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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
Oct 26 - Oct 27
Tomorrow
Oct 27 - Oct 28
This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

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 modern living room with a sectional sofa, a coffee table, and large windows offering a view of trees.
A large, two-story house with a prominent front entrance, multiple windows, and a driveway.

1. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
Ossining
$950 nightly
$1,059 total
Nov 4 - Nov 5
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 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.
A spacious living room with a large window, a grey sofa with patterned cushions, and a wooden coffee table.

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

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Ossining
$818 nightly
$840 total
Nov 4 - Nov 5
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 lounge with leather sofas, a patterned rug, and red pendant lights.
A modern building with a glass facade, a red door, and a staircase leading to the entrance.
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.
$130 nightly
$148 total
Nov 22 - Nov 23
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 Holiday Inn Express & Suites hotel with a modern design, featuring a covered entrance and American flags.
A hotel room with two beds, a blue sofa, a wooden coffee table, and a painting on the wall.
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.
$138 nightly
$158 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 3 feet 10 inches deep sign, surrounded by a white tiled area, benches, and a glass door leading to another room.
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.
A Sheraton hotel with a modern facade, multiple floors, and a prominent entrance.

5. Sheraton Tarrytown Hotel

Sheraton Tarrytown Hotel
Tarrytown
  • Refreshing indoor pool oasis awaits, complete with a hot tub for post-adventure relaxation.
$135 nightly
$155 total
Nov 22 - Nov 23
Total with taxes and fees
Sheraton Tarrytown Hotel
An indoor swimming pool with a glass ceiling, clear signage indicating depth, and lounge chairs along the sides.
A modern hotel lobby with a kitchen area, seating arrangements, and large windows offering a view of the outdoors.
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.

6. 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.
$135 nightly
$155 total
Nov 15 - Nov 16
Total with taxes and fees
Baymont by Wyndham White Plains - Elmsford
Indoor pool
A hotel room with a large bed, a bedside table with a lamp, a TV, and a bathroom with a mirror and sink.
A modern building with large glass windows, a brick facade, and a curved section.
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.

7. 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.
$127 nightly
$147 total
Nov 22 - Nov 23
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.
A spacious room with a stone fireplace, white sofas, and a large window offering a view of the outdoors.

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.
$143 nightly
$164 total
Nov 1 - Nov 2
Total with taxes and fees
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 historic stone building with a turret, arched entrance, and a covered patio area.
A large building with a white facade and columns, surrounded by a lawn with outdoor seating and string lights.

9. Tarrytown House Estate

Tarrytown House Estate
Tarrytown
  • Soak up sunshine or swim indoors at this peaceful Hudson River estate with seasonal pool options.
$180 nightly
$206 total
Nov 24 - Nov 25
Total with taxes and fees
Tarrytown House Estate
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.
A spacious restaurant with high tables and stools, a bar area, and a television screen displaying a sports game.
An outdoor patio area with tables and chairs, red umbrellas, and flower planters.

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.
$134 nightly
$154 total
Nov 9 - Nov 10
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

Tarrytown House Estate

Tarrytown House Estate

8/10 Good
"Upon arrival the toilet was gross, not sure how housekeeping missed what we saw immediately. Also the shower/tub didn't drain normally. The fridge in the room was turned off when we arrived, when we turned it to medium cool it froze everything in it. Staff however was great and responsive to anything we needed!"
Noreen 2-night trip
Posted 3 hours ago
Tarrytown House Estate
Ethan Allen Hotel

Ethan Allen Hotel

8/10 Good
"Great location, very clean room, and professional front desk staff. Overall, a pleasant and convenient stay!"
Yuxin 1-night trip
Posted 7 hours ago
Ethan Allen Hotel
Hyatt Regency Greenwich

Hyatt Regency Greenwich

8/10 Good
"Parking is overpriced and special parking consideration should be given to guests that are staying at the hotel when big banquet functions are happening."
Wayde 2-night trip
Posted 8 hours ago
Hyatt Regency Greenwich

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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