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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
Tiny home in Chatham
Boutique TINY home+private HOT TUB-walk to Main St
4.99 out of 5 average rating, 366 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Aug
Top guest favourite
Tiny home in Chatham
Romantic-Private-Western Tiny Cabin w/HOT TUB
5.0 out of 5 average rating, 101 reviews, 1 bed, 1 bathroom
30 Aug – 4 Sept
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
Home in Chatham
Modern Log Chalet-Sauna & Pond on 10 private acres
4.87 out of 5 average rating, 30 reviews, 3 bedrooms, 6 beds, 2.5 bathrooms
9–14 Aug
Top guest favourite
Loft in Chatham
unique 2000 sq ft 3 bedroom loft
5.0 out of 5 average rating, 15 reviews, 3 bedrooms, 3 beds, 2 bathrooms
1–6 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
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
Top guest favourite
Flat in Chatham
'The Baker's Loft' 3BR Flat in Chatham Village, NY
5.0 out of 5 average rating, 7 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, 11 reviews, 2 bedrooms, 3 beds, 1 bathroom
24–29 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
19–24 Oct
Top guest favourite
Barn in Stuyvesant
Pond Side R & R
5.0 out of 5 average rating, 135 reviews, 3 bedrooms, 4 beds, 3.5 bathrooms
3–8 Aug
Top guest favourite
Barn in East Chatham
The Loft @ Sweet Pea Farms
5.0 out of 5 average rating, 48 reviews, 1 bedroom, 2 beds, 1 bathroom
28 Aug – 2 Sept
Top guest favourite
Room in North Chatham
Arnold Farmhouse (Italianate - private bath)
4.94 out of 5 average rating, 400 reviews, 1 queen bed, 1 bathroom
10–15 Aug
Guest favourite
Cottage in Craryville
Farm Cottage w/ Donkeys, Fire Pit & Wood Stove
4.91 out of 5 average rating, 594 reviews, 3 bedrooms, 3 beds, 2 bathrooms
2–7 Aug
Top guest favourite
Guest house in Athens
Athens Cottage
4.97 out of 5 average rating, 67 reviews, 2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
Top guest favourite
Farm stay in Chatham
Cozy, Charming Cabin Studio in Prime Hudson Valley
4.99 out of 5 average rating, 79 reviews, 1 bedroom, 1 bed, 1 bathroom
8–13 Sept
Top guest favourite
Home in Ghent
Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi
4.95 out of 5 average rating, 284 reviews, 2 bedrooms, 2 beds, 1 bathroom
8–13 Aug
Superhost
Home in Hudson
Designer Home, Hot Tub, Private Yard, & Projector
4.94 out of 5 average rating, 140 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
27 Sept – 2 Oct