Photo by louann ohora

Ossining Hotel Guide - Hotels with Pool in Ossining, New York

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Ossining Hotels with Pool

Tonight
29 Nov - 30 Nov
Tomorrow
30 Nov - 1 Dec
Next weekend
5 Dec - 7 Dec
In two weeks
12 Dec - 14 Dec

Top Ossining Hotels with Pool

Pool
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Ossining
9.0 out of 10, Wonderful, (6)
"We booked the property because our family is growing too large for all of the children and grandchildren to spend the holidays together. The “holiday house” as our 4 year old coined it was the perfect place to spend Christmas and Hanukkah. Large yet cozy and very well appointed. All of our communication with proprietors was prompt and helpful, and they had the driveway salted and plowed within hours of the (very picturesque) snowfall the day before Christmas. I would happily book here again. "
United States
Matthew W.
The price is €1,221
includes taxes & fees
1 Dec - 2 Dec
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
House
Foliage at Westchester Manor - Near Sleepy Hollow

Foliage at Westchester Manor - Near Sleepy Hollow

2.0 star property
Ossining
The price is €852
includes taxes & fees
10 Dec - 11 Dec
Foliage at Westchester Manor - Near Sleepy Hollow
Seasonal outdoor pool
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 star property
Bear Mountain
8.4 out of 10, Very good, (1023)
"Parking was very easy, beautiful area, very nice staff"
United States
Elizabeth
The price is €116
includes taxes & fees
30 Nov - 1 Dec
Overlook Lodge at Bear Mountain
Terrace/patio
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, (1013)
"Awesome place"
United States
Nichole
The price is €115
includes taxes & fees
14 Dec - 15 Dec
Hotel Nyack, a JdV by Hyatt Hotel
Indoor pool, open 8:30 AM to 9:30 PM, pool loungers
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

4.0 star property
Nanuet
8.8 out of 10, Excellent, (1011)
"Very clean very beautiful very good hospitality would stay again"
United States
Bobby
The price is €106
includes taxes & fees
14 Dec - 15 Dec
DoubleTree by Hilton Hotel Nanuet
Indoor pool
Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1016)
"Staff were friendly and very helpful and the hotel was well cared after. "
United States
Jason
The price is €101
includes taxes & fees
11 Dec - 12 Dec
Hampton Inn Harriman Woodbury
Seasonal outdoor pool, open 8:00 AM to 9:00 PM, free pool cabanas
Heidi's Inn

Heidi's Inn

2.5 star property
Brewster
8.8 out of 10, Excellent, (806)
"Very nice clean motel! "
United States
James
The price is €103
includes taxes & fees
30 Nov - 1 Dec
Heidi's Inn
Meeting facility
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, (1011)
"Everything was just perfect from the staff to the hotel facilities "
United States
Kristal
The price is €125
includes taxes & fees
30 Nov - 1 Dec
Hotel NoMa, Trademark Collection by Wyndham
Outdoor pool
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, (285)
"breakfast good and quiet room "
United States
Robert
The price is €110
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG
Seasonal outdoor pool
Ethan Allen Hotel

Ethan Allen Hotel

3.5 star property
Danbury
7.8 out of 10, Good, (1068)
"Great Hotel!"
United States
Steven
Ethan Allen Hotel
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.
View all properties

Top Ossining Hotel Reviews

Sonesta White Plains Downtown

Sonesta White Plains Downtown

10/10 Excellent
"I’ve rarely encountered a hotel in the U.S. with such outstanding hospitality from the staff. The rooms were newly renovated, very clean, and overall it was an excellent hotel."
Kawata 1-night trip
Posted 3 days ago
Sonesta White Plains Downtown

Explore a world of travel with Expedia

Frequently asked questions

What are some hotels with pools in Ossining?
Windrose On Hudson: Offers complimentary wireless Internet access, an indoor pool and a 24-hour fitness centre. Sonesta White Plains Downtown: Offers a seasonal outdoor pool, an indoor pool and a sauna. Royal Regency Hotel: Provides a snack bar/deli, a pool and free self parking. Ramada by Wyndham Bronx: Features complimentary high-speed (wired) Internet access, an indoor pool and LCD televisions. Tarrytown House Estate: Features a sauna, an indoor pool and free self parking.
What is there to see and do in Ossining?
Surround yourself with nature at Teatown Lake Reservation and Kitchawan Preserve. 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.