A wooden boardwalk winding through a forest with autumn foliage.

Hotels with Swimming Pools in Ossining

  • 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 Swimming Pools

Tonight
24 Aug - 25 Aug
Tomorrow
25 Aug - 26 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

Our top choices for Ossining hotels with a pool

5 bedrooms
5 bedrooms
5 bedrooms
5 bedrooms

1. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
Ossining
S$1,555
includes taxes & fees
1 Sept - 2 Sept
Summer Pool Oasis Custom Bar Arcade Pool Table
Indoor pool, open 10:00 AM to 8:00 PM, pool loungers
Exterior
Exterior
In-room safe, soundproofing, iron/ironing board, free WiFi

2. 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.
S$187
includes taxes & fees
13 Sept - 14 Sept
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
Indoor pool
Lobby
Free daily self-service breakfast
Desk, laptop workspace, blackout curtains, iron/ironing board

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.
S$189
includes taxes & fees
30 Aug - 31 Aug
Baymont by Wyndham White Plains - Elmsford
Indoor pool, open 8:30 AM to 9:30 PM, pool loungers
Bar (on property)
Lobby
Premium bedding, in-room safe, desk, laptop workspace

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.
S$182
includes taxes & fees
7 Sept - 8 Sept
DoubleTree by Hilton Hotel Nanuet
Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas
Lobby
Exterior
Premium bedding, pillow-top beds, in-room safe, desk

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 Centre.
S$217
includes taxes & fees
31 Aug - 1 Sept
Hotel Nyack, a JdV by Hyatt Hotel
Indoor pool, seasonal outdoor pool
Lobby
Property grounds
Dinner and brunch served

6. Tarrytown House Estate

Tarrytown House Estate
Tarrytown
  • Soak up sunshine or swim indoors at this peaceful Hudson River estate with seasonal pool options.
S$263
includes taxes & fees
25 Aug - 26 Aug
Tarrytown House Estate
Indoor pool, open 9:00 AM to 11:00 AM, pool loungers
Lobby
Ballroom
Exterior

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.
S$218
includes taxes & fees
26 Aug - 27 Aug
Sleepy Hollow Hotel, a Dolce by Wyndham
Indoor pool
Exterior
Lobby
Fitness facility

8. Sheraton Tarrytown Hotel

Sheraton Tarrytown Hotel
Tarrytown
  • Refreshing indoor pool oasis awaits, complete with a hot tub for post-adventure relaxation.
S$208
includes taxes & fees
30 Aug - 31 Aug
Sheraton Tarrytown Hotel
Indoor pool
Premium bedding, pillow-top beds, in-room safe, desk
Premium bedding, pillow-top beds, in-room safe, desk
Lobby

9. Hampton Inn Nanuet

Hampton Inn Nanuet
Nanuet
  • Splash into family fun with an indoor pool haven that keeps kids active year-round.
S$156
includes taxes & fees
31 Aug - 1 Sept
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

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: Hotel located near Westchester County Center. Features complimentary wireless Internet access, an indoor pool and a 24-hour fitness centre. Royal Regency Hotel: Offers complimentary high-speed (wired) Internet access, a seasonal outdoor pool and free self parking. Sonesta White Plains Downtown: Features 2 restaurants, an indoor pool and complimentary wireless Internet access. Armoni Inn & Suites: Offers a snack bar/deli, a seasonal outdoor pool and free self parking.
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 Teatown Lake Reservation 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.

Explore a world of travel with Expedia