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Search results; Over 1,000 homes in Ossining

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Guest favourite
Place to stay in Ossining
Top#9
1 bedroom, 1 queen bed, 1 bathroom
18–24 Sept
4.93 out of 5 average rating, 30 reviews
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Top guest favourite
Flat in Ossining
Hudson River Peaceful Getaway, Explore from here
2 bedrooms, 2 beds, 1 bathroom
15–20 Nov
4.96 out of 5 average rating, 555 reviews
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Top guest favourite
Room in Ossining
The hidden gem
1 king bed, 1 bathroom
19–24 Sept
4.99 out of 5 average rating, 76 reviews
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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, 18 reviews
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Home in Croton-on-Hudson
Croton Country House
4 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
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Superhost
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, 51 reviews
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Top guest favourite
Home in Piermont
Piermont Getaway Mt. Village Home. 30 min to NYC
2 bedrooms, 3 queen beds, 1.5 bathrooms
1–6 Sept
4.96 out of 5 average rating, 133 reviews
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Flat in Sleepy Hollow
Large 3BR Sleepy Hollow Apt, Walk to Legend Sites
3 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
New place to stay
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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
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Superhost
Room in Ossining
Freshly updated room
1 double bed, WC
11–16 Nov
4.94 out of 5 average rating, 32 reviews
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Top guest favourite
Home in Valhalla
Valhalla Home
2 bedrooms, 3 beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 31 reviews
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Top guest favourite
Home in Putnam Valley
Luxury Lake House Sauna 1h From NYC
2 bedrooms, 3 beds, 2 bathrooms
5–10 Sept
4.99 out of 5 average rating, 189 reviews
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Top guest favourite
Home in Mount Kisco
Serene Retreat in the Hills w/Jacuzzi
4 bedrooms, 4 beds, 2 bathrooms
2–7 Sept
5.0 out of 5 average rating, 46 reviews
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Home in Chester
Private Estate | Pool, Hot Tub & 10BR Retreat
10 bedrooms, 22 beds, 4.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 5 reviews
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Home in Sleepy Hollow
8BR Hudson Valley Home w/ River Views
8 bedrooms, 10 beds, 4 bathrooms
2–7 Sept
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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, 38 reviews
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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, 170 reviews
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Top guest favourite
Home in Philipstown
Gloves Off Retreat • A Quiet Hudson Valley Escape
3 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 8 reviews