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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, 557 reviews
Guest favourite
Place to stay in Ossining
Top#9
1 bedroom, 1 queen bed
15–20 Sept
4.94 out of 5 average rating, 31 reviews
Top guest favourite
Room in Ossining
The hidden gem
1 king bed
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
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
13–18 Sept
5.0 out of 5 average rating, 52 reviews
Top guest favourite
Home in Valhalla
Valhalla Home
2 bedrooms, 3 beds
8–13 Sept
5.0 out of 5 average rating, 32 reviews
Home in Croton-on-Hudson
Croton Country House
4 bedrooms, 4 beds
8–13 Sept
Top guest favourite
Cottage in Cortlandt
The Little Cottage in the Woods
1 bedroom
3–8 Nov
5.0 out of 5 average rating, 229 reviews
Top guest favourite
Home in Putnam Valley
Luxury Lake House Sauna 1h From NYC
2 bedrooms, 3 beds
7–12 Sept
4.99 out of 5 average rating, 190 reviews
Top guest favourite
Home in Piermont
Piermont Getaway Mt. Village Home. 30 min to NYC
2 bedrooms, 3 queen beds
14–19 Nov
4.96 out of 5 average rating, 134 reviews
Top guest favourite
Home in Yorktown Heights
Cozy getaway 1 hr from NYC!
3 bedrooms, 4 beds
6–11 Sept
4.91 out of 5 average rating, 185 reviews
Guest favourite
Townhouse in White Plains
Stylish 4bed 2bath Home in White Plains
4 bedrooms, 4 beds
27 Sept – 2 Oct
4.94 out of 5 average rating, 126 reviews
Guest favourite
Home in Croton-on-Hudson
Croton Calm Retreat w/ hot tub
2 bedrooms, 2 beds
7–12 Sept
4.87 out of 5 average rating, 46 reviews
Top guest favourite
Home in Highland Falls
Billy Joel/JP Morgan Hudson Valley Home 1h to NYC
7 bedrooms, 21 beds
13–18 Sept
5.0 out of 5 average rating, 93 reviews
Top guest favourite
Home in Highland Falls
Spacious, bright 5 bedroom house near West Point
5 bedrooms, 6 beds
20–25 Sept
4.99 out of 5 average rating, 211 reviews
Guest favourite
Home in Suffern
Group Retreat | Pool, Hot Tub & Gourmet Kitchen
4 bedrooms, 13 beds
22–27 Sept
4.91 out of 5 average rating, 54 reviews
Guest favourite
Guest suite in Croton-on-Hudson
The Bluestone - Spacious 2 bedroom w/central air
2 bedrooms, 3 beds
20–25 Sept
4.92 out of 5 average rating, 171 reviews
Top guest favourite
Home in Peekskill
Victorian Eclectic
3 bedrooms, 3 beds
14–19 Sept
4.92 out of 5 average rating, 39 reviews
Guest favourite
Flat in Yonkers
Luxury 3BR • Sleeps 10 • Walk to Metro • Parking
3 bedrooms, 5 beds
27 Sept – 2 Oct
4.92 out of 5 average rating, 52 reviews