Find Hotels with a Pool in Ossining, NY

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Ossining Hotels with a Pool

Tonight
Mar 2 - Mar 3
Tomorrow
Mar 3 - Mar 4
This weekend
Mar 6 - Mar 8
Next weekend
Mar 13 - Mar 15

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)
"Super fun location! Host was very helpful. The house is very comfortable for large groups "
United States
natalie l.
$943 nightly
The price is $971
Mar 16 - Mar 17
Total with taxes and fees
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Villa | 5 bedrooms

NEW 45 Wolden Rd Ossining NY 10562

NEW 45 Wolden Rd Ossining NY 10562
2.0 star property
Ossining
$980 nightly
The price is $1,091
Mar 15 - Mar 16
Total with taxes and fees
NEW 45 Wolden Rd Ossining NY 10562
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, (1,003 reviews)
"The stone lodges are cute and cozy and the staff were quick and helpful if you needed anything. Great for a short stay at a reasonable price."
United States
Judith
$101 nightly
The price is $115
Mar 9 - Mar 10
Total with taxes and fees
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, (822 reviews)
"Clean room with very friendly and helpfull staff with a light breakfast "
United States
Christopher
$129 nightly
The price is $140
Mar 3 - Mar 4
Total with taxes and fees
Heidi's Inn
Seasonal outdoor pool

Ethan Allen Hotel

Ethan Allen Hotel
3.5 star property
Danbury
7.8 out of 10, Good, (1,154 reviews)
"Clean room | Staff | Breakfast | Business-friendly"
United States
Eimy
$97 nightly
The price is $112
Mar 10 - Mar 11
Total with taxes and fees
Ethan Allen Hotel
Private kitchen

Charming 1-bedroom apartment in Carmel with WiFi, AC

Charming 1-bedroom apartment in Carmel with WiFi, AC
Carmel Hamlet
9.0 out of 10, Wonderful, (2 reviews)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
$257 nightly
The price is $279
Mar 3 - Mar 4
Total with taxes and fees
Charming 1-bedroom apartment in Carmel with WiFi, AC
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, (330 reviews)
"We enjoyed our stay. "
United States
Anne
$127 nightly
The price is $146
Mar 29 - Mar 30
Total with taxes and fees
Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG
Seasonal outdoor pool, open 11:00 AM to 8:00 PM, sun loungers

Hotel MTK Mount Kisco

Hotel MTK Mount Kisco
3.0 star property
Mount Kisco
8.6 out of 10, Excellent, (1,003 reviews)
"Great hotel. The town is nice. "
United States
Eric
$139 nightly
The price is $159
Mar 15 - Mar 16
Total with taxes and fees
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, (1,066 reviews)
"Easy check in, clean room, very good breakfast."
United States
Robert
$106 nightly
The price is $130
Mar 12 - Mar 13
Total with taxes and fees
Hampton Inn Harriman Woodbury
Indoor pool

Hampton Inn Paramus

Hampton Inn Paramus
2.5 star property
Paramus
9.2 out of 10, Wonderful, (1,000 reviews)
"Staff was courteous and helpful, room was very clean, bed comfortable, and excellent breakfast!"
United States
George Ann
$107 nightly
The price is $123
Mar 15 - Mar 16
Total with taxes and fees
Hampton Inn Paramus
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
Hot tub

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now

Top Ossining Hotel Reviews

Amsterdam Hotel

Amsterdam Hotel

10/10 Excellent
"Cleanliness, friendly staff"
Bernadette 1-night trip
Posted 3 days ago
Amsterdam Hotel

Frequently asked questions

What are some hotels with pools in Ossining?
Windrose On Hudson: Offers daily, an indoor pool, and complimentary wired internet access. Baymont by Wyndham White Plains - Elmsford: Provides a snack bar/deli, a pool, and free self parking. DoubleTree by Hilton Hotel Nanuet: Offers complimentary wireless internet access, an indoor pool, and a 24-hour fitness center. LIV Hotel Bronx - Newly Built: Offers a seasonal outdoor pool, an indoor pool, and a sauna. Royal Regency Hotel: Provides complimentary wired internet access, an indoor pool, and LCD televisions.
What is there to see and do in Ossining?
Surround yourself with nature at Teatown Lake Reservation and Kitchawan Preserve. Discover sights such as Sing Sing Prison Museum, Sing Sing Correctional Facility, and Thomas J. Watson Research Center 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.

Explore a world of travel with Expedia