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Search results; Over 1,000 homes in Ossining

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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, 560 reviews
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Top guest favourite
Room in Ossining
The hidden gem
1 king bed, 1 bathroom
11–16 Oct
4.99 out of 5 average rating, 81 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
14–19 Nov
5.0 out of 5 average rating, 20 reviews
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Top guest favourite
Guest suite in Briarcliff Manor
Enjoy Summer Living "Stone Haven" Hudson Valley
1 bedroom, 2 beds, 1 bathroom
1–6 Nov
5.0 out of 5 average rating, 54 reviews
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Home in Briarcliff Manor
Hudson River Views: Briarcliff Manor Home w/ Deck
4 bedrooms, 4 beds, 6 bathrooms
28 Nov – 3 Dec
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Featured hotel
Hotel in West Point
The Thayer Hotel at West Point, Selected by hotel
1 bedroom, 1 double bed, 1 bathroom
22–27 Oct
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Flat in Croton-on-Hudson
Luxury 2bd⭐Comfort+Style⭐
2 bedrooms, 2 queen beds, 1 bathroom
3–8 Nov
4.98 out of 5 average rating, 386 reviews
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Home in Croton-on-Hudson
Croton Country House
4 bedrooms, 4 beds, 2 bathrooms
26–31 Oct
5.0 out of 5 average rating, 3 reviews
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Superhost
Room in Ossining
Freshly updated room
1 double bed, WC
8–13 Dec
4.94 out of 5 average rating, 32 reviews
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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
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Top guest favourite
Home in Mount Kisco
Incredible barn in country setting
2 bedrooms, 2 beds, 1 bathroom
1–6 Oct
4.94 out of 5 average rating, 161 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
1–6 Nov
4.99 out of 5 average rating, 191 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
17–22 Oct
5.0 out of 5 average rating, 8 reviews
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Top guest favourite
Guest suite in Sleepy Hollow
Sleepy Hollow Private Apartment Airbnb
1 queen bed, 1 bathroom
14–21 Nov
4.97 out of 5 average rating, 69 reviews
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Guest favourite
Home in Suffern
Group Retreat | Pool, Hot Tub & Gourmet Kitchen
4 bedrooms, 13 beds, 3 bathrooms
1–6 Oct
4.91 out of 5 average rating, 55 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
2–7 Nov
4.93 out of 5 average rating, 175 reviews
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Top guest favourite
Home in Yorktown Heights
Cozy getaway 1 hr from NYC!
3 bedrooms, 4 beds, 3 bathrooms
4–9 Oct
4.91 out of 5 average rating, 186 reviews
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Room in Yonkers
Private Suite w/ Private Entry + Bath
1 bed, 1 bathroom
11–16 Oct
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Top guest favourite
Flat in Croton-on-Hudson
Croton Nook - Cozy Getaway
2 beds, 1 bathroom
18–23 Oct
5.0 out of 5 average rating, 38 reviews