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Search results; Over 1,000 homes in Pawling

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Top guest favourite
Guest suite in Pawling
Cozy retreat just a short stroll from the village
1 bedroom, 1 bed, 1 private bathroom
4–9 Oct
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4.94 out of 5 average rating, 131 reviews
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Top guest favourite
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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Top guest favourite
Cottage in Pawling
Twin Lakes Designer A-frame Stone Cottage
1 bedroom, 1 queen bed
15–20 Nov
4.99 out of 5 average rating, 190 reviews
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Guest favourite
Cottage in Pawling
Forest Acres Cottage: Appalachian/Empire St Trail!
1 bedroom, 2 beds
14–19 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
1–6 Oct
4.94 out of 5 average rating, 34 reviews
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Top guest favourite
Home in Pawling
Farmhouse Oasis in the Hudson Valley, Stream Views
4 bedrooms, 6 beds
26–31 Oct
4.97 out of 5 average rating, 108 reviews
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Top guest favourite
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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Top guest favourite
Flat in Holmes
Top Side
1 bedroom, 1 bed
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
20–25 Oct
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
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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Top guest favourite
Home in Holmes
Laurelwood Cottage at Sanita Hill
4 bedrooms, 5 beds
19–24 Oct
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
4–9 Oct
4.95 out of 5 average rating, 58 reviews
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Top guest favourite
Home in Pawling
Quaker Hill Cottage
2 bedrooms, 2 beds
1–6 Oct
5.0 out of 5 average rating, 15 reviews
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Guest favourite
Cottage in Sherman
Candlewood Cottage
2 bedrooms, 4 beds
12–17 Oct
5.0 out of 5 average rating, 7 reviews
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Home in Sherman
Private 2-Acre Retreat | Candlewood Beach Access
2 bedrooms, 2 queen beds
24–29 Oct
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Top guest favourite
Home in Dover Plains
Somewhere That’s Green, Gameroom/Bar, Fenced yard
3 bedrooms, 4 beds
1–6 Oct
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
11–16 Nov
4.96 out of 5 average rating, 105 reviews
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Top guest favourite
Barn in Dover Plains
Punto Pino Farm Stay
1 bedroom, 2 beds
11–16 Oct
5.0 out of 5 average rating, 14 reviews
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Guest favourite
Loft in Sherman
Appalachian Getaway
2 bedrooms, 2 queen beds
1–6 Oct
5.0 out of 5 average rating, 21 reviews