Ossining Holidays from £717

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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.
Tarrytown House Estate on the Hudson

Tarrytown House Estate on the Hudson

3.5 out of 5
Save 100% on your flight
per person
6 Sept - 13 Sept
found 9 hours ago
Return flight included
Manchester (MAN) to White Plains (HPN)
8/10 Very Good! (1,002 reviews)
Everything was great, but I hope the outdoor pool can stay open until 7:00 or 8:00 during the summer. Since check-in time is at 4:00, and the outdoor pool closes at 6:00, there’s really not enough time to enjoy it. Even though there’s an indoor pool, I still prefer the outdoor one.

Reviewed on 4 Jul 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
per person
24 Aug - 30 Aug
found 1 day ago
Return direct flight included
Glasgow (GLA) to New York (JFK)
8.8/10 Excellent! (1,004 reviews)
One of the Best hotel I have ever stayed. Little small, little pricey, but they did everything right.

Reviewed on 25 Jun 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Save 100% on your flight
per person
16 Aug - 23 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to New York (JFK)
9.8/10 Exceptional! (1,212 reviews)
I've stayed in a lot of good quality hotels in New York,but this one was a bit different. My stay felt very safe and personable, I had everything I needed, and if I didn't I had the front desk to always guide me through any questions I had. Very clean rooms, and such an amazing surrounding area with lots of options for food

Reviewed on 2 Jul 2025

The St. Regis New York

The St. Regis New York

5 out of 5
Manhattan
Save 100% on your flight
per person
16 Aug - 23 Aug
found 23 hours ago
Return direct flight included
Glasgow (GLA) to New York (JFK)
9/10 Wonderful! (230 reviews)
Service in the hotel was terrible , butler service and room service was very bad

Reviewed on 11 Jun 2025

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Save 100% on your flight
per person
16 Aug - 23 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to New York (JFK)
9/10 Wonderful! (1,001 reviews)
We love Loews Regency NYC. The staff is exceptional and the rooms are very comfortable.

Reviewed on 29 Jun 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

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 £120 per night from 6 Jul to 7 Jul
£120
6 Jul - 7 Jul
includes taxes & fees
8.2/10 Very Good! (1,366 reviews)
"Very clean"

Reviewed on 4 Jul 2025

Baymont by Wyndham White Plains - Elmsford
Hampton Inn White Plains/Tarrytown
Hampton Inn White Plains/Tarrytown
3 out of 5
200 West Main Street, Elmsford, NY
Fully refundableReserve now, pay when you stay
The price is £106 per night from 13 Jul to 14 Jul
£106
13 Jul - 14 Jul
includes taxes & fees
7.8/10 Good! (1,051 reviews)
"Very nice staff facility dated in some areas."

Reviewed on 3 Jul 2025

Hampton Inn White Plains/Tarrytown
Hilltop Inn & Suites
Hilltop Inn & Suites
2.5 out of 5
125 Tuckahoe Rd, Yonkers, NY
Fully refundableReserve now, pay when you stay
The price is £92 per night from 15 Jul to 16 Jul
£92
15 Jul - 16 Jul
includes taxes & fees
6.8/10 (258 reviews)
"the property is outdated, there are no modern (usb, etc) connections. the TV system is also old, the furniture is old. but for the price its a good deal. the AC works well, the staff is not bothersome, the place is quiet except for the occasional ghetto clients that want to spend all day with their ..."

Reviewed on 1 Jul 2025

Hilltop Inn & Suites
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

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 £717. 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.