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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
23–28 Aug
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4.84 out of 5 average rating, 166 reviews
Top guest favourite
Flat in Ossining
Hudson River Peaceful Getaway, Explore from here
2 bedrooms, 2 beds, 1 bathroom
31 Aug – 5 Sept
4.96 out of 5 average rating, 546 reviews
Top guest favourite
Room in Ossining
The hidden gem
1 king bed, 1 bathroom
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, 1 bathroom
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, 1 bathroom
22–27 Jul
5.0 out of 5 average rating, 50 reviews
Top guest favourite
Room in Hawthorne
Room: Life is beautiful
2 beds, 1 bathroom
20–25 Jul
4.88 out of 5 average rating, 121 reviews
Top guest favourite
Room in Croton-on-Hudson
Hudson Valley Stone House Getaway
1 queen bed, 1 bathroom
30 Aug – 4 Sept
4.98 out of 5 average rating, 542 reviews
Guest suite in Pleasantville
Serene Escape | Private Suite | Ideal for 2
1 bedroom, 1 queen bed, 1 bathroom
25–30 Jul
5.0 out of 5 average rating, 4 reviews
Guest favourite
Guest suite in Croton-on-Hudson
The Bluestone - Spacious 2 bedroom w/central air
2 bedrooms, 3 beds, 1 bathroom
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, 6 bathrooms
20–25 Jul
4.86 out of 5 average rating, 22 reviews
Top guest favourite
Flat in Highland Falls
Riverview B&B 2 Miles to West Point
1 bedroom, 2 beds, 1 bathroom
30 Jul – 4 Aug
4.99 out of 5 average rating, 193 reviews
Top guest favourite
Home in Piermont
Piermont's Getaway Mt. Village Home. 30min to NYC
2 bedrooms, 3 queen beds, 1.5 bathrooms
30 Aug – 4 Sept
4.97 out of 5 average rating, 127 reviews
Home in Briarcliff Manor
Hudson River Views: Briarcliff Manor Home w/ Deck
4 bedrooms, 4 beds, 6 bathrooms
21–26 Jul
Superhost
Room in Ossining
Freshly updated room
1 double bed, WC
11–16 Oct
4.94 out of 5 average rating, 32 reviews
Guest favourite
Townhouse in White Plains
Charming 3BR Home - Quiet Stay, Close to NYC
3 bedrooms, 4 beds, 1 bathroom
3–8 Aug
4.96 out of 5 average rating, 130 reviews
Top guest favourite
Chalet in Philipstown
Cozy A-Frame in the Trees · 20 min to WP· 1 hr NYC
3 bedrooms, 2 bathrooms
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, 1 bathroom
3–8 Aug
4.98 out of 5 average rating, 382 reviews
Top guest favourite
Guest suite in Mount Kisco
Spacious, private retreat 45 mins to NYC
1 bedroom, 3 beds, 1 bathroom
8–13 Aug
4.98 out of 5 average rating, 141 reviews
Top guest favourite
Guest house in Elmsford
Private Guest Suite
2 bedrooms, 2 queen beds, 1 bathroom
5–10 Aug
5.0 out of 5 average rating, 34 reviews