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Search results; Over 1,000 homes in Ossining

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Top guest favourite
Flat in Ossining
Hudson River Peaceful Getaway, Explore from here
2 bedrooms, 2 beds, 1 private bathroom
15–20 Nov
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4.96 out of 5 average rating, 559 reviews
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Top guest favourite
Room in Ossining
The hidden gem
1 king bed
11–16 Oct
4.99 out of 5 average rating, 79 reviews
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Flat in Nyack
Stylish Nyack 1BR | King Bed + Parking
1 bedroom, 1 king bed
1–6 Oct
New place to stay
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Top guest favourite
Home in Ossining
Hudson Valley Fall Escape · 50min to NYC · 3 Acre
3 bedrooms, 4 beds
15–22 Nov
5.0 out of 5 average rating, 20 reviews
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Top guest favourite
Guest suite in Briarcliff Manor
Enjoy Summer Living "Stone Haven" Hudson Valley
1 bedroom, 2 beds
18–23 Oct
5.0 out of 5 average rating, 54 reviews
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Guest favourite
Home in Nyack
Updated Victorian in the heart of Nyack
3 bedrooms, 3 beds
1–6 Apr
5.0 out of 5 average rating, 8 reviews
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Home in Croton-on-Hudson
Croton Country House
4 bedrooms, 4 beds
26–31 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Villa in Stony Point
Spacious 10BR Escape w/Pool, Hot Tub & Game Room
10 bedrooms, 15 beds
1–6 Oct
5.0 out of 5 average rating, 5 reviews
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Home in Stony Point
Massive 10BR Estate w/Pool, Hot Tub & Pizza Oven
10 bedrooms, 25 beds
1–6 Oct
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Guest suite in Pleasantville
Serene Escape | Private Suite | Ideal for 2
1 bedroom, 1 queen bed
8–13 Oct
5.0 out of 5 average rating, 8 reviews
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Top guest favourite
Home in Highland Falls
Spacious, bright 5 bedroom house near West Point
5 bedrooms, 6 beds
18–23 Oct
4.99 out of 5 average rating, 214 reviews
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Guest favourite
Townhouse in White Plains
Charming 3BR Home - Quiet Stay, Close to NYC
3 bedrooms, 4 beds
11–16 Oct
4.95 out of 5 average rating, 143 reviews
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Guest favourite
Flat in Yonkers
Spacious 3BR Terracotta Retreat with Free Parking!
3 bedrooms, 3 beds
1–6 Nov
4.92 out of 5 average rating, 97 reviews
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Superhost
Room in Ossining
Freshly updated room
1 double bed
8–13 Dec
4.94 out of 5 average rating, 32 reviews
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Top guest favourite
Home in Philipstown
Gloves Off Retreat • A Quiet Hudson Valley Escape
3 bedrooms, 3 beds
17–22 Oct
5.0 out of 5 average rating, 8 reviews
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Top guest favourite
Home in Valhalla
Valhalla Home
2 bedrooms, 3 beds
1–6 Oct
5.0 out of 5 average rating, 34 reviews
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Top guest favourite
Home in Highland Falls
Billy Joel/JP Morgan Hudson Valley Home 1h to NYC
7 bedrooms, 21 beds
1–6 Oct
5.0 out of 5 average rating, 95 reviews
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Guest favourite
Home in Orangeburg
Matt’s Cozy Quarters Near NYC w/Outdoor Living
3 bedrooms, 6 beds
22–27 Dec
4.8 out of 5 average rating, 15 reviews
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Flat in Cold Spring
Charming Main st Stay with breakfast
1 queen bed
18–23 Oct
New place to stay