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Search results; Over 1,000 homes in Pawling

Top guest favourite
Guest suite in Pawling
Cozy retreat just a short stroll from the village
1 bedroom, 1 bed, 1 private bathroom
14–19 Aug
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4.94 out of 5 average rating, 130 reviews
Top guest favourite
Flat in Pawling
Quiet Studio Apartment in Pawling
1 bedroom, 1 king bed
23–28 Aug
5.0 out of 5 average rating, 148 reviews
Top guest favourite
Cottage in Pawling
Twin Lakes Designer A-frame Stone Cottage
1 bedroom, 1 queen bed
24–29 Aug
4.99 out of 5 average rating, 181 reviews
Guest favourite
Cottage in Pawling
Forest Acres Cottage: Appalachian/Empire St Trail!
1 bedroom, 2 beds
18–23 Aug
4.97 out of 5 average rating, 113 reviews
Guest favourite
Home in Pawling
Private Lake House, Retreat
2 bedrooms, 2 beds
27 Aug – 1 Sept
4.93 out of 5 average rating, 30 reviews
Home in Pawling
Quaker Hill Hideway | 7 Acres, Pool & Stargazing
3 bedrooms, 3 beds
8–13 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Pawling
Lakefront retreat
3 bedrooms, 3 queen beds
8–13 Sept
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Flat in Holmes
Top Side
1 bedroom, 1 bed
20–25 Sept
5.0 out of 5 average rating, 140 reviews
Home in Holmes
Laurelwood Cottage at Sanita Hill
4 bedrooms, 5 beds
13–18 Aug
Top guest favourite
Home in Pawling
Quaker Hill Cottage
2 bedrooms, 2 beds
25–30 Aug
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
8–13 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Pawling
Historic Mansion: 6BR Retreat + Horse Sanctuary
6 bedrooms, 8 beds
13–18 Oct
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Cabin in New Milford
Stylish & Scenic Escape: Chef's Kitchen ~ Hot Tub
3 bedrooms, 4 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 111 reviews
Top guest favourite
Home in Pawling
Country Village Getaway
2 bedrooms, 2 queen beds
1–7 Jun
4.93 out of 5 average rating, 40 reviews
Top guest favourite
Camper van/Motorhome in Wassaic
Glamp in a 1970s Airstream | Hot Tub | NYC Train
3 beds
6–11 Sept
4.99 out of 5 average rating, 96 reviews
Guest favourite
Dome in Dover Plains
Architect-Designed Dome on Private 7-Acre Retreat
1 bedroom, 2 beds
24–29 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in New Fairfield
Beautiful Lakefront Retreat with Private Dock
3 bedrooms, 4 beds
9–15 Oct
4.93 out of 5 average rating, 132 reviews
Top guest favourite
Home in Dover Plains
Somewhere That’s Green, Gameroom/Bar, Fenced yard
3 bedrooms, 4 beds
21–26 Aug
5.0 out of 5 average rating, 48 reviews
Top guest favourite
Barn in Roxbury
Fully Renovated Rural Barn
1 bedroom, 2 beds
12–17 Sept
5.0 out of 5 average rating, 106 reviews