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Search results; Over 1,000 homes in Pawling

Top guest favourite
Cottage in Pawling
Twin Lakes Designer A-frame Stone Cottage
1 bedroom, 1 bed, 1 private bathroom
27 Sept – 2 Oct
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4.99 out of 5 average rating, 184 reviews
Top guest favourite
Flat in Pawling
Quiet Studio Apartment in Pawling
1 bedroom, 1 king bed, 1 bathroom
9–14 Oct
5.0 out of 5 average rating, 150 reviews
Guest favourite
Home in Pawling
Private Lake House, Retreat
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
4.94 out of 5 average rating, 31 reviews
Home in Pawling
Quaker Hill Hideway | 7 Acres, Pool & Stargazing
3 bedrooms, 3 beds, 2.5 bathrooms
12–17 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Cottage in Pawling
Forest Acres Cottage: Appalachian/Empire St Trail!
1 bedroom, 2 beds, 1 bathroom
4–9 Sept
4.97 out of 5 average rating, 113 reviews
Top guest favourite
Home in Pawling
Lakefront retreat
3 bedrooms, 3 queen beds, 2.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Flat in Holmes
Top Side
1 bedroom, 1 bed, 1 bathroom
24–29 Oct
5.0 out of 5 average rating, 142 reviews
Top guest favourite
Home in Pawling
Historic Mansion: 6BR Retreat + Horse Sanctuary
6 bedrooms, 8 beds, 4 bathrooms
13–18 Oct
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Pawling
Quaker Hill Cottage
2 bedrooms, 2 beds, 1.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Pawling
Idyllic Lake Home-Hot tub, Woodstove-Hudson Valley
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 11 reviews
Home in Holmes
Laurelwood Cottage at Sanita Hill
4 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
Top guest favourite
Guest house in Southbury
The Perch in the Purchase
1 bedroom, 2 beds, 1 bathroom
8–13 Nov
5.0 out of 5 average rating, 73 reviews
Top guest favourite
Home in Dover Plains
Somewhere That’s Green, Gameroom/Bar, Fenced yard
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Camper van/Motorhome in Wassaic
Glamp in a 1970s Airstream | Hot Tub | NYC Train
3 beds, 1 bathroom
6–11 Sept
4.99 out of 5 average rating, 99 reviews
Top guest favourite
Cottage in Brewster
Lakefront Brewster Vacation Rental w/ Private Dock
3 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
4.98 out of 5 average rating, 51 reviews
Top guest favourite
Cabin in Carmel Hamlet
Cozy Log Cabin Getaway
2 bedrooms, 4 beds, 1.5 bathrooms
4–9 Oct
4.97 out of 5 average rating, 95 reviews
Top guest favourite
Loft in Sherman
Appalachian Getaway
2 bedrooms, 2 queen beds, 1 bathroom
25–30 Sept
5.0 out of 5 average rating, 20 reviews
Home in Washington
The Flirt | Restored 1927 Lake Waramaug Cottage
2 bedrooms, 2 beds, 1.5 bathrooms
1–6 Sept
New place to stay
Top guest favourite
Home in Fishkill Village
Hudson Valley Retreat w/ Sauna Near Beacon sleeps7
3 bedrooms, 4 beds, 2 bathrooms
29 Oct – 3 Nov
5.0 out of 5 average rating, 82 reviews