The Best Hotels with a Pool in Ossining, NY from NT$4,217 in 2026

Q: What are some hotels with pools in Ossining?

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

Boardwalk over marshland on the trail at Teatown Lake Reservation in Ossining, New York.

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Our top choices for Ossining hotels with a pool

Summer Pool Oasis Custom Bar Arcade Pool Table

Ossining

NT$50,810 total

includes taxes & fees

Jun 23 - Jun 24

Overlook Lodge at Bear Mountain

Bear Mountain

Majestic seasonal pool beckons with mountain views, perfect for summer relaxation after exploring scenic Bear Mountain trails.

NT$6,572 total

includes taxes & fees

Jun 21 - Jun 22

Ethan Allen Hotel

Danbury

Serene seasonal pool retreat beckons with refreshing dips and resort-like relaxation in a beautiful, quiet setting.

NT$4,217 total

includes taxes & fees

Jun 28 - Jun 29

Heidi's Inn

Brewster

Refreshing pool escape surrounds this garden hotel with tranquil loungers and shady cabanas.

NT$5,054 total

includes taxes & fees

Jun 21 - Jun 22

Seasonal outdoor pool, open 11:00 AM to 8:00 PM, sun loungers

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.

NT$5,599 total

includes taxes & fees

Jun 28 - Jun 29

Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG

Peekskill

Luxurious indoor pool sanctuary offers year-round aquatic relaxation while overlooking Hudson Valley's scenic landscapes.

NT$5,491 total

includes taxes & fees

Jul 5 - Jul 6

Seasonal outdoor pool, open 9 AM to 7:00 PM, sun loungers

Residence Inn By Marriott New Rochelle

Downtown Rochelle

Refreshing plunge into serenity at this seasonal outdoor pool with loungers for sun-soaked afternoons.

NT$6,033 total

includes taxes & fees

Jul 2 - Jul 3

Tarrytown House Estate

Tarrytown

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

NT$5,873 total

includes taxes & fees

Jun 30 - Jul 1

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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

"Atrium is beautiful. Room was clean and modern."

Hotel Nyack, a JdV by Hyatt Hotel

10/10 Excellent

"This is a hidden Gem that puts you so close to all there is to do i. Nyack, beautiful decorum, beautiful ire, I would highly recommend getting the balcony view, the staff is courteous and helpful, it is a hop kip and a jump from the Mall. The restaurant is amazing, a beautiful place to hold events. This will definitely be my go to weekend getaway."

La Quinta Inn & Suites by Wyndham Stamford / New York City

10/10 Excellent

"Inexpensive clean, not the most glamorous place, but for the price it was appropriate. I would go back again and I would recommend for someone who is looking for something within their budget. Staff was friendly as well thank you."

Sonesta White Plains Downtown

8/10 Good

"Third time staying here at the renovated hotel. Room was clean and comfortable. Nice beds and pillows, and thermostat/AC, shower, etc all worked well. Self parking was complementary, which is good. Staff always friendly and helpful. No complaints about the room, lobby or staff. Cons: The $30 daily "resort fee" add-on is ridiculous -- as it is with most hotels. Silly and excessive. Don't make me spend $60 for two people at breakfast so I can get a "credit" -- especially when paying $270/night. A regular coffee in lobby was $6.50. Not latte or fancy drink, just a coffee. Crazy. (Go across street to Whole Foods and it's about $2.50). Also, and this was particularly disappointing: ice machines on multiple floors were broken. So we had to search for ice on several floors. Not sure if this is being remedied or simply hotel not caring about it. Just a few nagging cons for an otherwise solid hotel in the area."

Frequently asked questions

What are some hotels with pools in Ossining?

Windrose On Hudson: Hotel located near Westchester County Center. Offers daily, an indoor pool, and complimentary wired internet access. Baymont by Wyndham White Plains - Elmsford: Provides a seasonal outdoor pool, an indoor pool, and a sauna. Tarrytown House Estate: Offers 2 restaurants, an indoor pool, and complimentary wireless internet access. Royal Hotel Bronx: Offers complimentary wired internet access, a seasonal outdoor pool, and free self parking. 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?

Make a point to visit attractions like Merchants Square and Labyrinth. Discover sights such as Sing Sing Correctional Facility, Travelers Rest, and Pleasant Square 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.

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Our top choices for Ossining hotels with a pool