Photo by Linda Zanetti

Ossining Hotels from S$128

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Property class

Top 10 trending Ossining hotels

Windrose On Hudson

2.0 star property
5.0 out of 10, (2)
"I regret I didn’t take pictures, but the scenery was beautiful"
The price is S$325
includes taxes & fees
3 Jul - 4 Jul
Windrose On Hudson

Days Inn by Wyndham Ridgefield

2.0 star property
5.8 out of 10, (849)
"Loved it, the property was great "
The price is S$135
includes taxes & fees
13 Jul - 14 Jul
Days Inn by Wyndham Ridgefield

Amsterdam Hotel

2.0 star property
8.4 out of 10, Very good, (1602)
"The front desk was courteous, firm beds, close amenities. "
Amsterdam Hotel

The Stamford Hotel

3.5 star property
7.8 out of 10, Good, (1060)
"It was a nice hotel."
The price is S$189
includes taxes & fees
10 Jul - 11 Jul
The Stamford Hotel

Stamford Marriott Hotel & Spa

3.5 star property
8.0 out of 10, Very good, (1002)
"Great place to stay."
The price is S$347
includes taxes & fees
13 Jul - 14 Jul
Stamford Marriott Hotel & Spa

Residence Inn Stamford Downtown

3.0 star property
9.4 out of 10, Exceptional, (343)
"Amazing stay"
The price is S$380
includes taxes & fees
11 Jul - 12 Jul
Residence Inn Stamford Downtown

Courtyard by Marriott Stamford Downtown

3.0 star property
9.0 out of 10, Wonderful, (796)
"Nice spot near a lot of cool places."
The price is S$327
includes taxes & fees
11 Jul - 12 Jul
Courtyard by Marriott Stamford Downtown

The Lloyd Stamford, Tapestry Collection by Hilton

3.5 star property
8.8 out of 10, Excellent, (362)
"The hotel was beautiful. The rooms were comfy and loved the shower."
The price is S$265
includes taxes & fees
13 Jul - 14 Jul
The Lloyd Stamford, Tapestry Collection by Hilton

Hampton Inn & Suites Stamford

2.5 star property
8.6 out of 10, Excellent, (1002)
"Great location "
The price is S$301
includes taxes & fees
6 Jul - 7 Jul
Hampton Inn & Suites Stamford

Hilton Stamford Hotel & Executive Meeting Center

3.5 star property
7.4 out of 10, Good, (1003)
"Friendly staff, adequate rooms, but a little shabby"
The price is S$262
includes taxes & fees
6 Jul - 7 Jul
Hilton Stamford Hotel & Executive Meeting Center

The Armon Stamford Hotel & Conference

2.5 star property
7.8 out of 10, Good, (473)
"Very pleasant place to stay"
The price is S$210
includes taxes & fees
3 Jul - 4 Jul
The Armon Stamford Hotel & Conference

Super 8 by Wyndham Stamford/New York City Area

2.5 star property
6.2 out of 10, (1002)
"It feels very good and comfortable!"
The price is S$148
includes taxes & fees
13 Jul - 14 Jul
Super 8 by Wyndham Stamford/New York City Area

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

3.0 star property
6.6 out of 10, (575)
"It was nice, and the breakfast was good. I loved the little diner attached to the hotel. The elevator was a bit sketchy, but the room was clean, and I slept well."
The price is S$128
includes taxes & fees
27 Jul - 28 Jul
La Quinta Inn & Suites by Wyndham Stamford / New York City

Ethan Allen Hotel

3.5 star property
7.8 out of 10, Good, (1014)
"Nice staff, good location, dog friendly."
The price is S$174
includes taxes & fees
2 Jul - 3 Jul
Ethan Allen Hotel

Hyatt Regency Greenwich

4.0 star property
8.2 out of 10, Very good, (956)
"Great stay!"
The price is S$245
includes taxes & fees
20 Jul - 21 Jul
Hyatt Regency Greenwich

Maron Hotel And Suites

2.5 star property
7.4 out of 10, Good, (1010)
"Very nice place"
Maron Hotel And Suites

J House Greenwich

4.0 star property
9.0 out of 10, Wonderful, (1003)
"Great amenities - spa, pool, valet parking, etc. "
J House Greenwich

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

2.5 star property
9.0 out of 10, Wonderful, (152)
"Substantial breakfast, large rooms, comfy bed, clean, accommodating staff!"
The price is S$177
includes taxes & fees
13 Jul - 14 Jul
Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG

Springhill Suites By Marriott - Danbury

3.0 star property
9.0 out of 10, Wonderful, (780)
"Great place to stay in the middle of antique shopping meca and close to great restaurants and bars. "
The price is S$191
includes taxes & fees
3 Jul - 4 Jul
Springhill Suites By Marriott - Danbury

Hotel Zero Degrees Danbury

4.0 star property
9.0 out of 10, Wonderful, (1006)
"Great staff and very comfortable surroundings!"
The price is S$220
includes taxes & fees
3 Jul - 4 Jul
Hotel Zero Degrees Danbury
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.
Save an average of 15% on thousands of hotels when you're signed in

Pet-friendly hotels in Ossining you'll enjoy

These family-friendly hotels in Ossining may fit your trip

Check out hotels with a pool in Ossining

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.

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.

Photo by Linda Zanetti
Open Photo by Linda Zanetti

Frequently asked questions

Where is the best place to stay in Ossining?

Baymont by Wyndham White Plains - Elmsford, located 6.8 mi (10.9 km) from the heart of Ossining, is a top choice for your stay, based on our traveller data. Other good options for your visit to the area are Amsterdam Hotel and Hilltop Inn & Suites. See all available top hotels, or vacation rentals in Ossining.

What are some of the best holiday rentals that Ossining has to offer?

3BR Prime Luxury near NYC w Arcade Room: This holiday home rental outside Ossining is near the airport and offers free WiFi to help you feel perfectly comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind. 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. Features daily, an indoor pool and complimentary high-speed (wired) Internet access. Hyatt Regency Greenwich and Armoni Inn & Suites 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. A top sight in the area is Woodbury Common Premium Outlets. In Ossining, there are 9 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 Teatown Lake Reservation, Merchants Square 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.