Ossining Holidays from £877

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Your Ossining Holiday

Experience the energy and excitement of Ossining with a tailor-made Ossining holiday package. From its rich history to its spectacular views and beyond, you'll never have a boring moment in this city. Eager to explore your surroundings? Tarrytown Music Hall, Van Cortlandt Manor and Sing Sing Correctional Facility are some of the leading places to visit during a trip to Ossining. Browse Expedia's extensive range of travel options and begin planning your perfect holiday to Ossining now.

Top Ossining Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Clark - Newark Area by IHG

Holiday Inn Clark - Newark Area by IHG

3 out of 5
Madison Hill
per person
6 Oct - 9 Oct
found 1 day ago
Return flight included
London (LON) to Newark Liberty Intl. Airport (EWR)
8.4/10 Very Good! (1,000 reviews)
The bed seems old and worn out. Bathroom is small. Overall though everything was good

Reviewed on 4 Aug 2025

Holiday Inn Express Newark Airport Elizabeth by IHG

Holiday Inn Express Newark Airport Elizabeth by IHG

2.5 out of 5
per person
6 Oct - 9 Oct
found 1 day ago
Return flight included
London (LON) to Newark Liberty Intl. Airport (EWR)
8.6/10 Excellent! (1,654 reviews)
It took 45+ to get extra pillows….sucks when you have a early flight

Reviewed on 3 Aug 2025

Holiday Inn Express And Suites Bronx NYC by IHG

Holiday Inn Express And Suites Bronx NYC by IHG

2.5 out of 5
per person
6 Oct - 9 Oct
found 1 day ago
Return flight included
London (LON) to New York (JFK)
8.4/10 Very Good! (310 reviews)
The room was nice, The staff was nice but the area and the fact that there was NO parking made it uncomfortable parking my vehicle 6 blocks away.

Reviewed on 5 Aug 2025

Crowne Plaza Newark Airport by IHG

Crowne Plaza Newark Airport by IHG

3.5 out of 5
per person
6 Oct - 9 Oct
found 1 day ago
Return flight included
London (LON) to Newark Liberty Intl. Airport (EWR)
7.8/10 Good! (2,274 reviews)
The check in Lady may have had her teeth out recently, as she never smiled once. I felt i was an inconvenience to her day. Not a good Corporate image.Everything else about the Hotel was very good.

Reviewed on 5 Aug 2025

Holiday Inn Hasbrouck Heights-Meadowlands by IHG

Holiday Inn Hasbrouck Heights-Meadowlands by IHG

3 out of 5
per person
6 Oct - 9 Oct
found 1 day ago
Return flight included
London (LON) to Newark Liberty Intl. Airport (EWR)
8.6/10 Excellent! (1,039 reviews)
Staff was really nice and friendly.

Reviewed on 5 Aug 2025

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

Top hotels in Ossining

Windrose On Hudson

Windrose On Hudson

2 out of 5
1 Old Albany Post Rd, Ossining, NY
The price is £188 per night from 6 Aug to 7 Aug
£188
6 Aug - 7 Aug
includes taxes & fees
8/10 Very Good! (7 reviews)
"Staying the historic former GE Crottonville training center. The place is amazing. It wasn’t intended to be a hotel per se. It is way, way more than that. I think it is still looking for its footing as a hotel/corporate conference training center for public, so being able to stay here feels like ..."

Reviewed on 3 Aug 2025

Windrose On Hudson
Armoni Inn & Suites

Armoni Inn & Suites

3.5 out of 5
329 Route 303, Orangeburg, NY
The price is £60 per night from 2 Sept to 3 Sept
£60
2 Sept - 3 Sept
includes taxes & fees
6/10 (1,984 reviews)
Nice last-minute booking
"It was your basic last minute motel booking nice enough to spend the night if you have to clean rooms despite the outside of appearance, but don’t make it your first pick restaurant closed bar closed, but on the high side pool is beautiful and open and open late."

Reviewed on 28 Jul 2025

Armoni Inn & Suites
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 £124 per night from 17 Aug to 18 Aug
£124
17 Aug - 18 Aug
includes taxes & fees
8.2/10 Very Good! (1,390 reviews)
"The rooms were large & bright. Bathroom too- Had elevator. Nice breakfast area. Great value for the money no matter part of country that we choose a Baymont Hotel."

Reviewed on 4 Aug 2025

Baymont by Wyndham White Plains - Elmsford
See all 1,205 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
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Frequently asked questions

How much does an Ossining travel package cost?
Get your credit card ready, because a trip to Ossining starts from only £877. 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.

* 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.