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Search results; Over 1,000 homes in Ossining

Superhost
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, 168 reviews
Guest favourite
Place to stay in Ossining
Top#9
1 bedroom, 1 queen bed, 1 bathroom
15–20 Sept
4.94 out of 5 average rating, 31 reviews
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, 557 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
Featured hotel
Room in White Plains
King
1 king bed, 1 bathroom
3–8 Sept
5.0 out of 5 average rating, 5 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, 19 reviews
Flat in Sleepy Hollow
Large 3BR Sleepy Hollow Apt, Walk to Legend Sites
3 bedrooms, 4 beds, 2 bathrooms
3–8 Sept
5.0 out of 5 average rating, 3 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
8–13 Sept
Top guest favourite
Home in Piermont
Piermont Getaway Mt. Village Home. 30 min to NYC
2 bedrooms, 3 queen beds, 1.5 bathrooms
14–19 Nov
4.96 out of 5 average rating, 134 reviews
Top guest favourite
Home in Valhalla
Valhalla Home
2 bedrooms, 3 beds, 1 bathroom
4–9 Sept
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Cottage in Cortlandt
The Little Cottage in the Woods
1 bedroom, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 229 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
Spacious, bright 5 bedroom house near West Point
5 bedrooms, 6 beds, 2 bathrooms
20–25 Sept
4.99 out of 5 average rating, 211 reviews
Top guest favourite
Home in Yorktown Heights
Cozy getaway 1 hr from NYC!
3 bedrooms, 4 beds, 3 bathrooms
6–11 Sept
4.91 out of 5 average rating, 185 reviews
Top guest favourite
Home in Mount Kisco
Incredible barn in country setting
2 bedrooms, 2 beds, 1 bathroom
4–9 Sept
4.94 out of 5 average rating, 160 reviews
Guest favourite
Home in Suffern
Group Retreat | Pool, Hot Tub & Gourmet Kitchen
4 bedrooms, 13 beds, 3 bathrooms
7–12 Sept
4.91 out of 5 average rating, 54 reviews
Top guest favourite
Room in Elmsford
Quiet room in the heart of Westchester
1 single bed, 1 bathroom
27 Sept – 2 Oct
4.97 out of 5 average rating, 116 reviews
Guest favourite
Home in Croton-on-Hudson
Croton Calm Retreat w/ hot tub
2 bedrooms, 2 beds, 1.5 bathrooms
7–12 Sept
4.87 out of 5 average rating, 46 reviews