The Best Hotels with a Pool in Ossining, NY from ￥23,122 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 : Provides complimentary wired internet access, a seasonal outdoor pool, and free self parking. Armoni Inn & Suites : Hotel located near Westchester County Center. Features complimentary wireless internet access, an indoor pool, and a 24-hour fitness center. LIV Hotel Bronx - Newly Built : Features 2 restaurants, an indoor pool, and complimentary wireless internet access. Royal Regency Hotel : Hotel, 1-minute walk from Bear Mountain State Park. Offers a full-service spa, a seasonal outdoor pool, and a snack bar/deli.

A wooden boardwalk winding through a forest with autumn foliage.

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Our top choices for Ossining hotels with a pool

A backyard with a swimming pool, lounge chairs, a brick wall, and a wooden deck.

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

Ossining

￥132,743 total

includes taxes & fees

Nov 4 - Nov 5

A swimming pool with lounge chairs and a wooden deck, surrounded by trees and a building with a sloped roof.

2. Summer Pool Oasis Custom Bar Arcade Pool Table

Ossining

￥155,671 total

includes taxes & fees

Nov 4 - Nov 5

An indoor swimming pool with a tiled floor, a ceiling with a grid pattern, and a view of greenery outside.

3. 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.

￥24,859 total

includes taxes & fees

Nov 15 - Nov 16

A swimming pool with lounge chairs and a sunbed area.

4. 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.

￥23,178 total

includes taxes & fees

Nov 18 - Nov 19

An indoor swimming pool with a glass ceiling, clear signage indicating depth, and lounge chairs along the sides.

5. Baymont by Wyndham White Plains - Elmsford

Elmsford

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

￥24,858 total

includes taxes & fees

Nov 16 - Nov 17

An indoor swimming pool with a wooden ceiling and brick walls.

6. Sleepy Hollow Hotel, a Dolce by Wyndham

Tarrytown

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

￥25,676 total

includes taxes & fees

Nov 2 - Nov 3

An indoor swimming pool with a 3 feet 10 inches deep sign, surrounded by a white tiled area, benches, and a glass door leading to another room.

7. Sheraton Tarrytown Hotel

Tarrytown

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

￥24,354 total

includes taxes & fees

Nov 22 - Nov 23

A swimming pool with a clear blue water, surrounded by lounge chairs and umbrellas, and a building with a modern design in the background.

8. Hotel MTK Mount Kisco

Mount Kisco

Dive into a seasonal pool oasis in Mount Kisco, where sun loungers invite relaxation just minutes from the airport.

￥24,129 total

includes taxes & fees

Nov 9 - Nov 10

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Choose what matters most at hotels with a pool in Ossining

Breakfast included

Hot tub

Top Ossining Hotel Reviews

Hyatt Regency Greenwich

10/10 Excellent

"I will definitely be back. such a great hotel. Especially love the lobby and staff; the rooms are super cute and cozy."

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: Provides complimentary wired internet access, a seasonal outdoor pool, and free self parking. Armoni Inn & Suites: Hotel located near Westchester County Center. Features complimentary wireless internet access, an indoor pool, and a 24-hour fitness center. LIV Hotel Bronx - Newly Built: Features 2 restaurants, an indoor pool, and complimentary wireless internet access. Royal Regency Hotel: Hotel, 1-minute walk from Bear Mountain State Park. Offers a full-service spa, a seasonal outdoor pool, and a snack bar/deli.

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

2. Summer Pool Oasis Custom Bar Arcade Pool Table