A wooden boardwalk winding through a forest with autumn foliage.

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
Sep 27 - Sep 28
Tomorrow
Sep 28 - Sep 29
Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11

Our top choices for Ossining hotels with a pool

A swimming pool with lounge chairs and a wooden deck, surrounded by trees and a building with a sloped roof.
A large, two-story house with a prominent front entrance, multiple windows, and a driveway.
A modern living room with a sectional sofa, a coffee table, and large windows offering a view of trees.
A spacious living room with a large window, a ceiling fan, a dining area with a table and chairs, and a staircase leading to an upper level.

1. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
Ossining
$1,107 nightly
$1,233 total
Sep 28 - Sep 29
Total with taxes and fees
Summer Pool Oasis Custom Bar Arcade Pool Table
A backyard with a swimming pool, lounge chairs, a brick wall, and a wooden deck.
A spacious living room with a large window, a grey sofa with patterned cushions, and a wooden coffee table.
A Tudor-style house with a brick facade, a steeply pitched roof, and a large front yard with a paved patio and a stone wall.
A modern living room with a large window, a sofa with patterned cushions, a wooden coffee table, and a painting on the wall.

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

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Ossining
$915 nightly
$937 total
Sep 30 - Oct 1
Total with taxes and fees
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
An indoor swimming pool with a glass ceiling, clear signage indicating depth, and lounge chairs along the sides.
A modern hotel lobby with a kitchen area, seating arrangements, and large windows offering a view of the outdoors.
A modern hotel lobby with a seating area, a kitchen, and a bar.
A hotel room with a large bed, a desk, and a chair. There is a window with curtains and a wall with a geometric patterned design.

3. Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford
Elmsford
  • Splash into relaxation at this well-maintained indoor pool with lifeguard service and extended hours.
$144 nightly
$164 total
Oct 4 - Oct 5
Total with taxes and fees
Baymont by Wyndham White Plains - Elmsford
An indoor swimming pool with clear glass ceilings, stone walls, and multiple lounge chairs around the pool area.
A modern building with large glass windows, a brick facade, and a curved section.
A hotel dining area with multiple tables and chairs, a bar with a counter and bar stools, and two televisions mounted on the wall.
A spacious lobby with a central seating area, a decorative wall, and a reception desk in the background.

4. DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet
Nanuet
  • Sink into this pristine hotel's sun-lounger lined indoor pool and hot tub oasis, just moments from Rockland Lake State Park.
$130 nightly
$152 total
Oct 27 - Oct 28
Total with taxes and fees
DoubleTree by Hilton Hotel Nanuet
A swimming pool with lounge chairs and a sunbed area.
A modern building with a glass facade, a red door, and a staircase leading to the entrance.
A modern lounge with leather sofas, a patterned rug, and red pendant lights.

5. Hotel Nyack, a JdV by Hyatt Hotel

Hotel Nyack, a JdV by Hyatt Hotel
Nyack
  • Seasonal poolside bliss awaits with free cabanas, loungers, and umbrellas at this upscale retreat near Palisades Center.
$162 nightly
$185 total
Oct 26 - Oct 27
Total with taxes and fees
Hotel Nyack, a JdV by Hyatt Hotel
A swimming pool with lounge chairs and umbrellas, surrounded by a fence, with a castle-like building in the background.
A spacious lobby with a staircase, seating area, and large windows offering a view of the outdoors.
A large, historic building with a red roof, surrounded by a well-maintained garden with statues and flower beds.
A large building with a white facade and columns, surrounded by a lawn with outdoor seating and string lights.

6. Tarrytown House Estate

Tarrytown House Estate
Tarrytown
  • Soak up sunshine or swim indoors at this peaceful Hudson River estate with seasonal pool options.
$181 nightly
$207 total
Oct 4 - Oct 5
Total with taxes and fees
Tarrytown House Estate
An indoor swimming pool with a wooden ceiling and brick walls.
A modern building with a stone facade and wooden beams, surrounded by a well-maintained lawn and trees.
A spacious room with a stone fireplace, white sofas, and a large window offering a view of the outdoors.
An outdoor patio with tables and chairs, surrounded by large umbrellas.

7. Sleepy Hollow Hotel, a Dolce by Wyndham

Sleepy Hollow Hotel, a Dolce by Wyndham
Tarrytown
  • Slip into serenity at this tranquil indoor pool retreat with sun loungers for post-adventure relaxation.
$137 nightly
$157 total
Oct 18 - Oct 19
Total with taxes and fees
Sleepy Hollow Hotel, a Dolce by Wyndham
An indoor swimming pool with a tiled floor, a ceiling with a grid pattern, and a view of greenery outside.
A modern reception area with a wooden reception desk, a blue accent wall, and a large glass door leading to an outdoor seating area.
A hotel room with two beds, a blue sofa, a wooden coffee table, and a painting on the wall.
A modern breakfast bar with a variety of food options, including cereal and hot food. There are signs indicating breakfast and hot food availability.

8. Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
Hawthorne
  • Discover a relaxing escape with a pristine indoor pool sanctuary and poolside loungers for serene relaxation year-round.
$170 nightly
$194 total
Oct 18 - Oct 19
Total with taxes and fees
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
A swimming pool with a clear blue water, surrounded by lounge chairs and umbrellas, and a building with a modern design in the background.
A spacious lobby with a red sofa set, a fireplace, and a staircase leading to an upper level.
A spacious lobby with a red sofa, green armchairs, a fireplace, and a staircase leading to an upper level.
A spacious restaurant with high tables and stools, a bar area, and a television screen displaying a sports game.

9. Hotel MTK Mount Kisco

Hotel MTK Mount Kisco
Mount Kisco
  • Dive into a seasonal pool oasis in Mount Kisco, where sun loungers invite relaxation just minutes from the airport.
$147 nightly
$168 total
Oct 11 - Oct 12
Total with taxes and fees
Hotel MTK Mount Kisco
An indoor swimming pool with clear water, large windows, and a lifeguard station.
A hotel reception area with a wooden floor, a reception desk, and a large window with a view of the parking lot.
A hotel room with a wooden desk, a green chair, a gray sofa, a kitchenette, and a door with a sign.
A hotel room with a bed, a desk, a chair, a TV, and a painting on the wall.

10. Hampton Inn Nanuet

Hampton Inn Nanuet
Nanuet
  • Splash into family fun with an indoor pool haven that keeps kids active year-round.
$106 nightly
$123 total
Oct 4 - Oct 5
Total with taxes and fees
Hampton Inn Nanuet
View all properties

Choose what matters most at hotels with a pool in Ossining

Breakfast included
Hot tub
4 stars
5 stars
Spa

Top Ossining Hotel Reviews

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

8/10 Good
"The room was a little warm. There was no way to make it cooler."
Marilyn 1-night trip
Posted 4 hours ago
Overlook Lodge at Bear Mountain
Amsterdam Hotel

Amsterdam Hotel

10/10 Excellent
"I am a repeat guest at Amsterdam Hotel starting over five years ago. This is a family-owned and family-run hotel. They are always superb. I live in Hawaii, where we take our "Aloha" seriously. The staff certainly have that "Aloha Spirit we cherish and practice. Thank you, as always -now and in the future. The breakfast provided is appreciated. :)"
Jeffrey 3-night trip
Posted 7 hours ago
Amsterdam Hotel
La Quinta Inn & Suites by Wyndham Stamford / New York City

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

10/10 Excellent
"This was my first time at this hotel. I had heard good things about it from others. There was what I'd call a glitch in my checking-in. The gentleman at the front desk handled this professionally and all went well. The room was very clean and just what I needed for my stay. The breakfast provided was much more than I expected. The location is ideal, though I should mention that parts of the street do not have adequate sidewalks or crossing signals for pedestrians. There is a large Shop-Rite grocery and other shops nearby. I will be back."
Jeffrey 2-night trip
Posted 7 hours ago
La Quinta Inn & Suites by Wyndham Stamford / New York City
Hotel Nyack, a JdV by Hyatt Hotel

Hotel Nyack, a JdV by Hyatt Hotel

10/10 Excellent
"Very nice customer service great restaurant connected to them"
Carlos 1-night trip
Posted 7 hours ago
Hotel Nyack, a JdV by Hyatt Hotel
Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

10/10 Excellent
"Excellent service, clean hotel and good food! Recommended"
Maria 1-night trip
Posted 10 hours ago
Hampton Inn White Plains/Tarrytown
Hampton Inn & Suites Yonkers - Westchester

Hampton Inn & Suites Yonkers - Westchester

8/10 Good
"Nice place, staff was helpful, good breakfast."
Claudine 1-night trip
Posted 2 days ago
Hampton Inn & Suites Yonkers - Westchester

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 wired internet access, a seasonal outdoor pool, and free self parking. Armoni Inn & Suites: Hotel located near Westchester County Center. Offers complimentary wireless internet access, an indoor pool, and a 24-hour fitness center. Royal Regency Hotel: Features 2 restaurants, an indoor pool, and complimentary wireless internet access. LIV Hotel Bronx - Newly Built: 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 like Woodbury Common Premium Outlets while you're in the area. Make a point to visit attractions like Teatown Lake Reservation and Labyrinth.
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