Search Ossining hotels

  • 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 prices for these dates

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Ossining hotels

Windrose On Hudson

Windrose On Hudson
3.0 star property
Ossining
8.2 out of 10, Very good, (112 reviews)
"Great staff"
United States
Timothy
The price is NZ$342
includes taxes & fees
2 Mar - 3 Mar
Windrose On Hudson

NEW 45 Wolden Rd Ossining NY 10562

NEW 45 Wolden Rd Ossining NY 10562
2.0 star property
Ossining
The price is NZ$1,504
includes taxes & fees
17 Mar - 18 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, (1,004 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 NZ$192
includes taxes & fees
1 Mar - 2 Mar
Overlook Lodge at Bear Mountain

Ardsley Acres Hotel Westchester

Ardsley Acres Hotel Westchester
2.0 star property
Ardsley
8.6 out of 10, Excellent, (1,006 reviews)
"The rooms are renovated and modern, very comfortable beds. "
United States
Ravel
Ardsley Acres Hotel Westchester

La Quinta Inn & Suites by Wyndham Stamford / New York City

La Quinta Inn & Suites by Wyndham Stamford / New York City
3.0 star property
Waterside
6.8 out of 10, (1,135 reviews)
"Average Stay.. Was ok.. Lots of restaurants nearby.. Close to highway Staff was ok "
United States
Jaime
The price is NZ$176
includes taxes & fees
22 Feb - 23 Feb
La Quinta Inn & Suites by Wyndham Stamford / New York City

Courtyard by Marriott Mahwah

Courtyard by Marriott Mahwah
3.0 star property
Mahwah
8.2 out of 10, Very good, (1,006 reviews)
"Needs a fresh look and feel "
United States
Linda
The price is NZ$203
includes taxes & fees
25 Feb - 26 Feb
Courtyard by Marriott Mahwah

Inn on the Hudson

Inn on the Hudson
2.0 star property
Peekskill
7.0 out of 10, Good, (1,006 reviews)
"The staff was really welcoming!"
United States
Devis
The price is NZ$169
includes taxes & fees
22 Feb - 23 Feb
Inn on the Hudson

Red Carpet Inn

Red Carpet Inn
2.0 star property
Cove - East Side - Shippan
6.6 out of 10, (1,006 reviews)
"It was decent for a nights rest an hour away from the city. Not bad "
United States
Roxxanna
The price is NZ$145
includes taxes & fees
1 Mar - 2 Mar
Red Carpet Inn

Super 8 by Wyndham Mahwah

Super 8 by Wyndham Mahwah
2.5 star property
Mahwah
7.4 out of 10, Good, (1,001 reviews)
"Room was very spacious and the staff was extremely helpful!!!!"
United States
Lydia
The price is NZ$147
includes taxes & fees
22 Feb - 23 Feb
Super 8 by Wyndham Mahwah

DoubleTree by Hilton Mahwah

DoubleTree by Hilton Mahwah
4.0 star property
Mahwah
7.8 out of 10, Good, (947 reviews)
"Great rate, restful sleep, and courteous staff. "
United States
Martin
The price is NZ$216
includes taxes & fees
23 Feb - 24 Feb
DoubleTree by Hilton Mahwah

Marriott Park Ridge

Marriott Park Ridge
3.5 star property
Park Ridge
8.8 out of 10, Excellent, (904 reviews)
"Staff is always so pleasant ❤️"
United States
Roange Angie
The price is NZ$273
includes taxes & fees
22 Feb - 23 Feb
Marriott Park Ridge

HYATT house White Plains

HYATT house White Plains
3.0 star property
West Harrison
8.6 out of 10, Excellent, (1,005 reviews)
"This is an amazing hotel with friendly staff."
United States
Cesar A.
The price is NZ$326
includes taxes & fees
28 Feb - 1 Mar
HYATT house White Plains

Amsterdam Hotel

Amsterdam Hotel
2.0 star property
Downtown Stamford
8.4 out of 10, Very good, (1,741 reviews)
"Great Hotel"
United States
Debra
Amsterdam Hotel

Heidi's Inn

Heidi's Inn
2.5 star property
Brewster
8.8 out of 10, Excellent, (822 reviews)
"Clean room with very friendly and helpfull staff with a light breakfast "
United States
Christopher
The price is NZ$232
includes taxes & fees
23 Feb - 24 Feb
Heidi's Inn

Royal Regency Hotel

Royal Regency Hotel
3.5 star property
Northwest Yonkers
8.4 out of 10, Very good, (2,488 reviews)
"The rooms clean , breakfast great staff nice "
United States
Rodolfo
The price is NZ$197
includes taxes & fees
26 Feb - 27 Feb
Royal Regency Hotel

Hampton Inn & Suites Mahwah

Hampton Inn & Suites Mahwah
2.5 star property
Mahwah
8.8 out of 10, Excellent, (1,462 reviews)
"Great place to stay. "
United States
Omar
The price is NZ$183
includes taxes & fees
28 Feb - 1 Mar
Hampton Inn & Suites Mahwah

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
2.5 star property
Hawthorne
9.0 out of 10, Wonderful, (992 reviews)
"great stay"
United States
Janet
The price is NZ$256
includes taxes & fees
22 Feb - 23 Feb
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1,059 reviews)
"Easy check in, clean room, very good breakfast."
United States
Robert
The price is NZ$216
includes taxes & fees
23 Feb - 24 Feb
Hampton Inn Harriman Woodbury

Garner Hotel Mahwah by IHG

Garner Hotel Mahwah by IHG
2.5 star property
Mahwah
9.0 out of 10, Wonderful, (422 reviews)
"Clean room ,and very friendly staff."
United States
Aira
The price is NZ$217
includes taxes & fees
24 Feb - 25 Feb
Garner Hotel Mahwah by IHG

Comfort Inn Brewster

Comfort Inn Brewster
2.5 star property
Brewster
9.0 out of 10, Wonderful, (544 reviews)
"Always great service and clean, comfy rooms. Breakfast is also decent every time, which isn’t always the case at hotels "
United States
Jared
The price is NZ$227
includes taxes & fees
26 Feb - 27 Feb
Comfort Inn Brewster
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.

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Ossining attractions

Learn more about Ossining

Sing Sing Prison Museum offers a fascinating glimpse into America's most notorious correctional facility, with guided tours by former officers. Hike the scenic Old Croton Aqueduct Trail and then grab lunch at one of the diverse restaurants along the Hudson River waterfront.

Main building at Maryknoll
Photo by louann ohora
Open Photo by louann ohora

Top Ossining Hotel Reviews

More cheap accommodation in Ossining

Frequently asked questions

Where is the best place to stay in Ossining?
Windrose On Hudson is one of the top choices for your stay based on our traveller data. This hotel offers free parking and a fitness centre. Other good options for your visit to the area are Baymont by Wyndham White Plains - Elmsford and Sonesta White Plains Downtown. See all available top hotels, or vacation rentals in Ossining.
What are some of the best holiday rentals that Ossining has to offer?
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!: This highly rated holiday home rental in Ossining is located near skiing, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games. See all vacation rentals in Ossining.
If I need to cancel my hotel reservation in Ossining, will I receive a refund?
Yes, most hotel bookings are fully refundable if you cancel prior to the accommodation's cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If your reservation is non-refundable, you may still be able to cancel and receive a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Ossining.
What are some accommodation options with pools in Ossining?
Baymont by Wyndham White Plains - Elmsford: Hotel located near Westchester County Center. Offers daily, an indoor pool and complimentary high-speed (wired) Internet access. Sonesta White Plains Downtown and DoubleTree by Hilton Hotel Nanuet are a couple of other choices with an on-site pool. View all hotels with pools in Ossining.
What's it like to stay in Ossining?
Visitors can enjoy all that Ossining has to offer, including the restaurants, parks and golf courses. Tourists can also enjoy the city's university setting, monuments and museums. In Ossining, there are 33 hotels and other accommodation options to choose from. Find out more about Ossining.
What should I do while I'm visiting Ossining?
Cultural venues include Sing Sing Prison Museum and Ossining Historical Society. Landmarks like Sing Sing Correctional Facility, Thomas J. Watson Research Center and Ossining Public Library might be worth a visit. Natural beauty is on display at Merchants Square, Teatown Lake Reservation and Pleasant Square. Take a look at what more there is to see and do in Expedia's Ossining guide.
What's the best way to get around Ossining?
To venture out into the surrounding area, take a train from Ossining Station. If you want to venture out around the area, you may want a rental car in Ossining for your journey.
What's the weather like in Ossining?
The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of 1°C. Average annual precipitation for Ossining is 1302 mm.

Explore a world of travel with Expedia