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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
13–18 Sept
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4.99 out of 5 average rating, 282 reviews
Top guest favourite
Tiny home in Chatham
Boutique TINY home+private HOT TUB-walk to Main St
1 bedroom, 1 queen bed
23–28 Aug
4.99 out of 5 average rating, 371 reviews
Top guest favourite
Tiny home in Chatham
Romantic-Private-Western Tiny Cabin w/HOT TUB
1 bed
30 Aug – 4 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
23–28 Aug
4.97 out of 5 average rating, 61 reviews
Top guest favourite
Home in Chatham
Modern Log Chalet-Sauna & Pond on 10 private acres
3 bedrooms, 6 beds
30 Aug – 4 Sept
4.87 out of 5 average rating, 31 reviews
Luxe
Home in Chatham
Modern retreat, Catskill views from Pool & Hot Tub
5 bedrooms, 7 beds
22–27 Sept
5.0 out of 5 average rating, 35 reviews
Guest favourite
Home in Chatham
Beautiful Lake/Mountain Views. Bright Sunlit Home
4 bedrooms, 9 beds
26–31 Aug
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Flat in Chatham
'The Baker's Loft' 3BR Flat in Chatham Village, NY
3 bedrooms, 3 beds
16–21 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Loft in Chatham
unique 2000 sq ft 3 bedroom loft
3 bedrooms, 3 beds
17–22 Aug
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Guest house in Stuyvesant
The Falls at Lindenwald Cottage
1 bedroom, 2 beds
7–12 Sept
5.0 out of 5 average rating, 72 reviews
Top guest favourite
Room in North Chatham
Arnold Farmhouse (Italianate - private bath)
1 queen bed
10–15 Aug
4.94 out of 5 average rating, 401 reviews
Top guest favourite
Home in Ghent
Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi
2 bedrooms, 2 queen beds
2–7 Nov
4.95 out of 5 average rating, 284 reviews
Guest favourite
Townhouse in Hudson
Chic Hot Tub Escape | PetFriendly | Hudson, NY
2 bedrooms, 2 beds
13–18 Sept
4.93 out of 5 average rating, 105 reviews
Top guest favourite
Guest house in Canaan
Berkshires Retreat: Treetop Guest House + Gardens
2 bedrooms, 3 beds
24–29 Aug
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Barn in Stuyvesant
Pond Side R & R
3 bedrooms, 4 beds
8–13 Sept
5.0 out of 5 average rating, 136 reviews
Top guest favourite
Home in East Jewett
Creekside Couple's Escape w/ Hot Tub Sauna & More!
1 bedroom, 2 beds
1–6 Nov
4.95 out of 5 average rating, 21 reviews
Top guest favourite
Farm stay in Chatham
Cozy, Charming Cabin Studio in Prime Hudson Valley
1 bedroom, 1 king bed
24–29 Aug
4.99 out of 5 average rating, 80 reviews
Top guest favourite
Cabin in Chatham
The Upstate Cabin: A secluded getaway in the woods
2 bedrooms, 2 queen beds
24–29 Aug
4.97 out of 5 average rating, 158 reviews
Top guest favourite
Barn in East Chatham
The Loft @ Sweet Pea Farms
1 bedroom, 2 queen beds
28 Aug – 2 Sept
5.0 out of 5 average rating, 49 reviews