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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, 78 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
15–20 Sept
5.0 out of 5 average rating, 53 reviews
Featured hotel
Hotel in White Plains
King
1 bedroom, 1 king bed, 1 bathroom
24–29 Sept
5.0 out of 5 average rating, 7 reviews
Home in Yonkers
Beautiful 2BR jacuzzi & Private Patio
2 bedrooms, 4 beds, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 4 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
Home in Croton-on-Hudson
Croton Country House
4 bedrooms, 4 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Townhouse in White Plains
Stylish 4bed 2bath Home in White Plains
4 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
4.95 out of 5 average rating, 128 reviews
Guest favourite
Home in Suffern
Group Retreat | Pool, Hot Tub & Gourmet Kitchen
4 bedrooms, 13 beds, 3 bathrooms
22–27 Sept
4.91 out of 5 average rating, 55 reviews
Top guest favourite
Home in Philipstown
Gloves Off Retreat • A Quiet Hudson Valley Escape
3 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 8 reviews
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
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, 173 reviews
Top guest favourite
Home in Putnam Valley
Luxury Lake House Sauna 1h From NYC
2 bedrooms, 3 beds, 2 bathrooms
21–26 Sept
4.99 out of 5 average rating, 190 reviews
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
Home in Monroe
Spacious 4BR Retreat | Legoland • Warwick • Trails
5 bedrooms, 7 beds, 2 bathrooms
21–26 Oct
New place to stay
Top guest favourite
Home in Valhalla
Valhalla Home
2 bedrooms, 3 beds, 1 bathroom
28 Sept – 3 Oct
5.0 out of 5 average rating, 33 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