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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
21–26 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, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 150 reviews
Top guest favourite
Cottage in Pawling
Twin Lakes Designer A-frame Stone Cottage
1 bedroom, 1 queen bed, 1 bathroom
27 Sept – 2 Oct
4.99 out of 5 average rating, 183 reviews
Guest favourite
Cottage in Pawling
Forest Acres Cottage: Appalachian/Empire St Trail!
1 bedroom, 2 beds, 1 bathroom
19–24 Aug
4.97 out of 5 average rating, 113 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
Home in Pawling
Private Lake House, Retreat
2 bedrooms, 2 beds, 1 bathroom
30 Aug – 4 Sept
4.94 out of 5 average rating, 31 reviews
Top guest favourite
Flat in Holmes
Top Side
1 bedroom, 1 bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 142 reviews
Top guest favourite
Home in Pawling
Country Village Getaway
2 bedrooms, 2 queen beds, 1.5 bathrooms
1–7 Jun
4.93 out of 5 average rating, 40 reviews
Top guest favourite
Home in Pawling
Quaker Hill Cottage
2 bedrooms, 2 beds, 1.5 bathrooms
25–30 Aug
5.0 out of 5 average rating, 13 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
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
Home in New Milford
Cozy cottage
1 bedroom, 1 queen bed, 1 bathroom
21–26 Sept
5.0 out of 5 average rating, 41 reviews
Top guest favourite
Barn in Roxbury
Fully Renovated Rural Barn
1 bedroom, 2 beds, 1.5 bathrooms
29 Oct – 3 Nov
5.0 out of 5 average rating, 108 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, 10 reviews
Home in Holmes
Laurelwood Cottage at Sanita Hill
4 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
Guest favourite
Dome in Dover Plains
Architect-Designed Dome on Private 7-Acre Retreat
1 bedroom, 2 beds, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Room in Hyde Park
Scandinavian Designed Euro Room - 1 of 3 rooms
1 queen bed, 1 bathroom
6–11 Sept
4.96 out of 5 average rating, 533 reviews
Guest favourite
Room in Brewster
The Dandelion Room -On 127 Acres
1 double bed, 1 bathroom
6–11 Sept
4.92 out of 5 average rating, 37 reviews
Top guest favourite
Guest house in Southbury
The Perch in the Purchase
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 73 reviews