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Find Hotels with a Pool in Ossining, NY

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Check availability on Ossining Hotels with a Pool

Tonight
Sep 12 - Sep 13
Tomorrow
Sep 13 - Sep 14
Next weekend
Sep 18 - Sep 20
In two weeks
Sep 25 - Sep 27

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 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.
A traditional Tudor-style house with a spacious front yard, a stone wall, and a well-maintained garden.
A modern living room with a sectional sofa, a coffee table, and large windows offering a view of trees.

1. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
Ossining
$1,096 nightly
$1,221 total
Sep 15 - Sep 16
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.
An outdoor dining area with tables set for a formal event, featuring candles, glassware, and floral centerpieces.

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

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Ossining
$969 nightly
$997 total
Sep 14 - Sep 15
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 seating area, a kitchen, and a bar.
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.

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.
$127 nightly
$145 total
Sep 20 - Sep 21
Total with taxes and fees
Baymont by Wyndham White Plains - Elmsford
An indoor swimming pool with a tiled floor, a ceiling with a grid pattern, and a view of greenery outside.
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.
A modern breakfast bar with a variety of food options, including cereal and hot food. There are signs indicating breakfast and hot food availability.

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.
$149 nightly
$170 total
Oct 4 - Oct 5
Total with taxes and fees
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
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.
$149 nightly
$171 total
Sep 20 - Sep 21
Total with taxes and fees
Hotel Nyack, a JdV by Hyatt Hotel
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 spacious lobby with a central seating area, a decorative wall, and a reception desk in the background.
A hotel dining area with multiple tables and chairs, a bar with a counter and bar stools, and two televisions mounted on the wall.

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.
$122 nightly
$142 total
Sep 27 - Sep 28
Total with taxes and fees
DoubleTree by Hilton Hotel Nanuet
A swimming pool with lounge chairs and umbrellas, surrounded by a fence, with a castle-like building in the background.
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.
A spacious lobby with a staircase, seating area, and large windows offering a view of the outdoors.

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
Sep 13 - Sep 14
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.
A spacious interior with a high ceiling, stone walls, and modern furniture.

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.
$137 nightly
$157 total
Sep 30 - Oct 1
Total with taxes and fees
Sleepy Hollow Hotel, a Dolce by Wyndham
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 modern hotel lobby with a long communal table, seating area, and a kitchenette.
A hotel room with a bed, a desk, a chair, a TV, and a painting on the wall.

9. 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
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 Sheraton hotel with a modern facade, multiple floors, and a prominent entrance.
A modern office space with two monitors, a white desk, black chairs, and a large abstract painting on the wall.

10. Sheraton Tarrytown Hotel

Sheraton Tarrytown Hotel
Tarrytown
  • Refreshing indoor pool oasis awaits, complete with a hot tub for post-adventure relaxation.
$167 nightly
$191 total
Sep 17 - Sep 18
Total with taxes and fees
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

Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

10/10 Excellent
"Comfortable stay! Would stay again!"
David 3-night trip
Posted 2 hours ago
Hampton Inn White Plains/Tarrytown
Hotel Nyack, a JdV by Hyatt Hotel

Hotel Nyack, a JdV by Hyatt Hotel

8/10 Good
"Clean room. Staff were friendly. Available parking spaces. Excellent stay only minor thing was that the AC vent was directly over the bed so the cold air blows right toward the bed. Other than that the stay was great."
Jasmine 1-night trip
Posted 3 hours ago
Hotel Nyack, a JdV by Hyatt Hotel
Hyatt Regency Greenwich

Hyatt Regency Greenwich

10/10 Excellent
"I used to go to this hotel, the breakfast buffet was excellent, but it’s not available anymore"
Ricardo 3-night trip
Posted 3 hours ago
Hyatt Regency Greenwich
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

8/10 Good
"This location and its history made this Inn a great stopover night for us as we travelled down the East Coast. The scenery is beautiful and the staff are helpful and friendly. This would would be a great place to meet with family members and/or friends to enjoy sharing a cottage (with 6 rooms and a common area) to enjoy a few nights or week together. There is a lot to do in the area and the porch of the cottage lends itself to just sitting and admiring the natural surroundings, especially the lake!"
Nancy 1-night trip
Posted 3 hours ago
Overlook Lodge at Bear Mountain
Sonesta White Plains Downtown

Sonesta White Plains Downtown

10/10 Excellent
"Nnnnxxxxxxxxxxxx. Xxxxxxxxxx"
Garry 3-night trip
Posted 6 hours ago
Sonesta White Plains Downtown
Tarrytown House Estate

Tarrytown House Estate

10/10 Excellent
"The setting is absolutely beautiful. My room was spacious and lovely, although slightly worn at the edges, but it didn’t matter because the bed was super comfortable, and the linens were lovely and the bathtub was deep and relaxing. It has everything you need. There is a refrigerator in the room a big screen TV a safe, blackout curtains and I can’t wait to go back!"
Stephanie 2-night trip
Posted 20 hours ago
Tarrytown House Estate
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 2 days 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.

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