A wooden boardwalk winding through a forest with autumn foliage.

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Check availability on Ossining Hotels with Pool

This weekend
6 Nov - 8 Nov
Next weekend
13 Nov - 15 Nov

Our top choices for Ossining hotels with a pool

A spacious indoor area with large windows, modern furniture, and a view of a landscaped outdoor area.

1. Windrose On Hudson

Windrose On Hudson
3.0 star property
Ossining
8.6 out of 10, Excellent, (283 reviews)
"Would 100% stay again"
United States
Michael
The price is ฿5,101
฿5,681 total
includes taxes & fees
22 Nov - 23 Nov
Windrose On Hudson
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

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is ฿17,594
฿35,597 total
includes taxes & fees
9 Nov - 10 Nov
Summer Pool Oasis Custom Bar Arcade Pool Table
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.
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Choose what matters most at hotels with a pool in Ossining

Breakfast included
Hot tub

Top Ossining Hotel Reviews

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

10/10 Excellent
"Loooove it"
Kendall 1-night trip
Posted 2 days ago
Overlook Lodge at Bear Mountain
Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

10/10 Excellent
"The room was pretty clean and comfortable, staff was friendly"
Zack 2-night trip
Posted 3 days ago
Hampton Inn White Plains/Tarrytown

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 high-speed (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 centre. 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 such as Woodbury Common Premium Outlets while you're in the area. Make a point to visit attractions such as 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 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.