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Search results; Over 1,000 homes in Pawling

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Top guest favourite
Home in Pawling
Lakefront retreat
3 bedrooms, 3 beds, 2.5 private bathrooms
20–25 Sept
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5.0 out of 5 average rating, 20 reviews
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Top guest favourite
Guest suite in Pawling
Cozy retreat just a short stroll from the village
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.94 out of 5 average rating, 131 reviews
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Flat in Pawling
Quiet Studio Apartment in Pawling
1 bedroom, 1 king bed, 1 bathroom
30 Oct – 4 Nov
5.0 out of 5 average rating, 155 reviews
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Top guest favourite
Cottage in Pawling
Twin Lakes Designer A-frame Stone Cottage
1 bedroom, 1 queen bed, 1 bathroom
15–20 Nov
4.99 out of 5 average rating, 190 reviews
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Top guest favourite
Home in Pawling
Farmhouse Oasis in the Hudson Valley, Stream Views
4 bedrooms, 6 beds, 3 bathrooms
12–17 Oct
4.97 out of 5 average rating, 108 reviews
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Guest favourite
Cottage in Pawling
Forest Acres Cottage: Appalachian/Empire St Trail!
1 bedroom, 2 beds, 1 bathroom
8–13 Oct
4.97 out of 5 average rating, 116 reviews
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Guest favourite
Home in Pawling
Private Lake House, Retreat
2 bedrooms, 2 beds, 1 bathroom
24–29 Sept
4.94 out of 5 average rating, 34 reviews
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Home in Pawling
Peaceful Farm Stay, Ski Nearby
3 bedrooms, 4 beds, 1.5 bathrooms
1–6 Oct
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Top guest favourite
Home in Pawling
Idyllic Lake Home-Hot tub, Woodstove-Hudson Valley
3 bedrooms, 4 beds, 2 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 13 reviews
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Top guest favourite
Home in Pawling
Quaker Hill Cottage
2 bedrooms, 2 beds, 1.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 15 reviews
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Top guest favourite
Flat in Holmes
Top Side
1 bedroom, 1 bed, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 148 reviews
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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
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Top guest favourite
Home in Holmes
Laurelwood Cottage at Sanita Hill
4 bedrooms, 5 beds, 2 bathrooms
22–27 Sept
5.0 out of 5 average rating, 5 reviews
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Guest favourite
Cabin in Holmes
A View From the Lakehouse
3 bedrooms, 3 beds, 2 bathrooms
18–23 Sept
4.95 out of 5 average rating, 57 reviews
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Top guest favourite
Home in Dover Plains
Somewhere That’s Green, Gameroom/Bar, Fenced yard
3 bedrooms, 4 beds, 2.5 bathrooms
18–23 Sept
5.0 out of 5 average rating, 49 reviews
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Home in Sherman
Private 2-Acre Retreat | Candlewood Beach Access
2 bedrooms, 2 queen beds, 1 bathroom
22–27 Sept
New place to stay
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Top guest favourite
Cabin in Holmes
Spa Cabin with 2 Suites & Hot Tub
5 bedrooms, 7 beds, 3.5 bathrooms
23–28 Sept
4.98 out of 5 average rating, 112 reviews
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Guest favourite
Loft in Sherman
Appalachian Getaway
2 bedrooms, 2 queen beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 21 reviews
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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