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Search Hotels with Pool in Ossining

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Check availability on Ossining Hotels with Pool

Tonight
22 Dec - 23 Dec
Tomorrow
23 Dec - 24 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

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 ฿12,034
฿28,193 total
includes taxes & fees
5 Jan - 6 Jan 2026
Foliage at Westchester Manor - Near Sleepy Hollow
Indoor pool, open 8:30 AM to 9:30 PM, pool loungers
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet
4.0 star property
Nanuet
9.0 out of 10, Wonderful, (1008)
"Clean room, friendly staff, good breakfast"
United States
Zuriber
The price is ฿3,065
฿3,567 total
includes taxes & fees
4 Jan - 5 Jan 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, (1004)
"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 ฿3,738
฿4,228 total
includes taxes & fees
4 Jan - 5 Jan 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, (1016)
"Great stay and room was very nice"
United States
Emmanuel
The price is ฿3,065
฿3,774 total
includes taxes & fees
11 Jan - 12 Jan 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, (1089)
"One of my favorite hotel to stay in "
United States
Stephen
Ethan Allen Hotel
Outdoor pool
Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG

Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG

Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG
2.5 star property
Danbury
9.2 out of 10, Wonderful, (299)
"Very clean hotel and quiet! Free breakfast was a plus. Would definitely stay here again. Staff was great too"
United States
Scott
The price is ฿3,706
฿4,262 total
includes taxes & fees
28 Dec - 29 Dec
Holiday Inn Express Hotel & Suites Danbury - I-84 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, (1007)
"Room was clean, staff was pleasant, hotel overall was great"
United States
Cara
The price is ฿4,240
฿5,700 total
includes taxes & fees
29 Dec - 30 Dec
Hotel Nyack, a JdV by Hyatt Hotel
Land view from property
Heidi's Inn

Heidi's Inn

Heidi's Inn
2.5 star property
Brewster
8.8 out of 10, Excellent, (809)
"The inn is absolutely charming! Great staff, clean room and the breakfast buffet was great. We will be returning next year! "
United States
SUSAN
The price is ฿3,620
฿3,923 total
includes taxes & fees
28 Dec - 29 Dec
Heidi's Inn
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, (870)
"Great hotel"
United States
Christopher
The price is ฿4,246
฿4,867 total
includes taxes & fees
28 Dec - 29 Dec
Marriott Park Ridge
Indoor pool
Hampton Inn Paramus

Hampton Inn Paramus

Hampton Inn Paramus
2.5 star property
Paramus
9.2 out of 10, Wonderful, (977)
"Rooms were clean, great breakfast and super friendly staff! "
United States
Phaelyn
The price is ฿3,580
฿4,103 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn Paramus
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 room. Cookie time breakfast "
Ivana 4-night trip
Posted 5 days ago
Hampton Inn White Plains/Tarrytown

Frequently asked questions

What are some hotels with pools in Ossining?
Windrose On Hudson: Offers daily, an indoor pool and complimentary high-speed (wired) Internet access. Baymont by Wyndham White Plains - Elmsford: Features complimentary wireless Internet access, an indoor pool and a 24-hour fitness centre. Ramada by Wyndham Bronx: Offers a snack bar/deli, a pool and free self parking. Sonesta White Plains Downtown: Offers free self parking, a seasonal outdoor pool and complimentary wireless Internet access. Royal Regency Hotel: Offers complimentary high-speed (wired) Internet access, an indoor pool and LCD televisions.
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, Thomas J. Watson Research Center and Sing Sing Prison Museum during your stay.
When is the best time to book a hotel with a pool in Ossining?
You may want to consider 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 22°C. Accommodation 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 temperature is 1°C.
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. To venture out into the surrounding area, take a train from Ossining Station. Ossining might not have many public transport options, so consider renting a car to explore more.