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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, 1 bathroom
15–20 Sept
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
Home in Sleepy Hollow
Charming River Town Stay by the Hudson
4 bedrooms, 6 beds, 2 bathrooms
5–10 Sept
New place to stay
Featured hotel
Room in White Plains
King
1 king bed, 1 bathroom
10–15 Sept
5.0 out of 5 average rating, 5 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
Flat in Sleepy Hollow
Large 3BR Sleepy Hollow Apt, Walk to Legend Sites
3 bedrooms, 4 beds, 2 bathrooms
11–16 Sept
5.0 out of 5 average rating, 3 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 Putnam Valley
Luxury Lake House Sauna 1h From NYC
2 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
4.99 out of 5 average rating, 190 reviews
Top guest favourite
Home in Valhalla
Valhalla Home
2 bedrooms, 3 beds, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 32 reviews
Guest favourite
Guest suite in Croton-on-Hudson
The Bluestone - Spacious 2 bedroom w/central air
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
4.92 out of 5 average rating, 171 reviews
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, 126 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
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
Guest favourite
Room in Hawthorne
Room: Life is beautiful
2 beds, 1 bathroom
7–12 Sept
4.89 out of 5 average rating, 124 reviews
Top guest favourite
Flat in Croton-on-Hudson
Croton Nook - Cozy Getaway
2 beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 34 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