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Search results; Over 1,000 homes in Pawling

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Top guest favourite
Cottage in Pawling
Twin Lakes Designer A-frame Stone Cottage
1 bedroom, 1 bed, 1 private bathroom
15–20 Nov
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4.99 out of 5 average rating, 190 reviews
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Flat in Pawling
Quiet Studio Apartment in Pawling
1 bedroom, 1 king bed
30 Oct – 4 Nov
5.0 out of 5 average rating, 155 reviews
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Guest suite in Pawling
Cozy retreat just a short stroll from the village
1 bedroom, 1 queen bed
4–9 Oct
4.94 out of 5 average rating, 131 reviews
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Home in Pawling
Farmhouse Oasis in the Hudson Valley, Stream Views
4 bedrooms, 6 beds
12–17 Oct
4.97 out of 5 average rating, 108 reviews
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Cottage in Pawling
Forest Acres Cottage: Appalachian/Empire St Trail!
1 bedroom, 2 beds
12–17 Oct
4.97 out of 5 average rating, 116 reviews
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Home in Pawling
Lakefront retreat
3 bedrooms, 3 queen beds
19–24 Oct
5.0 out of 5 average rating, 20 reviews
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Home in Pawling
Private Lake House, Retreat
2 bedrooms, 2 beds
24–29 Sept
4.94 out of 5 average rating, 34 reviews
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Home in Pawling
Country Village Getaway
2 bedrooms, 2 queen beds
1–7 Jun
4.93 out of 5 average rating, 40 reviews
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Home in Holmes
Laurelwood Cottage at Sanita Hill
4 bedrooms, 5 beds
22–27 Sept
5.0 out of 5 average rating, 5 reviews
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Home in Pawling
Idyllic Lake Home-Hot tub, Woodstove-Hudson Valley
3 bedrooms, 4 beds
20–25 Oct
5.0 out of 5 average rating, 13 reviews
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Home in Dover Plains
Somewhere That’s Green, Gameroom/Bar, Fenced yard
3 bedrooms, 4 beds
29 Sept – 4 Oct
5.0 out of 5 average rating, 49 reviews
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Cabin in Holmes
Spa Cabin with 2 Suites & Hot Tub
5 bedrooms, 7 beds
23–28 Sept
4.98 out of 5 average rating, 112 reviews
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Home in Sherman
Private 2-Acre Retreat | Candlewood Beach Access
2 bedrooms, 2 queen beds
22–27 Sept
New place to stay
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Home in Redding
Retreat with Heated Pool, 1 Mile to NYC Train
4 bedrooms, 5 beds
4–9 Oct
4.99 out of 5 average rating, 109 reviews
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Guest favourite
Flat in Danbury
Hat City Danbury II | Welcome to your Retreat
2 bedrooms, 2 beds
21–26 Sept
4.96 out of 5 average rating, 24 reviews
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Flat in Holmes
Top Side
1 bedroom, 1 bed
25–30 Oct
5.0 out of 5 average rating, 148 reviews
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Flat in Danbury
Lakeview Suite Pet friendly Hot Tub 4 Park Spots
3 bedrooms, 5 beds
20–25 Sept
5.0 out of 5 average rating, 32 reviews
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Guest favourite
Cabin in Holmes
A View From the Lakehouse
3 bedrooms, 3 beds
21–26 Sept
4.95 out of 5 average rating, 58 reviews
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Cottage in Brewster
Lakefront Brewster Vacation Rental w/ Private Dock
3 bedrooms, 4 beds
21–26 Sept
4.98 out of 5 average rating, 54 reviews