A wooden boardwalk winding through a forest with autumn foliage.

Find Hotels with a Pool in Ossining, NY

Check availability on Ossining Hotels with a Pool

Tonight
Oct 20 - Oct 21
Tomorrow
Oct 21 - Oct 22
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

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 traditional Tudor-style house with a spacious front yard, a stone wall, and a well-maintained garden.
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
$977 nightly
$1,089 total
Nov 3 - Nov 4
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.
An outdoor dining area with tables set for a formal event, featuring candles, glassware, and floral centerpieces.
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
$868 nightly
$892 total
Nov 3 - Nov 4
Total with taxes and fees
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
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.
Room

3. 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.
$127 nightly
$145 total
Nov 18 - Nov 19
Total with taxes and fees
Hotel Nyack, a JdV by Hyatt Hotel
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 modern breakfast bar with a variety of food options, including cereal and hot food. There are signs indicating breakfast and hot food availability.
A hotel room with two beds, a blue sofa, a wooden coffee table, and a painting on the wall.

4. 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.
$129 nightly
$148 total
Nov 15 - Nov 16
Total with taxes and fees
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
An indoor swimming pool with a glass ceiling, clear signage indicating depth, and lounge chairs along the sides.
A modern hotel lobby with a seating area, a kitchen, and a bar.
A modern hotel lobby with a kitchen area, seating arrangements, and large windows offering a view of the outdoors.
A hotel corridor with a patterned carpet, a railing, and a reception desk with a glass partition.

5. 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.
$138 nightly
$157 total
Nov 1 - Nov 2
Total with taxes and fees
Baymont by Wyndham White Plains - Elmsford
An indoor swimming pool with a 3 feet 10 inches deep sign, surrounded by a white tiled area, benches, and a glass door leading to another room.
A spacious lobby with a reception desk, sofas, and a coffee table. There are multiple seating areas and a large window providing natural light.
A modern office space with two monitors, a white desk, black chairs, and a large abstract painting on the wall.
A gym with exercise equipment, large windows, and a wooden reception desk.

6. Sheraton Tarrytown Hotel

Sheraton Tarrytown Hotel
Tarrytown
  • Refreshing indoor pool oasis awaits, complete with a hot tub for post-adventure relaxation.
$143 nightly
$164 total
Nov 1 - Nov 2
Total with taxes and fees
Sheraton Tarrytown 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 building with a white facade and columns, surrounded by a lawn with outdoor seating and string lights.
A large, historic building with a red roof, surrounded by a well-maintained garden with statues and flower beds.

7. 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
Nov 8 - Nov 9
Total with taxes and fees
Tarrytown House Estate
Indoor pool
A hotel lobby with a reception desk, seating area, and a large window allowing natural light.
A spacious lobby with a modern design, featuring a seating area with sofas and armchairs, a decorative wall panel, and a large window providing natural light.
A modern building with large glass windows, a brick facade, and a curved section.

8. 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.
$135 nightly
$157 total
Nov 1 - Nov 2
Total with taxes and fees
DoubleTree by Hilton Hotel Nanuet
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 corridor with stone walls, large windows, and a central chandelier.
An outdoor patio with tables and chairs, surrounded by large umbrellas.

9. 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.
$143 nightly
$164 total
Nov 1 - Nov 2
Total with taxes and fees
Sleepy Hollow Hotel, a Dolce by Wyndham
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.
An outdoor patio area with tables and chairs, red umbrellas, and flower planters.
A spacious restaurant with high tables and stools, a bar area, and a television screen displaying a sports game.

10. 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
Nov 16 - Nov 17
Total with taxes and fees
Hotel MTK Mount Kisco
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

Sleepy Hollow Hotel, a Dolce by Wyndham

Sleepy Hollow Hotel, a Dolce by Wyndham

10/10 Excellent
"Beautiful hotel. Loved the balcony with"
Steven 1-night trip
Posted less than an hour ago
Sleepy Hollow Hotel, a Dolce by Wyndham
Tarrytown House Estate

Tarrytown House Estate

10/10 Excellent
"Beautiful property, great breakfast and restaurant on site, and friendly and helpful staff."
Michael 2-night trip
Posted 3 hours ago
Tarrytown House Estate
Hyatt Regency Greenwich

Hyatt Regency Greenwich

10/10 Excellent
"Property has everything you could want including a movie theater! Beautiful hotel!"
Linda 2-night trip
Posted 11 hours ago
Hyatt Regency Greenwich
J House Greenwich

J House Greenwich

10/10 Excellent
"Very quaint, clean hotel with nice coffee shop and restaurant"
Mary 2-night trip
Posted 18 hours ago
J House Greenwich
The Stamford Hotel

The Stamford Hotel

10/10 Excellent
"Very clean, very good service!"
Eliana 1-night trip
Posted 20 hours ago
The Stamford Hotel
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

10/10 Excellent
"It was a very scenic area and the hotel was really clean and comfortable. Lots a things to do in the area."
Danielle 1-night trip
Posted 2 days ago
Overlook Lodge at Bear Mountain
Westchester Marriott

Westchester Marriott

8/10 Good
"C"
Prashant 1-night trip
Posted 2 days ago
Westchester Marriott

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. Features complimentary wireless internet access, an indoor pool, and a 24-hour fitness center. LIV Hotel Bronx - Newly Built: Features 2 restaurants, an indoor pool, and complimentary wireless internet access. Royal Regency Hotel: 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 Louis Engel Waterfront Park 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.

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