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Search results; Over 1,000 homes in Chatham

Top guest favourite
Cabin in Chatham
Rustic Secluded Cabin near Berkshires. *wood stove
4 bedrooms, 3 beds, 1.5 private bathrooms
8–13 Sept
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4.92 out of 5 average rating, 144 reviews
Top guest favourite
Cabin in Chatham
A-Frame + Private Hot Tub + Walk to Main St
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Tiny home in Chatham
Romantic-Private-Western Tiny Cabin w/HOT TUB
1 bed, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 103 reviews
Guest favourite
Serviced apartment in Chatham
Private Penthouse Apt in Historic Landmark 3-BR
3 bedrooms, 3 beds, 1.5 bathrooms
9–14 Sept
4.97 out of 5 average rating, 61 reviews
Top guest favourite
Flat in Chatham
'The Baker's Loft' 3BR Flat in Chatham Village, NY
3 bedrooms, 3 beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Farm stay in Chatham
Cozy, Charming Cabin Studio in Prime Hudson Valley
1 bedroom, 1 king bed, 1 bathroom
27 Sept – 2 Oct
4.99 out of 5 average rating, 80 reviews
Top guest favourite
Home in Old Chatham
Monk's Bunk, Old Chatham
3 bedrooms, 6 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Loft in Chatham
unique 2000 sq ft 3 bedroom loft
3 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Chatham
Modern Log Chalet-Sauna & Pond on 10 private acres
3 bedrooms, 6 beds, 2.5 bathrooms
1–6 Sept
4.88 out of 5 average rating, 32 reviews
Luxe
Home in Chatham
Modern retreat, Catskill views from Pool & Hot Tub
5 bedrooms, 7 beds, 4.5 bathrooms
22–27 Sept
5.0 out of 5 average rating, 35 reviews
Top guest favourite
Flat in East Chatham
Bennett Abode
1 bedroom, 1 double bed, 1.5 bathrooms
6–11 Sept
4.96 out of 5 average rating, 183 reviews
Top guest favourite
Room in North Chatham
Charming Eyebrow Colonial North Chatham, NY
1 king bed, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 622 reviews
Top guest favourite
Guest suite in Valatie
Guest Suite in Old Chatham Hunt Country
1 bedroom, 1 queen bed, 1 bathroom
6–11 Sept
4.98 out of 5 average rating, 290 reviews
Top guest favourite
Guest house in Canaan
Berkshires Retreat: Treetop Guest House + Gardens
2 bedrooms, 3 beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Guest house in Athens
Athens Cottage
2 bedrooms, 3 beds, 1 bathroom
4–9 Nov
4.97 out of 5 average rating, 76 reviews
Top guest favourite
Cabin in Chatham
The Upstate Cabin: A secluded getaway in the woods
2 bedrooms, 2 queen beds, 1 bathroom
8–13 Sept
4.97 out of 5 average rating, 159 reviews
Top guest favourite
Home in Hudson
Chic Hudson Farmhouse w/ Fireplace & Porch
3 bedrooms, 3 beds, 1.5 bathrooms
7–13 Sept
4.98 out of 5 average rating, 123 reviews
Top guest favourite
Room in North Chatham
Arnold Farmhouse (Italianate - private bath)
1 queen bed, 1 bathroom
6–11 Sept
4.94 out of 5 average rating, 405 reviews
Guest favourite
Home in Chatham
Beautiful Lake/Mountain Views. Bright Sunlit Home
4 bedrooms, 9 beds, 3.5 bathrooms
9–14 Sept
5.0 out of 5 average rating, 17 reviews