The Best Hotels with a Pool in Ossining, NY from ￥19,683 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 : Features complimentary wired internet access, a seasonal outdoor pool, and free self parking. Hyatt Regency Greenwich : Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access.

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

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

Ossining

￥230,661 total

includes taxes & fees

Jun 29 - Jun 30

Summer Pool Oasis Custom Bar Arcade Pool Table

Ossining

￥274,625 total

includes taxes & fees

Jun 29 - Jun 30

Overlook Lodge at Bear Mountain

Bear Mountain

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

￥29,010 total

includes taxes & fees

Jun 15 - Jun 16

Ethan Allen Hotel

Danbury

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

￥19,683 total

includes taxes & fees

Jun 21 - Jun 22

Heidi's Inn

Brewster

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

￥25,640 total

includes taxes & fees

Jun 15 - Jun 16

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

Danbury

Seasonal splash paradise with a refreshing outdoor pool and fitness center creates an invigorating summer escape in Danbury.

￥24,140 total

includes taxes & fees

Jul 5 - Jul 6

Tarrytown House Estate

Tarrytown

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

￥29,792 total

includes taxes & fees

Jun 30 - Jul 1

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.

￥28,405 total

includes taxes & fees

Jun 28 - Jun 29

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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

"Beautiful Property and Exceptional Staff"

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

6/10 Okay

"It's very difficult for me to evaluate the hotel at the moment. Now it's undergoing repairs and therefore all the problems are on the face. There were 5 markings on the wall in the room - none of them worked. The girls at the reception are very helpful. Breakfast is simple, you can have a snack."

Tarrytown House Estate

6/10 Okay

"Make no mistake, the grounds are beautiful. The original mansion is also beautiful. However, it is very modern and the addition of recent structural additions to accommodate an increasing number of guests does diminish the property from the magic it claims. Imagine an old mansion property where the atmosphere ends at the door to your room because as soon as you enter the room, you’re now staring at a Hilton or Comfort Inn."

Hampton Inn & Suites Yonkers

8/10 Good

"I’ve booked direct before and don’t remember being charged for parking $15 per day which is crazy since there is ample parking surrounded by businesses who would certainly not use the hotel’s parking. It may be because I booked with Expedia which was a huge savings even with paying for parking, my only surprise."

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: Features complimentary wired internet access, a seasonal outdoor pool, and free self parking. Hyatt Regency Greenwich: Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access.

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 Teatown Lake Reservation 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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Our top choices for Ossining hotels with a pool

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