A wooden boardwalk winding through a forest with autumn foliage.

Hotels with Pool & Resorts in Ossining from NZ$201

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Ossining Hotels with Pool

This weekend
3 Jul - 5 Jul
Next weekend
10 Jul - 12 Jul

Our top choices for Ossining hotels with a pool

Pool

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

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Ossining
9.2 out of 10, Wonderful, (7 reviews)
The price is NZ$2,324
includes taxes & fees
7 July - 8 July
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
House

Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is NZ$2,932
includes taxes & fees
13 July - 14 July
Summer Pool Oasis Custom Bar Arcade Pool Table
Seasonal outdoor pool

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very good, (1,002 reviews)
  • cleanliness
    Majestic seasonal pool beckons with mountain views, perfect for summer relaxation after exploring scenic Bear Mountain trails.
The price is NZ$289
includes taxes & fees
5 July - 6 July
Overlook Lodge at Bear Mountain
Land view from property

Heidi's Inn

Heidi's Inn
2.5 star property
Brewster
8.8 out of 10, Excellent, (864 reviews)
  • cleanliness
    Refreshing pool escape surrounds this garden hotel with tranquil loungers and shady cabanas.
The price is NZ$282
includes taxes & fees
7 July - 8 July
Heidi's Inn
Outdoor pool

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

Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG
2.5 star property
Danbury
9.2 out of 10, Wonderful, (390 reviews)
  • cleanliness
    Seasonal splash paradise with a refreshing outdoor pool and fitness centre creates an invigorating summer escape in Danbury.
The price is NZ$253
includes taxes & fees
26 July - 27 July
Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG
Indoor pool, seasonal outdoor pool

Tarrytown House Estate

Tarrytown House Estate
3.5 star property
Tarrytown
8.2 out of 10, Very good, (1,135 reviews)
  • cleanliness
    Soak up sunshine or swim indoors at this peaceful Hudson River estate with seasonal pool options.
The price is NZ$313
includes taxes & fees
2 Aug - 3 Aug
Tarrytown House Estate
Seasonal outdoor pool

Ethan Allen Hotel

Ethan Allen Hotel
3.5 star property
Danbury
8.0 out of 10, Very good, (1,277 reviews)
  • cleanliness
    Serene seasonal pool retreat beckons with refreshing dips and resort-like relaxation in a beautiful, quiet setting.
The price is NZ$201
includes taxes & fees
5 July - 6 July
Ethan Allen Hotel
Seasonal outdoor pool, open 11:00 AM to 8:00 PM, pool loungers

Hotel MTK Mount Kisco

Hotel MTK Mount Kisco
3.0 star property
Mount Kisco
8.6 out of 10, Excellent, (1,001 reviews)
  • cleanliness
    Dive into a seasonal pool oasis in Mount Kisco, where sun loungers invite relaxation just minutes from the airport.
The price is NZ$296
includes taxes & fees
2 Aug - 3 Aug
Hotel MTK Mount Kisco
Indoor pool

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1,119 reviews)
  • cleanliness
    Splash into year-round luxury at this indoor pool retreat just steps from premium shopping outlets.
The price is NZ$283
includes taxes & fees
26 July - 27 July
Hampton Inn Harriman Woodbury
Indoor pool, open 9:00 AM to 11:00 AM, pool loungers

Sleepy Hollow Hotel, a Dolce by Wyndham

Sleepy Hollow Hotel, a Dolce by Wyndham
3.5 star property
Tarrytown
7.0 out of 10, Good, (1,001 reviews)
  • cleanliness
    Slip into serenity at this tranquil indoor pool retreat with sun loungers for post-adventure relaxation.
The price is NZ$303
includes taxes & fees
7 July - 8 July
Sleepy Hollow Hotel, a Dolce by Wyndham
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.
View all properties

Choose what matters most at hotels with a pool in Ossining

Breakfast included
Spa pool

Top Ossining Hotel Reviews

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

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

8/10 Good
"You get what you pay for - if you're just looking for a clean place to stay, they've got it covered for a good value (although they are currently undergoing a lot of renovations, so the common areas are a bit messier than the rooms). Not particularly convenient to anything, but parking is pretty cheap compared to other areas of Stamford. The team was very cheerful and helpful throughout check-in and our stay."
Christina 2-night trip
Posted 1 hour ago
La Quinta Inn & Suites by Wyndham Stamford / New York City

Frequently asked questions

What are some hotels with pools in Ossining?
Windrose On Hudson: Offers 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. Hampton Inn White Plains/Tarrytown: Offers a seasonal outdoor pool, an indoor pool and a sauna. Sonesta White Plains Downtown: Features 2 restaurants, an indoor pool and complimentary wireless Internet access. Tarrytown House Estate: Provides a snack bar/deli, a seasonal outdoor pool and free self parking.
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 Depot Square 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.