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Search results; Over 1,000 homes in Chatham

Top guest favourite
Cabin in Chatham
The Upstate Cabin: A secluded getaway in the woods
2 bedrooms, 2 beds, 1 private bathroom
26 Sept – 1 Oct
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4.98 out of 5 average rating, 160 reviews
Top guest favourite
Tiny home in Chatham
Boutique TINY home+private HOT TUB-walk to Main St
1 bedroom, 1 queen bed, 1 bathroom
1–6 Nov
4.99 out of 5 average rating, 379 reviews
Top guest favourite
Tiny home in Chatham
Romantic-Private-Western Tiny Cabin w/HOT TUB
1 bed, 1 bathroom
1–6 Nov
5.0 out of 5 average rating, 105 reviews
Top guest favourite
Flat in Chatham
Private Penthouse Apt in Historic Landmark 3-BR
3 bedrooms, 3 beds, 1.5 bathrooms
26–31 Oct
4.97 out of 5 average rating, 64 reviews
Top guest favourite
Flat in Chatham
'The Baker's Loft' 3BR Flat in Chatham Village, NY
3 bedrooms, 3 beds, 1 bathroom
12–17 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Loft in Chatham
unique 2000 sq ft 3 bedroom loft
3 bedrooms, 3 beds, 2 bathrooms
12–17 Sept
5.0 out of 5 average rating, 17 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, 36 reviews
Top guest favourite
Home in Chatham
Modern Log Chalet-Sauna & Pond on 10 private acres
3 bedrooms, 6 beds, 2.5 bathrooms
12–17 Sept
4.89 out of 5 average rating, 35 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, 84 reviews
Top guest favourite
Home in Town of Hillsdale
Gorgeous Mountain Views Retreat: Family & Nature
4 bedrooms, 5 beds, 2.5 bathrooms
13–18 Sept
4.98 out of 5 average rating, 83 reviews
Guest favourite
Home in Chatham
Beautiful Lake/Mountain Views. Bright Sunlit Home
4 bedrooms, 9 beds, 3.5 bathrooms
16–21 Sept
5.0 out of 5 average rating, 18 reviews
Guest favourite
Flat in Chatham
Chatham Village Library Flat
2 bedrooms, 3 beds, 1 bathroom
1–6 Dec
4.88 out of 5 average rating, 8 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 Canaan
Newly Renovated Cabin in the Country
3 bedrooms, 3 beds, 1 bathroom
14–19 Sept
4.96 out of 5 average rating, 196 reviews
Top guest favourite
Home in Ghent
Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi
2 bedrooms, 2 queen beds, 1 bathroom
2–7 Nov
4.95 out of 5 average rating, 286 reviews
Top guest favourite
Home in Old Chatham
Old Chatham Retreat | Skylight Over the King Bed
2 bedrooms, 2 beds, 2.5 bathrooms
15–20 Sept
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Rooms in Town of Hillsdale
Bellwether on Main, Passive House & AAC
2 bedrooms, 2 queen beds, 2 bathrooms
12–17 Sept
5.0 out of 5 average rating, 11 reviews
Guest favourite
Rooms in Kinderhook
Kinderhook Farmhouse w/ Pool!!
2 bedrooms, 2 beds, 2 bathrooms
13–18 Sept
4.86 out of 5 average rating, 28 reviews
Guest favourite
Home in Ghent
Luxury Modern 5 BR Retreat close to Hudson & Ski
5 bedrooms, 5 beds, 3.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 61 reviews