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Search results; Over 1,000 homes in Ossining

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
Guest favourite
Place to stay in Ossining
Top#9
1 bedroom, 1 queen bed, 1 bathroom
27 Sept – 2 Oct
4.94 out of 5 average rating, 31 reviews
Top guest favourite
Room in Ossining
The hidden gem
1 king bed, 1 bathroom
19–24 Sept
4.99 out of 5 average rating, 77 reviews
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
Top guest favourite
Guest suite in Briarcliff Manor
Enjoy Summer Living "Stone Haven" Hudson Valley
1 bedroom, 2 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 52 reviews
Home in Croton-on-Hudson
Croton Country House
4 bedrooms, 4 beds, 2 bathrooms
10–15 Sept
5.0 out of 5 average rating, 3 reviews
Home in Sleepy Hollow
Charming River Town Stay by the Hudson
4 bedrooms, 6 beds, 2 bathrooms
14–19 Sept
New place to stay
Guest favourite
Townhouse in White Plains
Stylish 4bed 2bath Home in White Plains
4 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
4.94 out of 5 average rating, 127 reviews
Top guest favourite
Home in Highland Falls
Spacious, bright 5 bedroom house near West Point
5 bedrooms, 6 beds, 2 bathrooms
20–25 Sept
4.99 out of 5 average rating, 212 reviews
Top guest favourite
Home in Valhalla
Valhalla Home
2 bedrooms, 3 beds, 1 bathroom
9–14 Sept
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Home in Putnam Valley
Luxury Lake House Sauna 1h From NYC
2 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
4.99 out of 5 average rating, 190 reviews
Home in Yonkers
The lucky escape
4 bedrooms, 4 beds, 2 bathrooms
19–24 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Philipstown
Gloves Off Retreat • A Quiet Hudson Valley Escape
3 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Highland Falls
Billy Joel/JP Morgan Hudson Valley Home 1h to NYC
7 bedrooms, 21 beds, 5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 94 reviews
Top guest favourite
Home in Mount Kisco
Incredible barn in country setting
2 bedrooms, 2 beds, 1 bathroom
9–14 Sept
4.94 out of 5 average rating, 160 reviews
Top guest favourite
Home in Peekskill
Victorian Eclectic
3 bedrooms, 3 beds, 1.5 bathrooms
14–19 Sept
4.92 out of 5 average rating, 39 reviews
Top guest favourite
Home in Philipstown
Creekside Home Near Cold Spring & West Point
3 bedrooms, 4 beds, 1 bathroom
26–31 Oct
4.94 out of 5 average rating, 144 reviews
Top guest favourite
Flat in Tarrytown
2 BRs, Easy Walking in Tarrytown and Sleepy Hollow
2 bedrooms, 2 beds, 1 bathroom
19–24 Nov
4.99 out of 5 average rating, 101 reviews
Top guest favourite
Guest house in Elmsford
Private Guest Suite
2 bedrooms, 2 queen beds, 1 bathroom
18–23 Oct
4.98 out of 5 average rating, 41 reviews