A wooden boardwalk winding through a forest with autumn foliage.

Ossining Hotel Guide - Hotels with Pool in Ossining, New York

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Check availability on Ossining Hotels with Pool

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 €1,049
includes taxes & fees
15 Jul - 16 Jul
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 €1,401
includes taxes & fees
15 Jul - 16 Jul
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, (1,011 reviews)
  • cleanliness
    Majestic seasonal pool beckons with mountain views, perfect for summer relaxation after exploring scenic Bear Mountain trails.
The price is €183
includes taxes & fees
15 Jul - 16 Jul
Overlook Lodge at Bear Mountain
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, (398 reviews)
  • cleanliness
    Seasonal splash paradise with a refreshing outdoor pool and fitness centre creates an invigorating summer escape in Danbury.
The price is €107
includes taxes & fees
2 Aug - 3 Aug
Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG
Seasonal outdoor pool

Ethan Allen Hotel

Ethan Allen Hotel
3.5 star property
Danbury
8.0 out of 10, Very good, (1,312 reviews)
  • cleanliness
    Serene seasonal pool retreat beckons with refreshing dips and resort-like relaxation in a beautiful, quiet setting.
The price is €126
includes taxes & fees
19 Jul - 20 Jul
Ethan Allen Hotel
Indoor pool

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1,133 reviews)
  • cleanliness
    Splash into year-round luxury at this indoor pool retreat just steps from premium shopping outlets.
The price is €141
includes taxes & fees
2 Aug - 3 Aug
Hampton Inn Harriman Woodbury
Land view from property

Heidi's Inn

Heidi's Inn
2.5 star property
Brewster
8.8 out of 10, Excellent, (870 reviews)
  • cleanliness
    Refreshing pool escape surrounds this garden hotel with tranquil loungers and shady cabanas.
The price is €140
includes taxes & fees
21 Jul - 22 Jul
Heidi's Inn
Indoor pool, seasonal outdoor pool

Tarrytown House Estate

Tarrytown House Estate
3.5 star property
Tarrytown
8.2 out of 10, Very good, (1,172 reviews)
  • cleanliness
    Soak up sunshine or swim indoors at this peaceful Hudson River estate with seasonal pool options.
The price is €177
includes taxes & fees
21 Jul - 22 Jul
Tarrytown House Estate
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, (1,013 reviews)
  • cleanliness
    Slip into serenity at this tranquil indoor pool retreat with sun loungers for post-adventure relaxation.
The price is €142
includes taxes & fees
15 Jul - 16 Jul
Sleepy Hollow Hotel, a Dolce by Wyndham
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, (1,017 reviews)
  • cleanliness
    Dive into a seasonal pool oasis in Mount Kisco, where sun loungers invite relaxation just minutes from the airport.
The price is €147
includes taxes & fees
9 Aug - 10 Aug
Hotel MTK Mount Kisco
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

Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

10/10 Excellent
"Christina was extremely helpful when we were checking inn"
Beth 2-night trip
Posted less than an hour ago
Hampton Inn White Plains/Tarrytown

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: Features 2 restaurants, an indoor pool and complimentary wireless Internet access. Hampton Inn White Plains/Tarrytown: Hotel located near Westchester County Center. Offers complimentary wireless Internet access, an indoor pool and a 24-hour fitness centre. Hyatt Regency Greenwich: Features a seasonal outdoor pool, an indoor pool and a sauna. Sonesta White Plains Downtown: Offers 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 Teatown Lake Reservation 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.