The Best Hotels with a Pool in Ossining, NY from ₩182,388 in 2026

Q: What are some hotels with pools in Ossining?

Windrose On Hudson : Offers a seasonal outdoor pool, an indoor pool, and a sauna. Tarrytown House Estate : Hotel located near Westchester County Center. Provides daily, an indoor pool, and complimentary wired internet access. Baymont by Wyndham White Plains - Elmsford : Hotel located near Westchester County Center. Features complimentary wireless internet access, an indoor pool, and a 24-hour fitness center. Sonesta White Plains Downtown : Offers 2 restaurants, an indoor pool, and complimentary wireless internet access. Hyatt Regency Greenwich : Offers a snack bar/deli, a seasonal outdoor pool, and free self parking.

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Our top choices for Ossining hotels with a pool

1. Summer Pool Oasis Custom Bar Arcade Pool Table

Ossining

₩2,152,062 total

includes taxes & fees

Aug 4 - Aug 5

Indoor pool, open 10:00 AM to 8:00 PM, sun loungers

2. Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

Hawthorne

Discover a relaxing escape with a pristine indoor pool sanctuary and poolside loungers for serene relaxation year-round.

₩237,595 total

includes taxes & fees

Aug 30 - Aug 31

Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas

3. Hotel Nyack, a JdV by Hyatt Hotel

Nyack

Seasonal poolside bliss awaits with free cabanas, loungers, and umbrellas at this upscale retreat near Palisades Center.

₩273,376 total

includes taxes & fees

Aug 13 - Aug 14

Indoor pool, open 8:30 AM to 9:30 PM, sun loungers

4. DoubleTree by Hilton Hotel Nanuet

Nanuet

Sink into this pristine hotel's sun-lounger lined indoor pool and hot tub oasis, just moments from Rockland Lake State Park.

₩205,187 total

includes taxes & fees

Aug 13 - Aug 14

5. Baymont by Wyndham White Plains - Elmsford

Elmsford

Splash into relaxation at this well-maintained indoor pool with lifeguard service and extended hours.

₩221,261 total

includes taxes & fees

Aug 23 - Aug 24

6. Tarrytown House Estate

Tarrytown

Soak up sunshine or swim indoors at this peaceful Hudson River estate with seasonal pool options.

₩282,849 total

includes taxes & fees

Aug 2 - Aug 3

Indoor pool, open 9:00 AM to 11:00 AM, sun loungers

7. Sleepy Hollow Hotel, a Dolce by Wyndham

Tarrytown

Slip into serenity at this tranquil indoor pool retreat with sun loungers for post-adventure relaxation.

₩248,004 total

includes taxes & fees

Aug 9 - Aug 10

8. Sheraton Tarrytown Hotel

Tarrytown

Refreshing indoor pool oasis awaits, complete with a hot tub for post-adventure relaxation.

₩236,276 total

includes taxes & fees

Aug 16 - Aug 17

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Choose what matters most at hotels with a pool in Ossining

Breakfast included

Hot tub

Top Ossining Hotel Reviews

Baymont by Wyndham White Plains - Elmsford

10/10 Excellent

"Clean room. Great amenities."

Ethan Allen Hotel

10/10 Excellent

"The Ethan Allen Hotel is where you want to stay in Danbury. The front desk staff are warm and welcoming. The rooms are clean. The beds are comfortable. The pool was still chilly in late July but was very nice. The Patio area adjacent to the pool has a Butane Fire pit that is perfect for sitting around and conversing with family. The Restaurant and bar are quite cozy and welcoming. I would like to give a warm thank-you to Marie at the front desk, Ruben at the restaurant, and Jeff manning the bar; all for their superior service and attentiveness. On a side note; when the main chef had an emergency and the dinner menu was cut very short due to his absence, the rest of the staff filled in and came up with a wonderful alternative menu and saved the day! When I return to Danbury, I WILL stay at the Ethan Allen Hotel again! I highly recommend it!"

Frequently asked questions

What are some hotels with pools in Ossining?

Windrose On Hudson: Offers a seasonal outdoor pool, an indoor pool, and a sauna. Tarrytown House Estate: Hotel located near Westchester County Center. Provides daily, an indoor pool, and complimentary wired internet access. Baymont by Wyndham White Plains - Elmsford: Hotel located near Westchester County Center. Features complimentary wireless internet access, an indoor pool, and a 24-hour fitness center. Sonesta White Plains Downtown: Offers 2 restaurants, an indoor pool, and complimentary wireless internet access. Hyatt Regency Greenwich: Offers a snack bar/deli, a seasonal outdoor pool, and free self parking.

What is there to see and do in Ossining?

Explore places like Woodbury Common Premium Outlets while you're in the area. Make a point to visit attractions like Louis Engel Waterfront Park and Labyrinth.

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.

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Check availability on Ossining Hotels with a Pool

Our top choices for Ossining hotels with a pool

1. Summer Pool Oasis Custom Bar Arcade Pool Table