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Search results; Over 1,000 homes in Chatham

Top guest favourite
Tiny home in Chatham
Peaceful Tiny House Escape by Hudson & Berkshires
2 bedrooms, 2 beds, 1 shared bathroom
6–11 Sept
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4.99 out of 5 average rating, 279 reviews
Top guest favourite
Cabin in Chatham
A-Frame + Private Hot Tub + Walk to Main St
5.0 out of 5 average rating, 8 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Aug
Guest favourite
Serviced apartment in Chatham
Private Penthouse Apt in Historic Landmark 3-BR
4.97 out of 5 average rating, 60 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
23–28 Aug
Top guest favourite
Tiny home in Chatham
Romantic-Private-Western Tiny Cabin w/HOT TUB
5.0 out of 5 average rating, 99 reviews, 1 bed, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Home in Chatham
Modern Log Chalet-Sauna & Pond on 10 private acres
4.86 out of 5 average rating, 29 reviews, 3 bedrooms, 6 beds, 2.5 bathrooms
9–14 Aug
Top guest favourite
Guest house in Chatham
Tranquil Guest House, Chatham NY
4.94 out of 5 average rating, 53 reviews, 2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
Luxe
Home in Chatham
Modern retreat, Catskill views from Pool & Hot Tub
5.0 out of 5 average rating, 34 reviews, 5 bedrooms, 7 beds, 4.5 bathrooms
16–21 Sept
Top guest favourite
Loft in Chatham
unique 2000 sq ft 3 bedroom loft
5.0 out of 5 average rating, 14 reviews, 3 bedrooms, 3 beds, 2 bathrooms
1–6 Aug
Guest favourite
Home in Chatham
Beautiful Lake/Mountain Views. Bright Sunlit Home
5.0 out of 5 average rating, 16 reviews, 4 bedrooms, 9 beds, 3.5 bathrooms
26–31 Aug
Guest favourite
Flat in Chatham
'The Baker's Loft' 3BR Flat in Chatham Village, NY
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 3 beds, 1 bathroom
1–6 Aug
Guest favourite
Guest house in Canaan
Berkshires Retreat: Treetop Guest House + Gardens
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Top guest favourite
Farm stay in Chatham
Cozy, Charming Cabin Studio in Prime Hudson Valley
4.99 out of 5 average rating, 77 reviews, 1 bedroom, 1 bed, 1 bathroom
8–13 Sept
Top guest favourite
Barn in Town of Hillsdale
Blue Door Barn - Pond and Sweeping Views
5.0 out of 5 average rating, 11 reviews, 1 bedroom, 2 beds, 1 bathroom
17–22 Aug
Top guest favourite
Home in Old Chatham
Old Chatham Retreat | Skylight Over the King Bed
5.0 out of 5 average rating, 21 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
18–23 Aug
Top guest favourite
Home in Ghent
Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi
4.95 out of 5 average rating, 282 reviews, 2 bedrooms, 2 beds, 1 bathroom
8–13 Aug
Guest favourite
Cottage in Ghent
Light, airy cottage with pool 10 min from Hudson
4.76 out of 5 average rating, 17 reviews, 2 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
Top guest favourite
Room in North Chatham
Charming Eyebrow Colonial North Chatham, NY
4.97 out of 5 average rating, 607 reviews, 1 king bed, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Cabin in Chatham
The Upstate Cabin: A secluded getaway in the woods
4.97 out of 5 average rating, 158 reviews, 2 bedrooms, 2 beds, 1 bathroom
24–29 Aug
Top guest favourite
Cabin in Canaan
Newly Renovated Cabin in the Country
4.97 out of 5 average rating, 189 reviews, 3 bedrooms, 3 beds, 1 bathroom
23–28 Aug