A wooden boardwalk winding through a forest with autumn foliage.

Find Hotels with a Pool in Ossining, NY

  • 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 a Pool

Tonight
Sep 11 - Sep 12
Tomorrow
Sep 12 - Sep 13
This weekend
Sep 11 - Sep 13
Next weekend
Sep 18 - Sep 20

Our top choices for Ossining hotels with a pool

House
House
House
House

1. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
Ossining
￥101,734
￥190,410 total
includes taxes & fees
Sep 14 - Sep 15
Summer Pool Oasis Custom Bar Arcade Pool Table
Pool
Living area
Outdoor banquet area
Exterior

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

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Ossining
￥78,739
￥153,881 total
includes taxes & fees
Sep 14 - Sep 15
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Pool
Lobby
Breakfast area
Room

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.
￥19,553
￥22,364 total
includes taxes & fees
Sep 20 - Sep 21
Baymont by Wyndham White Plains - Elmsford
Pool
Room
Breakfast meal
Exterior

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.
￥23,004
￥26,311 total
includes taxes & fees
Oct 4 - Oct 5
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
Pool
Exterior
Lobby
Restaurant

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.
￥19,370
￥26,337 total
includes taxes & fees
Sep 20 - Sep 21
Hotel Nyack, a JdV by Hyatt Hotel
Pool
Point of interest
Lobby
Room

6. 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.
￥18,230
￥21,216 total
includes taxes & fees
Sep 20 - Sep 21
DoubleTree by Hilton Hotel Nanuet
Outdoor pool
Property grounds
Lobby
Restaurant

7. Tarrytown House Estate

Tarrytown House Estate
Tarrytown
  • Soak up sunshine or swim indoors at this peaceful Hudson River estate with seasonal pool options.
￥24,548
￥31,937 total
includes taxes & fees
Sep 13 - Sep 14
Tarrytown House Estate
Pool
Ballroom
Lobby
Lobby

8. 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.
￥22,163
￥25,348 total
includes taxes & fees
Sep 15 - Sep 16
Sleepy Hollow Hotel, a Dolce by Wyndham
Pool
Room
Lobby
Room

9. Hampton Inn Nanuet

Hampton Inn Nanuet
Nanuet
  • Splash into family fun with an indoor pool haven that keeps kids active year-round.
￥16,331
￥19,006 total
includes taxes & fees
Oct 4 - Oct 5
Hampton Inn Nanuet
Pool
Property amenity
Lobby
Exterior

10. Sheraton Tarrytown Hotel

Sheraton Tarrytown Hotel
Tarrytown
  • Refreshing indoor pool oasis awaits, complete with a hot tub for post-adventure relaxation.
￥25,814
￥29,527 total
includes taxes & fees
Sep 17 - Sep 18
Sheraton Tarrytown Hotel
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

Tarrytown House Estate

Tarrytown House Estate

10/10 Excellent
"Awesome stay when you’re visiting NY or just want a nice staycation the staff and amenities always makes us feel like we’re staying at a resort. Can’t wait to stay here for fall activities in the area!"
Kevin 2-night trip
Posted 9 hours ago
Tarrytown House Estate
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

10/10 Excellent
"Beautiful place !"
Christian 2-night trip
Posted 1 day ago
Overlook Lodge at Bear Mountain
Amsterdam Hotel

Amsterdam Hotel

8/10 Good
"Very good value. The gym is a little primitive but functional. Breakfast is basic. The staff was very friendly. Free parking and everything was clean and neat"
david 1-night trip
Posted 1 day ago
Amsterdam Hotel

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: Offers complimentary wired internet access, a seasonal outdoor pool, and free self parking. Royal Regency Hotel: 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 complimentary wireless internet access. Armoni Inn & Suites: Features a sauna, an indoor pool, and spa services.
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 Merchants Square 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