The Best Ossining Hotels with Pools from $127 - Hotels with indoor pools in Ossining, NY

A wooden boardwalk winding through a forest with autumn foliage.

Upfront pricing
Our total price for your stay includes taxes and fees
Treat yourself
Save 10% or more on over 100,000 hotels worldwide with Member Prices
Learn about One Key
Be picky
Search almost a million properties worldwide

Check availability on Ossining Hotels with a Pool

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Ossining hotels with a pool

1. Summer Pool Oasis Custom Bar Arcade Pool Table

Ossining

$1,123 nightly

$1,251 total

Sep 9 - Sep 10

Total with taxes and fees

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

Ossining

$990 nightly

$1,019 total

Sep 8 - Sep 9

Total with taxes and fees

3. 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.

$136 nightly

$156 total

Sep 13 - Sep 14

Total with taxes and fees

4. 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 13 - Sep 14

Total with taxes and fees

5. 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.

$118 nightly

$137 total

Sep 20 - Sep 21

Total with taxes and fees

6. 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.

$151 nightly

$172 total

Sep 20 - Sep 21

Total with taxes and fees

7. Sheraton Tarrytown Hotel

Tarrytown

Refreshing indoor pool oasis awaits, complete with a hot tub for post-adventure relaxation.

$167 nightly

$191 total

Sep 7 - Sep 8

Total with taxes and fees

8. Sleepy Hollow Hotel, a Dolce by Wyndham

Tarrytown

Slip into serenity at this tranquil indoor pool retreat with sun loungers for post-adventure relaxation.

$145 nightly

$166 total

Sep 14 - Sep 15

Total with taxes and fees

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

Hotel Nyack, a JdV by Hyatt Hotel

10/10 Excellent

"Trinity hotel with great food and bar options. The rooms are spacious and the staff is fantastic."

Westchester Marriott

8/10 Good

"Good full service hotel for business"

Armoni Inn & Suites

8/10 Good

"It was okay for a quick stay."

Sleepy Hollow Hotel, a Dolce by Wyndham

8/10 Good

"The front desk staff couldn't have been nicer upon check-in. The hotel lobby and grounds were beautiful, and the restaurant's outdoor patio was quite inviting. My only complaint was that the room doors banged so hard, the guests coming and going in the hallway were a bit disturbing."

Frequently asked questions

What are some hotels with pools in Ossining?

Windrose On Hudson: Hotel, 14-minute walk from Lyndhurst Mansion. 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 center. Royal Regency Hotel: Offers complimentary 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 like Woodbury Common Premium Outlets while you're in the area. Make a point to visit attractions like Teatown Lake Reservation 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

Lodging

Room 1

Upfront pricing

Treat yourself

Be picky

Check availability on Ossining Hotels with a Pool

Our top choices for Ossining hotels with a pool

1. Summer Pool Oasis Custom Bar Arcade Pool Table

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

3. Holiday Inn Express & Suites Hawthorne Elmsford North by IHG