviews
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Top guest favourite
Home in Canaan
Secluded Mountain and Lake View in Canaan, NY
3 bedrooms, 3 beds, 3.5 bathrooms
1–6 Oct
4.96 out of 5 average rating, 45 reviews
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Guest favourite
Home in Canaan
The Little Yellow Door
5 bedrooms, 5 beds, 3 bathrooms
1–6 Oct
4.96 out of 5 average rating, 53 reviews
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Top guest favourite
Home in Canaan
Relax and Rejuvenate at Fox Hollow Cottage
3 bedrooms, 4 beds, 2 bathrooms
1–6 Nov
5.0 out of 5 average rating, 10 reviews
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Top guest favourite
Home in Canaan
Cozy modern Berkshire home with sauna & fire pit
3 bedrooms, 3 beds, 3 bathrooms
19–24 Oct
4.97 out of 5 average rating, 64 reviews
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Guest favourite
Guest house in Canaan
Berkshires Retreat: Treetop Guest House + Gardens
2 bedrooms, 3 beds, 1 bathroom
11–16 Oct
4.94 out of 5 average rating, 16 reviews
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Top guest favourite
Home in Canaan
Berkshire Lake House, gunite pool, Chef's Kitchen
7 bedrooms, 12 beds, 2.5 bathrooms
1–6 Oct
4.99 out of 5 average rating, 102 reviews
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Top guest favourite
Guest house in Canaan
New-Modern Guesthouse
2 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 40 reviews
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Top guest favourite
Cabin in Canaan
Newly Renovated Cabin in the Country
3 bedrooms, 3 beds, 1 bathroom
4–9 Oct
4.96 out of 5 average rating, 197 reviews
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Guest favourite
Earthen home in Canaan
Chic Eco Studio | Fall Foliage | Pool + Sauna
1 bedroom, 1 bed, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 12 reviews
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Guest favourite
Home in Canaan
Peaceful Berkshire Getaway (A/C, Lake Access)
4 bedrooms, 4 beds, 2 bathrooms
25–30 Oct
4.96 out of 5 average rating, 77 reviews
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Top guest favourite
Home in Canaan
NEW! Berkshires Farmhouse w/ Firepit & Wood Stove
3 bedrooms, 5 beds, 2 bathrooms
1–6 Nov
4.99 out of 5 average rating, 121 reviews
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Top guest favourite
Cottage in Canaan
Private Berkshire Cottage with Queechy Lake Views
3 bedrooms, 4 beds, 1 bathroom
1–6 Oct
4.97 out of 5 average rating, 33 reviews
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Cabin in Canaan
Maison des Ardennes: Cabin Retreat in Canaan
2 bedrooms, 2 king beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Canaan
Hiking Nearby! Hot Tub, Movie & Game Room!
3 bedrooms, 3 beds, 2 bathrooms
25–30 Oct
4.97 out of 5 average rating, 87 reviews
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Top guest favourite
Home in Canaan
Crossings Cottage
2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
4.97 out of 5 average rating, 91 reviews
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Guest favourite
Home in Richmond
Bucolic Pet Friendly Oasis | 10 min to Tanglewood
4 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
4.97 out of 5 average rating, 33 reviews
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Top guest favourite
Flat in East Chatham
Bennett Abode
1 bedroom, 1 double bed, 1.5 bathrooms
4–9 Oct
4.96 out of 5 average rating, 192 reviews
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Top guest favourite
Cabin in Spencertown
Wake Up in the Woods · A Cozy Fall Escape
3 bedrooms, 4 beds, 2 bathrooms
25–30 Oct
4.97 out of 5 average rating, 35 reviews