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Search results; Over 1,000 homes in Pawling

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Guest favourite
Cottage in Pawling
Forest Acres Cottage: Appalachian/Empire St Trail!
1 bedroom, 2 beds, 1 private bathroom
14–19 Oct
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4.97 out of 5 average rating, 116 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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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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Home in Pawling
Farmhouse Oasis in the Hudson Valley, Stream Views
4 bedrooms, 6 beds, 3 bathrooms
26–31 Oct
4.97 out of 5 average rating, 108 reviews
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Guest favourite
Home in Pawling
Private Lake House, Retreat
2 bedrooms, 2 beds, 1 bathroom
1–6 Oct
4.94 out of 5 average rating, 34 reviews
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Home in Pawling
Lakefront retreat
3 bedrooms, 3 queen beds, 2.5 bathrooms
19–24 Oct
5.0 out of 5 average rating, 20 reviews
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Flat in Holmes
Top Side
1 bedroom, 1 bed, 1 bathroom
15–20 Nov
5.0 out of 5 average rating, 150 reviews
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Top guest favourite
Home in Pawling
Idyllic Lake Home-Hot tub, Woodstove-Hudson Valley
3 bedrooms, 4 beds, 2 bathrooms
20–25 Oct
5.0 out of 5 average rating, 14 reviews
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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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Home in Holmes
Laurelwood Cottage at Sanita Hill
4 bedrooms, 5 beds, 2 bathrooms
19–24 Oct
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Home in Pawling
Quaker Hill Cottage
2 bedrooms, 2 beds, 1.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 15 reviews
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Home in Sherman
Private 2-Acre Retreat | Candlewood Beach Access
2 bedrooms, 2 queen beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Cabin in Holmes
A View From the Lakehouse
3 bedrooms, 3 beds, 2 bathrooms
4–9 Oct
4.95 out of 5 average rating, 58 reviews
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Guest favourite
Cottage in Sherman
Candlewood Cottage
2 bedrooms, 4 beds, 1 bathroom
12–17 Oct
5.0 out of 5 average rating, 7 reviews
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Home in Dover Plains
Somewhere That’s Green, Gameroom/Bar, Fenced yard
3 bedrooms, 4 beds, 2.5 bathrooms
27 Oct – 1 Nov
5.0 out of 5 average rating, 49 reviews
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Top guest favourite
Home in Dover Plains
Hillside Grove
4 bedrooms, 5 beds, 2 bathrooms
11–16 Nov
4.96 out of 5 average rating, 105 reviews
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Barn in Dover Plains
Punto Pino Farm Stay
1 bedroom, 2 beds, 1 bathroom
11–16 Oct
5.0 out of 5 average rating, 14 reviews
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Home in Sherman
Slice of Paradise in the Country
2 bedrooms, 2 beds, 2 bathrooms
31 Oct – 5 Nov
5.0 out of 5 average rating, 110 reviews
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Guest favourite
Loft in Sherman
Appalachian Getaway
2 bedrooms, 2 queen beds, 1 bathroom
20–25 Oct
5.0 out of 5 average rating, 21 reviews