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Search results; Over 1,000 homes in Chatham Center

Guest favourite
Cottage in Chatham Center
Kinderhook Creek Private Retreat
2 bedrooms, 3 beds, 2 private bathrooms
29 Sept – 4 Oct
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4.87 out of 5 average rating, 183 reviews
Top guest favourite
Farm stay in Valatie
Hudson Valley Working Farm Stay
2 bedrooms, 2 queen beds, 1 bathroom
15–20 Sept
4.99 out of 5 average rating, 71 reviews
Top guest favourite
Home in Old Chatham
Monk's Bunk, Old Chatham
3 bedrooms, 6 beds, 2 bathrooms
14–19 Oct
5.0 out of 5 average rating, 35 reviews
Top guest favourite
Cabin in Spencertown
Wake Up in the Woods · A Cozy Fall Escape
3 bedrooms, 4 beds, 2 bathrooms
25–30 Sept
4.97 out of 5 average rating, 35 reviews
Top guest favourite
Cabin in East Nassau
Fall Foliage Luxury Cabin & View Autumn Adventures
3 bedrooms, 3 beds, 2 bathrooms
25–30 Oct
4.97 out of 5 average rating, 109 reviews
Top guest favourite
Barn in Stuyvesant
Pond Side R & R
3 bedrooms, 4 beds, 3.5 bathrooms
19–24 Oct
5.0 out of 5 average rating, 138 reviews
Top guest favourite
Guest suite in Valatie
Guest Suite in Old Chatham Hunt Country
1 bedroom, 1 queen bed, 1 bathroom
27 Sept – 2 Oct
4.98 out of 5 average rating, 294 reviews
Top guest favourite
Tiny home in Chatham
Sugar Shack | Romantic Tiny Home + Hot Tub
1 bedroom, 1 queen bed, 1 bathroom
27 Oct – 1 Nov
4.99 out of 5 average rating, 514 reviews
Top guest favourite
Room in North Chatham
Arnold Farmhouse (Italianate - private bath)
1 queen bed, 1 bathroom
20–25 Sept
4.94 out of 5 average rating, 408 reviews
Guest favourite
Guest house in Canaan
Berkshires Retreat: Treetop Guest House + Gardens
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
4.94 out of 5 average rating, 16 reviews
Top guest favourite
Home in Canaan
Secluded Mountain and Lake View in Canaan, NY
3 bedrooms, 3 beds, 3.5 bathrooms
28 Sept – 3 Oct
4.95 out of 5 average rating, 44 reviews
Top guest favourite
Cabin in Canaan
Newly Renovated Cabin in the Country
3 bedrooms, 3 beds, 1 bathroom
15–20 Sept
4.96 out of 5 average rating, 196 reviews
Top guest favourite
Loft in Chatham
unique 2000 sq ft 3 bedroom loft
3 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Ghent
Cozy Country Cape House | Close to Hudson
4 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 75 reviews
Top guest favourite
Home in Malden Bridge
Luxe upstate retreat with sauna on 20 acres
4 bedrooms, 6 beds, 3.5 bathrooms
24–29 Sept
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Guest house in Athens
Athens Cottage
2 bedrooms, 3 beds, 1 bathroom
14–19 Nov
4.98 out of 5 average rating, 87 reviews
Top guest favourite
Home in East Chatham
Secluded Chatham Oasis-Hot Tub+Treehouse+Pets
3 bedrooms, 4 beds, 2.5 bathrooms
16–21 Sept
5.0 out of 5 average rating, 43 reviews
Top guest favourite
Home in Old Chatham
Old Chatham Retreat | Skylight Over the King Bed
2 bedrooms, 2 beds, 2.5 bathrooms
25–30 Sept
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Room in North Chatham
Charming Eyebrow Colonial North Chatham, NY
1 king bed, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 629 reviews