Ossining Holidays from £988

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Your Ossining Holiday

Renowned for its rich history and spectacular views, Ossining is a fabulous getaway destination. Lock in one of our Ossining holiday packages and experience all that this fascinating city has to offer. If your trip to Ossining includes a little sightseeing, drop by famous attractions like Van Cortlandt Manor, Tarrytown Music Hall and Sleepy Hollow Cemetery. Whoever you're taking time off with and whatever you want to spend, your dream Ossining holiday is just a few clicks away with Expedia.

The Latest Ossining Holiday Deals

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
28 Jun - 5 Jul
Return flight included
Edinburgh (EDI) to New York (JFK)
8.8/10 Excellent! (3,722 reviews)
Breakfast was great quiet room, convenience for the place,

Reviewed on 17 Apr 2024

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
per person
28 Jun - 2 Jul
Return direct flight included
London (LON) to New York (JFK)
8.6/10 Excellent! (1,000 reviews)
Nothing short of Amazing

Reviewed on 17 Apr 2024

RIU Plaza Manhattan Times Square

RIU Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
22 Jun - 27 Jun
Return flight included
Edinburgh (EDI) to New York (JFK)
9/10 Wonderful! (3,013 reviews)
Small rooms but easy parking ( on weekday )

Reviewed on 15 Apr 2024

The William Vale

The William Vale

5 out of 5
Save 100% on your flight
per person
24 May - 26 May
Return flight included
London (LON) to New York (JFK)
8.6/10 Excellent! (1,003 reviews)
Great rooms gotham balcony amazing view

Reviewed on 13 Apr 2024

The Westin New York Grand Central

The Westin New York Grand Central

4.5 out of 5
Manhattan
per person
27 May - 31 May
Return flight included
Edinburgh (EDI) to New York (JFK)
8.8/10 Excellent! (2,314 reviews)
Good staff. Very clean property. Good amenities. Comfortable bed. Clean rooms.

Reviewed on 14 Apr 2024

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Save 100% on your flight
per person
5 Jun - 10 Jun
Return flight included
Edinburgh (EDI) to New York (JFK)
9.8/10 Exceptional! (1,001 reviews)
Very clean, quiet, and convenient. Every staff member I interacted with was exceptionally friendly!

Reviewed on 14 Apr 2024

Prices and availability subject to change. Additional terms may apply.

Ossining Essential Information

Language
English
Currency
U.S dollars
Closest Airport
LaGuardia Airport (LGA)
Population
25,400
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Bear Mountain State Park, Franklin D. Roosevelt State Park and Paramount Hudson Valley Theatre

Our pick of the best Ossining Hotel Deals

Armoni Inn & Suites
Armoni Inn & Suites
3.5 out of 5
329 Route 303, Orangeburg, NY
Stay at this business-friendly hotel in Orangeburg. Enjoy free WiFi, free parking and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
6/10 (1,025 reviews)
"The woman who checked me in was very nice."

Reviewed on 14 Apr 2024

Armoni Inn & Suites
Royal Regency Hotel
Royal Regency Hotel
3.5 out of 5
165 Tuckahoe Rd, Yonkers, NY
Stay at this business-friendly hotel in Yonkers. Enjoy free breakfast, free WiFi and free parking. Our guests praise the breakfast and the helpful staff in their ...
8/10 Very Good! (1,389 reviews)
"Very clean and modern."

Reviewed on 16 Apr 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
Stay at this business-friendly hotel in Elmsford. Enjoy free breakfast, free WiFi and free parking. Our guests praise the breakfast and the helpful staff in ...
8/10 Very Good! (1,004 reviews)
"Room is spacious. Breakfast was good."

Reviewed on 18 Apr 2024

Baymont by Wyndham White Plains - Elmsford
See all 1,017 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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does an Ossining travel package cost?
Get your credit card ready, because a trip to Ossining starts from only £988. When you bundle your hotels, flights and car rentals into a travel package, you’ll land the biggest bargains.
If I'm not able to travel, can I cancel my Ossining travel package?
Yes, you can. We understand that even the best-laid plans can go awry, so we’re happy to help if you have to make changes to your Ossining travel package. You may be able to cancel or change your itinerary for free if you’ve booked within 24 hours. Your airline, hotel or car rental company may impose a fee if your booking was made more than 24 hours ago. Visit our Customer Service Portal for further information. Also, check your itinerary for the finer details on change fees.
How do I get a cheap travel package to Ossining?
Booking a flight and hotel together with Expedia won’t just save precious time — it’ll save you cash too. An Ossining travel package makes it a breeze to create the ideal trip. With more than 550 airlines throughout the world to pick from, finding convenient flights that suit your busy schedule won’t be a challenge. Not only that, we’ve got over 1,000,000 properties globally to choose from. Talk about choice! No matter who you are, Expedia puts the world within your reach.
Does Expedia offer Book Now, Pay Later Ossining holidays?
Good news! We do. Expedia has partnered with online lender Klarna to help you easily pay for your trip in instalments. Simply click on the payment plan best suited to your needs during the checkout process and take away the stress of budgeting for your trip. Be sure to bundle your accommodation, flights and car hire with Expedia to get the biggest bang for your buck. Browse our flexible payment options below:

  • Pay monthly holidays: If paying bite-sized amounts each month works for you, Klarna can help. Paying in convenient monthly instalments will make your holiday dreams come true.
  • Pay in instalments holidays: If you’d like to pay for your escape across multiple transactions, holidays paid in instalments might be right for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the full total upfront) makes it easier to hit that “book now” button, go for a low deposit holiday payment plan from Klarna.

Where should I stay in Ossining?
You’ll want to stay where the action is. Many travellers favor hotels in the vicinity of popular sights, such as Van Cortlandt Manor, Thomas J. Watson Research Centre and Sing Sing Correctional Facility.
What are the top hotels in Ossining?
Make a reservation at Baymont by Wyndham White Plains - Elmsford. It’s one of this neighbourhood’s most popular properties. Another highly rated option in Ossining is Courtyard by Marriott Yonkers Westchester County.
How far in advance should I book my Ossining holiday?
It all depends on the air carrier, but you can generally compare international fares on Expedia up to a year in advance. While it’s advisable to book ahead of time, lucky customers occasionally score a cheaper seat only weeks before the date of departure.
What does an Expedia Ossining travel package include?
Rental cars, flights and hotels, or any combination of the three — it’s your pick! Whether you’re headed to Ossining with the entire family or travelling solo, there’s a package to fit your style and budget. Once you’ve made your booking, why not add on some tours and experiences?
What should I know before booking an Ossining travel package?
When you book your hotels, flights and car rentals together, you’ll enjoy great discounts. Whether you’re organising an island getaway in a villa or want to stay in a cosy apartment in the city, Expedia can help make it happen.
Can I choose my airline with an Ossining Expedia travel package?
You can, and with more than 550 airlines to select from around the world, you have plenty of choice. Take a look at the available options and see which airline suits your needs and budget.

Discover the most popular places to visit in Ossining

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 family-friendly 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 quaint area's riverfront and enjoy its top-notch restaurants.

Sing Sing Prison Museum

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.