A wooden boardwalk winding through a forest with autumn foliage.

Find Hotels with a Pool in Ossining, NY

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Check availability on Ossining Hotels with a Pool

Tonight
Sep 13 - Sep 14
Tomorrow
Sep 14 - Sep 15
Next weekend
Sep 18 - Sep 20
In two weeks
Sep 25 - Sep 27

Our top choices for Ossining hotels with a pool

1. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
Ossining
$1,107 nightly
$1,233 total
Sep 14 - Sep 15
Total with taxes and fees
Summer Pool Oasis Custom Bar Arcade Pool Table

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!

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

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.
$148 nightly
$169 total
Sep 20 - Sep 21
Total with taxes and fees
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

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

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

7. Tarrytown House Estate

Tarrytown House Estate
Tarrytown
  • Soak up sunshine or swim indoors at this peaceful Hudson River estate with seasonal pool options.
$178 nightly
$203 total
Sep 22 - Sep 23
Total with taxes and fees
Tarrytown House Estate

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.
$145 nightly
$166 total
Sep 27 - Sep 28
Total with taxes and fees
Sleepy Hollow Hotel, a Dolce by Wyndham

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

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 20 - Sep 21
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

Tarrytown House Estate

Tarrytown House Estate

8/10 Good
"Lovely property, clean and comfortable. The building and landscaping are a little behind schedule. Not so much as to avoid a stay."
Scott 1-night trip
Posted less than an hour ago
Tarrytown House Estate
Amsterdam Hotel

Amsterdam Hotel

10/10 Excellent
"Best value in lodging anywhere."
Allan 4-night trip
Posted 3 hours ago
Amsterdam Hotel
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 1 day ago
Overlook Lodge at Bear Mountain
Sonesta White Plains Downtown

Sonesta White Plains Downtown

10/10 Excellent
"Nnnnxxxxxxxxxxxx. Xxxxxxxxxx"
Garry 3-night trip
Posted 1 day ago
Sonesta White Plains Downtown

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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