Ossining Hotel with Pool

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Ossining Hotel with Pool

Our top choices for Ossining hotels with a pool

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

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Ossining
9.2 out of 10, Wonderful, (7 reviews)
"Super fun location! Host was very helpful. The house is very comfortable for large groups "
United States
natalie l.
The price is HK$3,716
HK$7,480 total
includes taxes & fees
23 Mar - 24 Mar
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

NEW 45 Wolden Rd Ossining NY 10562

NEW 45 Wolden Rd Ossining NY 10562
2.0 star property
Ossining
The price is HK$3,893
HK$8,293 total
includes taxes & fees
15 Mar - 16 Mar
NEW 45 Wolden Rd Ossining NY 10562

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very good, (1,003 reviews)
"The stone lodges are cute and cozy and the staff were quick and helpful if you needed anything. Great for a short stay at a reasonable price."
United States
Judith
The price is HK$754
HK$854 total
includes taxes & fees
19 Mar - 20 Mar
Overlook Lodge at Bear Mountain

Heidi's Inn

Heidi's Inn
2.5 star property
Brewster
8.8 out of 10, Excellent, (823 reviews)
"Clean room with very friendly and helpfull staff with a light breakfast "
United States
Christopher
The price is HK$1,012
HK$1,097 total
includes taxes & fees
10 Mar - 11 Mar
Heidi's Inn

Ethan Allen Hotel

Ethan Allen Hotel
3.5 star property
Danbury
8.0 out of 10, Very good, (1,168 reviews)
"Clean room | Staff | Breakfast | Business-friendly"
United States
Eimy
The price is HK$720
HK$829 total
includes taxes & fees
15 Mar - 16 Mar
Ethan Allen Hotel

Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG

Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG
2.5 star property
Danbury
9.2 out of 10, Wonderful, (331 reviews)
"We enjoyed our stay. "
United States
Anne
The price is HK$993
HK$1,142 total
includes taxes & fees
29 Mar - 30 Mar
Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG

Charming 1-bedroom apartment in Carmel with WiFi, AC

Charming 1-bedroom apartment in Carmel with WiFi, AC
Carmel Hamlet
9.0 out of 10, Wonderful, (2 reviews)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
The price is HK$1,056
HK$2,179 total
includes taxes & fees
10 Mar - 11 Mar
Charming 1-bedroom apartment in Carmel with WiFi, AC

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1,071 reviews)
"Easy check in, clean room, very good breakfast."
United States
Robert
The price is HK$827
HK$1,019 total
includes taxes & fees
17 Mar - 18 Mar
Hampton Inn Harriman Woodbury

Hotel MTK Mount Kisco

Hotel MTK Mount Kisco
3.0 star property
Mount Kisco
8.6 out of 10, Excellent, (1,005 reviews)
"Great hotel. The town is nice. "
United States
Eric
The price is HK$1,084
HK$1,240 total
includes taxes & fees
29 Mar - 30 Mar
Hotel MTK Mount Kisco

Hampton Inn Paramus

Hampton Inn Paramus
2.5 star property
Paramus
9.2 out of 10, Wonderful, (1,002 reviews)
"Staff was courteous and helpful, room was very clean, bed comfortable, and excellent breakfast!"
United States
George Ann
The price is HK$837
HK$960 total
includes taxes & fees
15 Mar - 16 Mar
Hampton Inn Paramus
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Choose what matters most at hotels with a pool in Ossining

Top Ossining Hotel Reviews

Frequently asked questions

What are some hotels with pools in Ossining?
Windrose On Hudson: Offers daily, an indoor pool and complimentary high-speed (wired) Internet access. Baymont by Wyndham White Plains - Elmsford: Provides a snack bar/deli, a pool and free self parking. DoubleTree by Hilton Hotel Nanuet: Offers complimentary wireless Internet access, an indoor pool and a 24-hour fitness centre. LIV Hotel Bronx - Newly Built: Offers a seasonal outdoor pool, an indoor pool and a sauna. Royal Regency Hotel: Provides complimentary high-speed (wired) Internet access, an indoor pool and LCD televisions.
What is there to see and do in Ossining?
Surround yourself with nature at Teatown Lake Reservation and Merchants Square. Discover sights such as Sing Sing Prison Museum, Sing Sing Correctional Facility and Thomas J. Watson Research Center during your stay.
When is the best time to book a hotel with a pool in Ossining?
You may want to consider 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 22°C. Accommodation 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 temperature is 1°C.
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. To venture out into the surrounding area, take a train from Ossining Station. Ossining might not have many public transport options, so consider renting a car to explore more.

Explore a world of travel with Expedia