Ossining 2024 Holidays

Photo by Linda Zanetti
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Top Flight + Hotel Deals in Ossining

Price found within the past 48 hours. Click for updated prices.
Ace Hotel New York

Ace Hotel New York

4 out of 5
Manhattan
per person
5 Jul - 8 Jul
Return direct flight included
Dublin (DUB) to New York (JFK)
8.2/10 Very Good! (1,002 reviews)
Location was good but the room was too small

Reviewed on 14 May 2024

The Westin New York Grand Central

The Westin New York Grand Central

4.5 out of 5
Manhattan
per person
5 Jul - 8 Jul
Return direct flight included
Dublin (DUB) to New York (JFK)
8.8/10 Excellent! (2,376 reviews)
Our entire stay was fantastic! All of our requests were answered within minutes. The hotel was very clean and safe. The hotel restaurant had very good food and drinks.

Reviewed on 14 May 2024

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
per person
5 Jul - 8 Jul
Return direct flight included
Dublin (DUB) to New York (JFK)
8.8/10 Excellent! (3,686 reviews)
Property was very clean, staff very helpful, good choice at breakfast

Reviewed on 13 May 2024

RIU Plaza Manhattan Times Square

RIU Plaza Manhattan Times Square

4 out of 5
Manhattan
per person
5 Jul - 8 Jul
Return direct flight included
Dublin (DUB) to New York (JFK)
9/10 Wonderful! (3,068 reviews)
Included breakfast was amazing

Reviewed on 12 May 2024

Park Lane New York

Park Lane New York

4.5 out of 5
Manhattan
per person
5 Jul - 8 Jul
Return direct flight included
Dublin (DUB) to New York (JFK)
8.6/10 Excellent! (822 reviews)
Beautiful hotel in great location across from Central Park. The rooms are spacious and very comfortable with nice amenities in the bathroom. The only little couple of things were that the wifi isn't great, it would be nice to see QTips and cotton swabs in the bathroom and of course a coffee/Nespresso machine for the room. I get that they want people to pay for coffee downstairs but for almost $800 a night that begins to feel very nickely-dimey of them. Overall an excellent place to stay

Reviewed on 13 May 2024

Top hotels in Ossining

Armoni Inn & Suites
Armoni Inn & Suites
3.5 out of 5
329 Route 303, Orangeburg, NY
Fully refundableReserve now, pay when you stay
The price is €63 per night from 22 May to 23 May
€63
per night
22 May - 23 May
6/10 (1,100 reviews)
"Food"

Reviewed on 11 May 2024

Armoni Inn & Suites
Royal Regency Hotel
Royal Regency Hotel
3.5 out of 5
165 Tuckahoe Rd, Yonkers, NY
Fully refundableReserve now, pay when you stay
The price is €186 per night from 21 May to 22 May
€186
per night
21 May - 22 May
8/10 Very Good! (1,458 reviews)
"Very beautiful place"

Reviewed on 14 May 2024

Royal Regency Hotel
Baymont by Wyndham White Plains - Elmsford
Baymont by Wyndham White Plains - Elmsford
2.5 out of 5
540 Saw Mill River Rd, Elmsford, NY
Fully refundableReserve now, pay when you stay
The price is €135 per night from 27 May to 28 May
€135
per night
27 May - 28 May
8/10 Very Good! (1,014 reviews)
"Always clean. Good breakfast, rates are good"

Reviewed on 13 May 2024

Baymont by Wyndham White Plains - Elmsford
See all 1,031 properties 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.

Frequently asked questions

How much does an Ossining holiday package cost?
Customize your Ossining package from just €762. Pick from any combination of flights, hotels and rental cars to create the trip of your dreams. Remember to add on one or two experiences!
How do I get a cheap travel package to Ossining?
Combine your flights and hotels, add extras such as activities, and save with an Ossining holiday package. You won’t just pick up superb discounts on your adventure — you’ll have plenty of choice within your reach too. When you book with Expedia, you can choose from more than 550 partner airlines and 1,000,000 properties all over the world. Your next grand adventure starts right here, right now!
Where should I stay in Ossining?
A trip to Ossining isn’t complete without seeing Van Cortlandt Manor, Sing Sing Correctional Facility and Croton Point Park. Spend your evenings close to these popular sights and make sightseeing a breeze.
What are the top hotels in Ossining?
Neighbour’s House - Welcome is one of Ossining’s leading hotels. Book a room here and you can slumber peacefully knowing you’re in capable hands.
How far in advance should I book my Ossining holiday?
It depends on the airline, but it’s usually possible to compare international flights on Expedia nearly a year in advance. While it’s advisable to book ahead of time, lucky customers will occasionally score a cheaper ticket just weeks before departure dates.
What does an Expedia Ossining travel package include?
It comes down to what you’re looking for. If you’re travelling by yourself, you might decide to combine flights and hotels. Taking the whole family to Ossining? A travel package including rental cars, flights and hotels might suit you better. Expedia gives you the flexibility to tailor your travel package.
What should I know before booking an Ossining travel package?
We already have low prices. However, you’ll snap up even more bargains when you book your hotels, flights and car rentals together. With an Expedia travel package, you’ll get transparent pricing and a terrific range of choice.
Can I choose my airline with an Ossining Expedia holiday package?
Yes, and with more than 550 airlines to pick from globally, you have loads of choice. Have a look through the available options and find out which airline best fits your needs and budget.
If I'm not able to travel, can I cancel my Ossining holiday package?
Your situation can change in the blink of an eye, so yes. You may be able to cancel and rebook your Ossining holiday package for free within 24 hours of booking. For older bookings, you can still make the necessary changes, but your car rental company, hotel or airline may impose a charge. Need more information? Have a look at our Customer Service Portal. We’re here to help make sure your getaway goes off without a hitch.

Popular places to visit

Image for Teatown Lake Reservation

Teatown Lake Reservation

Explore the great outdoors at Teatown Lake Reservation, a lovely green space in Ossining. Amble around this family-friendly area's riverfront and enjoy its top-notch restaurants.

Teatown Lake Reservation
Image for Sing Sing Correctional Facility

Sing Sing Correctional Facility

After visiting Sing Sing Correctional Facility, make a plan to see the other sights and activities in Ossining. Amble around this quaint area's riverfront and enjoy its top-notch restaurants.

Sing Sing Correctional Facility
Image for Sing Sing Prison Museum

Sing Sing Prison Museum

You can enjoy some culture when you stop by Sing Sing Prison Museum in Ossining. Amble around this family-friendly area's riverfront and enjoy its top-notch restaurants.

Sing Sing Prison Museum

More trip options

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.