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Search results; Over 1,000 homes in Pawling

Guest favourite
Home in Pawling
Farmhouse Oasis in the Hudson Valley, Stream Views
4 bedrooms, 6 beds, 3 private bathrooms
23–28 Aug
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4.97 out of 5 average rating, 105 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, 184 reviews
Guest favourite
Cottage in Pawling
Forest Acres Cottage: Appalachian/Empire St Trail!
1 bedroom, 2 beds, 1 bathroom
20–25 Aug
4.97 out of 5 average rating, 113 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
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
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
20–25 Sept
5.0 out of 5 average rating, 142 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
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
25–30 Aug
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Dover Plains
Somewhere That’s Green, Gameroom/Bar, Fenced yard
3 bedrooms, 4 beds, 2.5 bathrooms
21–26 Aug
5.0 out of 5 average rating, 49 reviews
Home in Holmes
Laurelwood Cottage at Sanita Hill
4 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
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
Home in New Fairfield
Beautiful Lakefront Retreat with Private Dock
3 bedrooms, 4 beds, 2.5 bathrooms
9–15 Oct
4.93 out of 5 average rating, 132 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
Guest suite in Sherman
Cozy Scenic New England rural retreat hike & kayak
3 beds, 1 bathroom
6–11 Sept
4.96 out of 5 average rating, 190 reviews
Home in Dover Plains
Luxury Newly Renovated 3BR 2BA| Family Fun
3 bedrooms, 1 queen bed, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Dover Plains
Blue Heron - Scenic Oasis on Working Farm
3 bedrooms, 4 beds, 2 bathrooms
25–30 Aug
5.0 out of 5 average rating, 48 reviews