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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
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
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
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
17–22 Sept
5.0 out of 5 average rating, 54 reviews
Home in Sleepy Hollow
Charming River Town Stay by the Hudson
4 bedrooms, 6 beds
9–14 Nov
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
27 Sept – 2 Oct
4.95 out of 5 average rating, 129 reviews
Home in Croton-on-Hudson
Croton Country House
4 bedrooms, 4 beds
17–22 Sept
5.0 out of 5 average rating, 3 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, 213 reviews
Guest favourite
Home in Nyack
Updated Victorian in the heart of Nyack
3 bedrooms, 3 beds
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
20–25 Sept
4.93 out of 5 average rating, 174 reviews
Top guest favourite
Home in Mount Kisco
Incredible barn in country setting
2 bedrooms, 2 beds
16–21 Sept
4.94 out of 5 average rating, 160 reviews
Guest favourite
Home in Putnam Valley
Lakefront Cedar Sauna | Dock | Balcony Over Water
3 bedrooms, 3 beds
30 Sept – 5 Oct
5.0 out of 5 average rating, 7 reviews
Home in Briarcliff Manor
Hudson River Views: Briarcliff Manor Home w/ Deck
4 bedrooms, 4 beds
28 Nov – 3 Dec
Home in Monroe
Spacious 4BR Retreat | Legoland • Warwick • Trails
5 bedrooms, 7 beds
21–26 Oct
New place to stay
Top guest favourite
Flat in Tarrytown
2 BRs, Easy Walking in Tarrytown and Sleepy Hollow
2 bedrooms, 2 beds
19–24 Nov
4.99 out of 5 average rating, 103 reviews
Top guest favourite
Home in Peekskill
Victorian Eclectic
3 bedrooms, 3 beds
21–26 Sept
4.92 out of 5 average rating, 39 reviews
Guest favourite
Room in Ossining
1 private room with shared bath
1 double bed
1–6 May
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Highland Falls
Billy Joel/JP Morgan Hudson Valley Home 1h to NYC
7 bedrooms, 21 beds
25–30 Sept
5.0 out of 5 average rating, 95 reviews