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Search results; Over 1,000 homes in Pleasant Valley

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Top guest favourite
Cabin in Pleasant Valley
Secluded Mountaintop Getaway near Poughkeepsie
2 bedrooms, 3 beds, 1 private bathroom
28 Sept – 3 Oct
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4.99 out of 5 average rating, 77 reviews
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Top guest favourite
Loft in Pleasant Valley
Be our guest at The Nest!
1 king bed, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 61 reviews
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Home in Pleasant Valley
Relaxing Lodge Retreat
6 bedrooms, 7 beds, 3.5 bathrooms
8–13 Sept
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Guest favourite
Room in Poughkeepsie
Twin bed , WIFI, basement single room 7
1 single bed, 1 bathroom
2–7 Sept
4.94 out of 5 average rating, 31 reviews
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Top guest favourite
Home in Poughkeepsie
Beautiful, Fun, Spacious 5 Acre Family Retreat
3 bedrooms, 7 beds, 2.5 bathrooms
20–25 Sept
4.93 out of 5 average rating, 114 reviews
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Guest favourite
Home in Pleasant Valley
Black Oak Estate. Your Luxurious Sanctuary Awaits
4 bedrooms, 7 beds, 2.5 bathrooms
29 Oct – 3 Nov
5.0 out of 5 average rating, 6 reviews
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Superhost
Shared room in Poughkeepsie
Tiny space double bed corner privacy screen #6
1 bedroom, 1 bed, 2 shared bathrooms
1–6 Sept
5.0 out of 5 average rating, 33 reviews
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Superhost
Home in Hyde Park
Wooded Rhinebeck-Beacon area Escape w/Outdoor Spa
2 bedrooms, 4 beds, 2.5 bathrooms
1–6 Sept
4.99 out of 5 average rating, 85 reviews
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Top guest favourite
Room in Poughkeepsie
Hudson Pond · Hideaway King Suite · GF Breakfast
1 king bed, 1 bathroom
19–25 Oct
4.96 out of 5 average rating, 246 reviews
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Home in Hyde Park
Luxe Mountain Getaway on Private Rd Near Rhinebeck
3 bedrooms, 5 beds, 3.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 4 reviews
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Superhost
Home in Hyde Park
Charming Hyde Park Retreat|Minutes from Vanderbilt
3 bedrooms, 3 queen beds, 1.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 35 reviews
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Top guest favourite
Home in Highland
VIEWS on Hudson River / Luxury Modern Home
4 bedrooms, 5 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 8 reviews
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Top guest favourite
Cottage in Hyde Park
Cozy Historic Hyde Park Cottage - Near CIA & River
3 bedrooms, 3 beds, 1.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 15 reviews
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Superhost
Home in Staatsburg
The Daydream: Hudson River Views, 4 bedrooms & Gym
4 bedrooms, 5 beds, 3.5 bathrooms
2–7 Oct
4.99 out of 5 average rating, 99 reviews
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Guest favourite
Shared room in Poughkeepsie
Literal bargain basement space #9
1 bedroom, 1 bed, 1.5 shared bathrooms
1–6 Sept
4.96 out of 5 average rating, 53 reviews
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Top guest favourite
Flat in Poughkeepsie
Fully Renovated Loft Apartment Permit # 20240329
2 bedrooms, 2 beds, 1.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 35 reviews
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Guest favourite
Home in Ulster Park
The Valley House
6 bedrooms, 6 beds, 1.5 bathrooms
9–14 Sept
5.0 out of 5 average rating, 8 reviews
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Guest favourite
Home in Millbrook
Woodstock Cove - Your Cozy Oasis Awaits!
4 bedrooms, 5 beds, 3 bathrooms
8–13 Sept
5.0 out of 5 average rating, 6 reviews
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Guest favourite
Barn in Dover Plains
Punto Pino Farm Stay
1 bedroom, 2 beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 9 reviews