Photo by Linda Zanetti

Find Hotels with a Pool in Ossining, NY

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check availability on Ossining Hotels with a Pool

Tonight
7 Aug - 8 Aug
Tomorrow
8 Aug - 9 Aug
This weekend
8 Aug - 10 Aug
Next weekend
15 Aug - 17 Aug

Top Ossining Hotels with a Pool

Summer Castle: Pool, Game Room, BBQ - Pet Friendly
Pool

Summer Castle: Pool, Game Room, BBQ - Pet Friendly

8.6 out of 10, Excellent, (4)
"We booked the property because our family is growing too large for all of the children and grandchildren to spend the holidays together. The “holiday house” as our 4 year old coined it was the perfect place to spend Christmas and Hanukkah. Large yet cozy and very well appointed. All of our communication with proprietors was prompt and helpful, and they had the driveway salted and plowed within hours of the (very picturesque) snowfall the day before Christmas. I would happily book here again. "
The price is AED 2,571
AED 4,548 total
includes taxes & fees
25 Aug - 26 Aug
Summer Castle: Pool, Game Room, BBQ - Pet Friendly
2-bedroom condo in charming Wilton with AC, fitness room, WiFi
Sport court

2-bedroom condo in charming Wilton with AC, fitness room, WiFi

The price is AED 1,568
AED 2,920 total
includes taxes & fees
20 Aug - 21 Aug
2-bedroom condo in charming Wilton with AC, fitness room, WiFi
The Luxury downtown. Pool Jim basketball
Iron/ironing board, WiFi, bed sheets

The Luxury downtown. Pool Jim basketball

The price is AED 882
AED 1,124 total
includes taxes & fees
23 Aug - 24 Aug
The Luxury downtown. Pool Jim basketball
Residence Inn Stamford Downtown
Indoor pool

Residence Inn Stamford Downtown

3.0 star property
9.4 out of 10, Exceptional, (354)
"Excellent customer service! Lovely lobby and rooms"
The price is AED 955
AED 1,098 total
includes taxes & fees
17 Aug - 18 Aug
Residence Inn Stamford Downtown
Courtyard by Marriott Stamford Downtown
Indoor pool

Courtyard by Marriott Stamford Downtown

3.0 star property
9.0 out of 10, Wonderful, (804)
"Overall great stay "
The price is AED 823
AED 946 total
includes taxes & fees
17 Aug - 18 Aug
Courtyard by Marriott Stamford Downtown
Live the luxury lifestyl 2 bedroom Pool Gym, basketball court middle of downtown
2 bedrooms

Live the luxury lifestyl 2 bedroom Pool Gym, basketball court middle of downtown

2.0 star property
The price is AED 1,152
AED 1,490 total
includes taxes & fees
9 Aug - 10 Aug
Live the luxury lifestyl 2 bedroom Pool Gym, basketball court middle of downtown
The Armon Stamford Hotel & Conference
Indoor pool

The Armon Stamford Hotel & Conference

2.5 star property
7.8 out of 10, Good, (505)
"Clean nice hotel, great staff"
The price is AED 503
AED 578 total
includes taxes & fees
11 Aug - 12 Aug
The Armon Stamford Hotel & Conference
La Quinta Inn & Suites by Wyndham Stamford / New York City
Indoor pool, a heated pool

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

3.0 star property
6.6 out of 10, (686)
"The service was wonderful, I enjoyed the breakfast and the convenience of the diner."
The price is AED 328
AED 377 total
includes taxes & fees
28 Aug - 29 Aug
La Quinta Inn & Suites by Wyndham Stamford / New York City
Residence Inn Marriott Danbury
Indoor pool

Residence Inn Marriott Danbury

3.0 star property
8.2 out of 10, Very Good, (320)
"Nice staff. Clean hotel with a good breakfast. Mattress on pull out couch needs upgraded"
The price is AED 532
AED 612 total
includes taxes & fees
24 Aug - 25 Aug
Residence Inn Marriott Danbury
Ethan Allen Hotel
Seasonal outdoor pool

Ethan Allen Hotel

3.5 star property
7.8 out of 10, Good, (1010)
"Great hotel"
The price is AED 316
AED 363 total
includes taxes & fees
24 Aug - 25 Aug
Ethan Allen Hotel
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.

Top Ossining Hotel Reviews

Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

10/10 Excellent
"Excellent hotel with quality accommodations! The bed was super comfortable and the room beautifully decored. We enjoyed our 2night stay."
Sharon 2-night trip
Posted 2 days ago
Crowne Plaza Suffern - Mahwah by IHG

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: Hotel located near Westchester County Center. Features complimentary wireless internet access, an indoor pool, and a 24-hour fitness center. Hampton Inn White Plains/Tarrytown: Offers 2 restaurants, an indoor pool, and 2 bars. Royal Regency Hotel: Features continental, an indoor pool, and free self parking. Crowne Plaza Suffern - Mahwah by IHG: Provides complimentary wired internet access, a seasonal outdoor pool, and free self parking.
What is there to see and do in Ossining?
Explore places like Woodbury Common Premium Outlets while you're in the area. Surround yourself with nature at Depot Square and Ossining Dog Park.
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.