A wooden boardwalk winding through a forest with autumn foliage.

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

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check availability on Ossining Hotels with Pool

Tonight
12 Oct - 13 Oct
Tomorrow
13 Oct - 14 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

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 modern living room with a sectional sofa, a coffee table, and large windows offering a view of trees.
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
€1,011
includes taxes & fees
3 Nov - 4 Nov
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 modern living room with a large window, a sofa with patterned cushions, a wooden coffee table, and a painting on the wall.
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.

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

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Ossining
€895
includes taxes & fees
14 Oct - 15 Oct
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
A swimming pool with lounge chairs and a sunbed area.
Room
A modern building with a glass facade, a red door, and a staircase leading to the entrance.
A modern bar area with a bar counter, multiple stools, and a seating area with a sofa and chairs.

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 Centre.
€138
includes taxes & fees
1 Nov - 2 Nov
Hotel Nyack, a JdV by Hyatt Hotel
An indoor swimming pool with a glass ceiling, clear signage indicating depth, and lounge chairs along the sides.
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.
A hotel corridor with a patterned carpet, a railing, and a reception desk with a glass partition.
A modern hotel lobby with a kitchen area, seating arrangements, and large windows offering a view of the outdoors.

4. 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
includes taxes & fees
2 Nov - 3 Nov
Baymont by Wyndham White Plains - Elmsford
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.
A spacious room with a stone fireplace, white sofas, and a large window offering a view of the outdoors.

5. 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.
€144
includes taxes & fees
18 Oct - 19 Oct
Sleepy Hollow Hotel, a Dolce by Wyndham
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.
€185
includes taxes & fees
8 Nov - 9 Nov
Tarrytown House Estate
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.

7. Sheraton Tarrytown Hotel

Sheraton Tarrytown Hotel
Tarrytown
  • Refreshing indoor pool oasis awaits, complete with a hot tub for post-adventure relaxation.
€146
includes taxes & fees
1 Nov - 2 Nov
Sheraton Tarrytown Hotel
Indoor pool
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 hotel room with a large bed, a bedside table with a lamp, a TV, and a bathroom with a mirror and sink.
A hotel lobby with a reception desk, seating area, and a large window allowing natural light.

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.
€140
includes taxes & fees
27 Oct - 28 Oct
DoubleTree by Hilton Hotel Nanuet
An indoor swimming pool with a tiled floor, a ceiling with a grid pattern, and a view of greenery outside.
A hotel room with two beds, a blue sofa, a wooden coffee table, and a painting on the wall.
A Holiday Inn Express & Suites hotel with a modern design, featuring a covered entrance and American flags.
A modern reception area with a wooden reception desk, a blue accent wall, and a large glass door leading to an outdoor seating area.

9. 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.
€171
includes taxes & fees
12 Nov - 13 Nov
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, green armchairs, 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 lobby with a red sofa set, a fireplace, and a staircase leading to an upper level.

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.
€158
includes taxes & fees
1 Nov - 2 Nov
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

8/10 Good
"Clean comfortable room. Great location."
Anthony 3-night trip
Posted 1 hour ago
Sleepy Hollow Hotel, a Dolce by Wyndham
Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

8/10 Good
"It was very clean. Bed was comfortable. Elevators had issues. The pool water was not as warm as others described. Overall the stay was good. I would stay there again."
Kelly 3-night trip
Posted 2 hours ago
Baymont by Wyndham White Plains - Elmsford
Westchester Marriott

Westchester Marriott

8/10 Good
"We loved the hotel. It was clean and the staff were pleasant. It was only 10-15 minutes from Sleepy Hollow. The only downside was for some reason housekeeping knocked on our door at 8:45am while we were sleeping and woke us up. It was our last day and we wanted to sleep in a bit. Check out wasn’t until noon. As my husband was getting up to answer the door, she opened the door to come in. If the inside latch wasn’t locked then she would have come inside."
Colleen 2-night trip
Posted 5 hours ago
Westchester Marriott
Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

10/10 Excellent
"Front desk staff were amazing. Super helpful and nice."
Donna 2-night trip
Posted 17 hours ago
Hampton Inn White Plains/Tarrytown
Sonesta White Plains Downtown

Sonesta White Plains Downtown

10/10 Excellent
"Clean rooms, friendly staff. Quick check-in and check out process."
Andrew 2-night trip
Posted 2 days ago
Sonesta White Plains Downtown

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 high-speed (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 centre. 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 such as Woodbury Common Premium Outlets while you're in the area. Make a point to visit attractions such as 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 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.