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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
24–29 Aug
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4.97 out of 5 average rating, 158 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
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, 1 bathroom
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, 1.5 bathrooms
26–31 Aug
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
16–21 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Loft in Chatham
unique 2000 sq ft 3 bedroom loft
3 bedrooms, 3 beds, 2 bathrooms
17–22 Aug
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
30 Aug – 4 Sept
4.88 out of 5 average rating, 32 reviews
Top guest favourite
Farm stay in Chatham
Cozy, Charming Cabin Studio in Prime Hudson Valley
1 bedroom, 1 king bed, 1 bathroom
24–29 Aug
4.99 out of 5 average rating, 80 reviews
Top guest favourite
Room in North Chatham
Arnold Farmhouse (Italianate - private bath)
1 queen bed, 1 bathroom
23–28 Aug
4.94 out of 5 average rating, 402 reviews
Top guest favourite
Guest house in Athens
Athens Cottage
2 bedrooms, 3 beds, 1 bathroom
21–26 Sept
4.97 out of 5 average rating, 73 reviews
Top guest favourite
Room in North Chatham
Charming Eyebrow Colonial North Chatham, NY
1 king bed, 1 bathroom
30 Aug – 4 Sept
4.97 out of 5 average rating, 615 reviews
Guest favourite
Guest house in Canaan
Berkshires Retreat: Treetop Guest House + Gardens
2 bedrooms, 3 beds, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 13 reviews
Guest favourite
Home in Chatham
Beautiful Lake/Mountain Views. Bright Sunlit Home
4 bedrooms, 9 beds, 3.5 bathrooms
26–31 Aug
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Guest house in Chatham
Tranquil Guest House, Chatham NY
2 bedrooms, 3 beds, 1 bathroom
1–6 Mar
4.94 out of 5 average rating, 53 reviews
Guest favourite
Flat in Valatie
Boho Bungalow Apartment
2 bedrooms, 2 queen beds, 1.5 bathrooms
18–23 Aug
4.92 out of 5 average rating, 24 reviews
Guest favourite
Farm stay in New Lebanon
NEW RENO - Chalet-style farm loft near Tanglewood
1 bedroom, 3 beds, 1 bathroom
16–21 Aug
4.91 out of 5 average rating, 70 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, 284 reviews
Top guest favourite
Flat in New Lebanon
Folk Art Studio: 1-bedroom near the Berkshires
1 bedroom, 2 beds, 1 bathroom
5–10 Sept
5.0 out of 5 average rating, 31 reviews
Top guest favourite
Place to stay in Town of Hillsdale
Sun Filled Historic Retreat | Berkshires & Hudson
1 bedroom, 1 queen bed, 1 bathroom
16–21 Aug
4.94 out of 5 average rating, 101 reviews