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Search results; Over 1,000 homes in Chatham

Top guest favourite
Cabin in Chatham
Rustic Secluded Cabin near Berkshires. *wood stove
4 bedrooms, 3 beds, 1.5 private bathrooms
7–12 Sept
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4.92 out of 5 average rating, 143 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
30 Aug – 4 Sept
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
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
Guest favourite
Flat in Chatham
Chatham Village Library Flat
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
4.86 out of 5 average rating, 7 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
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
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
Home in Old Chatham
Monk's Bunk, Old Chatham
3 bedrooms, 6 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 33 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, 80 reviews
Top guest favourite
Guest house in Stuyvesant
The Falls at Lindenwald Cottage
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 72 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
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
Top guest favourite
Home in Old Chatham
Old Chatham Retreat | Skylight Over the King Bed
2 bedrooms, 2 beds, 2.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Cabin in Chatham
The Upstate Cabin: A secluded getaway in the woods
2 bedrooms, 2 queen beds, 1 bathroom
24–29 Aug
4.97 out of 5 average rating, 158 reviews
Top guest favourite
Barn in Stuyvesant
Pond Side R & R
3 bedrooms, 4 beds, 3.5 bathrooms
17–22 Aug
5.0 out of 5 average rating, 136 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
Cabin in Canaan
Newly Renovated Cabin in the Country
3 bedrooms, 3 beds, 1 bathroom
23–28 Aug
4.96 out of 5 average rating, 192 reviews