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Find Hotels with a Pool in Ossining, NY

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Check availability on Ossining Hotels with a Pool

Our top choices for Ossining hotels with a pool

House | 5 bedrooms
Foliage at Westchester Manor - Near Sleepy Hollow

Foliage at Westchester Manor - Near Sleepy Hollow

Foliage at Westchester Manor - Near Sleepy Hollow
2.0 star property
Ossining
The price is ₩606,091
₩1,368,154 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Foliage at Westchester Manor - Near Sleepy Hollow
Indoor pool, open 8:30 AM to 9:30 PM, sun loungers
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet
4.0 star property
Nanuet
8.8 out of 10, Excellent, (1008)
"Great staff, clean and the pool was awesome! "
Canada
Aleah
The price is ₩143,301
₩166,766 total
includes taxes & fees
Jan 4 - Jan 5, 2026
DoubleTree by Hilton Hotel Nanuet
Seasonal outdoor pool
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very Good, (1001)
"Staff was incredibly kind and the room was super cozy. The inn is beautiful and there is enough to do around. "
United States
Ryan
The price is ₩174,757
₩197,696 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Overlook Lodge at Bear Mountain
Indoor pool
Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1014)
"Great stay and room was very nice"
United States
Emmanuel
The price is ₩139,806
₩172,138 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Hampton Inn Harriman Woodbury
Seasonal outdoor pool
Ethan Allen Hotel

Ethan Allen Hotel

Ethan Allen Hotel
3.5 star property
Danbury
7.8 out of 10, Good, (1086)
"Great Hotel!"
United States
Steven
Ethan Allen Hotel
Indoor pool
Holiday Inn Express West Point by IHG

Holiday Inn Express West Point by IHG

Holiday Inn Express West Point by IHG
2.5 star property
Fort Montgomery
9.2 out of 10, Wonderful, (212)
"Wonderful stay…excellent staff!"
United States
John
The price is ₩158,603
₩179,421 total
includes taxes & fees
Dec 22 - Dec 23
Holiday Inn Express West Point by IHG
Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas
Hotel Nyack, a JdV by Hyatt Hotel

Hotel Nyack, a JdV by Hyatt Hotel

Hotel Nyack, a JdV by Hyatt Hotel
4.0 star property
Nyack
8.6 out of 10, Excellent, (1008)
"Room was clean, staff was pleasant, hotel overall was great"
United States
Cara
The price is ₩186,506
₩253,098 total
includes taxes & fees
Dec 23 - Dec 24
Hotel Nyack, a JdV by Hyatt Hotel
Property grounds
Hotel NoMa, Trademark Collection by Wyndham

Hotel NoMa, Trademark Collection by Wyndham

Hotel NoMa, Trademark Collection by Wyndham
3.0 star property
New Rochelle
8.2 out of 10, Very Good, (1009)
"Food was good."
United States
Charles
The price is ₩145,386
₩190,177 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hotel NoMa, Trademark Collection by Wyndham
Indoor pool
Hampton Inn Paramus

Hampton Inn Paramus

Hampton Inn Paramus
2.5 star property
Paramus
9.2 out of 10, Wonderful, (973)
"Rooms were clean, great breakfast and super friendly staff! "
United States
Phaelyn
The price is ₩167,385
₩191,864 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hampton Inn Paramus
Indoor pool, seasonal outdoor pool
Marriott Park Ridge

Marriott Park Ridge

Marriott Park Ridge
3.5 star property
Park Ridge
8.8 out of 10, Excellent, (864)
"Great hotel"
United States
Christopher
The price is ₩186,800
₩214,119 total
includes taxes & fees
Dec 21 - Dec 22
Marriott Park Ridge
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Ossining Hotel Reviews

Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

10/10 Excellent
"Clean and comfortable room. Had a room on a non smoking floor which was good. Several people out front entrance smoking different stuff so had to walk through a cloud upon entering.. Needed something to avoid snowy travel and it fit the bill!"
Beatrice 1-night trip
Posted 2 days ago
Hampton Inn White Plains/Tarrytown

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Frequently asked questions

What are some hotels with pools in Ossining?
Windrose On Hudson: Offers daily, an indoor pool, and complimentary wired internet access. Baymont by Wyndham White Plains - Elmsford: Provides complimentary wireless internet access, an indoor pool, and a 24-hour fitness center. Sonesta White Plains Downtown: Offers a snack bar/deli, a pool, and free self parking. Royal Regency Hotel: Features free self parking, a seasonal outdoor pool, and complimentary wireless internet access. DoubleTree by Hilton Hotel Nanuet: Offers a seasonal outdoor pool, an indoor pool, and a sauna.
What is there to see and do in Ossining?
Surround yourself with nature at Teatown Lake Reservation and Merchants Square. Discover sights such as Sing Sing Correctional Facility, Sing Sing Prison Museum, and Ossining Historical Society during your stay.
When is the best time to book a hotel with a pool in Ossining?
You may want to consider an accommodation with an outdoor swimming pool if you're planning to visit Ossining in the warmest months of July, August, or June when the average temp is 71°F. Lodging with an indoor pool may be what you want if you are visiting during the coldest months of January, February, or December when the average temp is 34°F.
What's the best way to travel around Ossining?
Knowing the transportation options in Ossining can help you enjoy the area beyond your hotel pool. If you want to explore the larger area, hop on a train at Ossining Station. Ossining may not have many public transit options to choose from so consider renting a car to explore more.