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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
31 Aug – 5 Sept
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4.96 out of 5 average rating, 547 reviews
Top guest favourite
Room in Ossining
The hidden gem
1 king bed
4–9 Aug
4.99 out of 5 average rating, 73 reviews
Guest favourite
Place to stay in Ossining
Top#9
1 bedroom, 1 queen bed
29 Aug – 4 Sept
4.93 out of 5 average rating, 30 reviews
Top guest favourite
Guest suite in Briarcliff Manor
Enjoy Summer Living "Stone Haven" Hudson Valley
1 bedroom, 2 beds
23–28 Jul
5.0 out of 5 average rating, 50 reviews
Top guest favourite
Room in Hawthorne
Room: Life is beautiful
2 beds
21–26 Jul
4.89 out of 5 average rating, 122 reviews
Top guest favourite
Room in Croton-on-Hudson
Hudson Valley Stone House Getaway
1 queen bed
30 Aug – 4 Sept
4.98 out of 5 average rating, 542 reviews
Top guest favourite
Cottage in Cortlandt
The Little Cottage in the Woods
1 bedroom
3–8 Aug
5.0 out of 5 average rating, 227 reviews
Home in Briarcliff Manor
Hudson River Views: Briarcliff Manor Home w/ Deck
4 bedrooms, 4 beds
21–26 Jul
Superhost
Room in Ossining
Freshly updated room
1 double bed
11–16 Oct
4.94 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
3–8 Aug
4.92 out of 5 average rating, 167 reviews
Guest favourite
Home in Briarcliff Manor
Hudson River Views: Briarcliff Manor Home w/ Deck
4 bedrooms, 6 beds
21–26 Jul
4.86 out of 5 average rating, 22 reviews
Top guest favourite
Guest house in Woodbury
The Simplicity of the Experience.
1 bedroom, 2 beds
27 Jul – 1 Aug
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Flat in Highland Falls
Riverview B&B 2 Miles to West Point
1 bedroom, 2 beds
30 Jul – 4 Aug
4.99 out of 5 average rating, 193 reviews
Top guest favourite
Chalet in Philipstown
Cozy A-Frame in the Trees · 20 min to WP· 1 hr NYC
3 bedrooms
28 Jul – 2 Aug
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Flat in Croton-on-Hudson
Luxury 2bd⭐Comfort+Style⭐
2 bedrooms, 2 queen beds
3–8 Aug
4.98 out of 5 average rating, 382 reviews
Guest favourite
Home in Haverstraw
Beachfront Home on the Hudson w/ Amazing Views!
1 bedroom, 1 queen bed
1–8 May
4.94 out of 5 average rating, 78 reviews
Top guest favourite
Guest house in Elmsford
Private Guest Suite
2 bedrooms, 2 queen beds
5–10 Aug
5.0 out of 5 average rating, 34 reviews
Top guest favourite
Home in Peekskill
Victorian Eclectic
3 bedrooms, 3 beds
4–9 Aug
4.92 out of 5 average rating, 36 reviews
Top guest favourite
Guest suite in Katonah
Comfy Peaceful Retreat
1 bedroom, 1 queen bed
26–31 Jul
4.92 out of 5 average rating, 157 reviews