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Search results; Over 1,000 homes in Ossining

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Guest favourite
Home in Ossining
Lower Hudson Valley Idyllic Retreat
4 bedrooms, 5 beds, 2.5 private bathrooms
9–14 Nov
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4.84 out of 5 average rating, 170 reviews
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Top guest favourite
Flat in Ossining
Hudson River Peaceful Getaway, Explore from here
2 bedrooms, 2 beds, 1 bathroom
15–20 Nov
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, 1 bathroom
11–16 Oct
4.99 out of 5 average rating, 79 reviews
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Top guest favourite
Home in Ossining
Hudson Valley Fall Escape · 50min to NYC · 3 Acre
3 bedrooms, 4 beds, 1.5 bathrooms
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, 1 bathroom
18–23 Oct
5.0 out of 5 average rating, 54 reviews
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Home in Briarcliff Manor
Hudson River Views: Briarcliff Manor Home w/ Deck
4 bedrooms, 4 beds, 6 bathrooms
28 Nov – 3 Dec
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Guest favourite
Home in Haverstraw
Beachfront Home on the Hudson w/ Amazing Views!
1 bedroom, 1 queen bed, 1 bathroom
1–8 May
4.94 out of 5 average rating, 80 reviews
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Guest favourite
Guest suite in Croton-on-Hudson
The Bluestone - Spacious 2 bedroom w/central air
2 bedrooms, 3 beds, 1 bathroom
10–15 Oct
4.93 out of 5 average rating, 174 reviews
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Top guest favourite
Guest suite in Pleasantville
Serene Escape | Private Suite | Ideal for 2
1 bedroom, 1 queen bed, 1 bathroom
8–13 Oct
5.0 out of 5 average rating, 8 reviews
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Guest favourite
Room in Ossining
1 private room with shared bath
1 double bed, 1 bathroom
1–6 May
5.0 out of 5 average rating, 7 reviews
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Guest favourite
Home in Briarcliff Manor
Hudson River Views: Briarcliff Manor Home w/ Deck
4 bedrooms, 6 beds, 6 bathrooms
28 Nov – 3 Dec
4.88 out of 5 average rating, 24 reviews
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Top guest favourite
Flat in Croton-on-Hudson
Croton Nook - Cozy Getaway
2 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 36 reviews
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Home in Croton-on-Hudson
Croton Country House
4 bedrooms, 4 beds, 2 bathrooms
22–27 Sept
5.0 out of 5 average rating, 3 reviews
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Superhost
Room in Tarrytown
Tarrytown Room with Deck Steps from Main Street
1 queen bed, 1 bathroom
1–6 Dec
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Peekskill
Victorian Eclectic
3 bedrooms, 3 beds, 1.5 bathrooms
18–23 Oct
4.93 out of 5 average rating, 40 reviews
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Guest favourite
Barn in Katonah
Red Barn/Heated Salt Pool and Cedar Soaking Tub
3 beds, 1 bathroom
20–25 Sept
4.96 out of 5 average rating, 146 reviews
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Guest favourite
Home in Nyack
Updated Victorian in the heart of Nyack
3 bedrooms, 3 beds, 2.5 bathrooms
1–6 Apr
5.0 out of 5 average rating, 8 reviews
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Top guest favourite
Guest house in Tomkins Cove
The cottage at Oasis Cove
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.89 out of 5 average rating, 38 reviews
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Top guest favourite
Home in Philipstown
Gloves Off Retreat • A Quiet Hudson Valley Escape
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 8 reviews