Ossining Vacations from AED5,112

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The Latest Ossining Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel 57 by LuxUrban

Hotel 57 by LuxUrban

4 out of 5
Manhattan
per person
Jun 8 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Abu Dhabi (AUH) to New York (JFK)
8.2/10 Very Good! (1,634 reviews)
The staff members were absolutely fantastic at every interaction! Would stay again for their great attitudes and assistance alone, truly a home away from home kinda feel to it :)

Reviewed on 17 April 2025

The Lexington Hotel, Autograph Collection

The Lexington Hotel, Autograph Collection

4 out of 5
Manhattan
per person
Jun 8 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Abu Dhabi (AUH) to New York (JFK)
8.4/10 Very Good! (1,217 reviews)
Old facility but well maintained. Small space in room but very clean. The staff are very nice, and corrected room assignment mistake very quickly and nicely. It was a surprise to charge a fee for short time luggage storage.

Reviewed on 19 April 2025

PUBLIC, an Ian Schrager hotel

PUBLIC, an Ian Schrager hotel

4 out of 5
Manhattan
per person
Jun 8 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Abu Dhabi (AUH) to New York (JFK)
8.2/10 Very Good! (2,806 reviews)
Beautiful hotel. Great location.

Reviewed on 19 April 2025

Elegant Harlem Suites

Elegant Harlem Suites

2 out of 5
Manhattan
per person
Jun 8 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Abu Dhabi (AUH) to New York (JFK)
No reviews
Hard Rock Hotel New York

Hard Rock Hotel New York

4.5 out of 5
Manhattan
per person
Jun 8 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Abu Dhabi (AUH) to New York (JFK)
9.4/10 Exceptional! (4,144 reviews)
The food was overpriced and did not taste nice.

Reviewed on 20 April 2025

Find the Best Ossining Vacation Packages

Ossining Hotel Deals

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 AED 434 per night from Apr 27 to Apr 28
AED 434
AED 496 total
includes taxes & fees
27 Apr - 28 Apr
8.2/10 Very Good! (1,290 reviews)
"It is a nice property my 2nd stay there"

Reviewed on 17 April 2025

Baymont by Wyndham White Plains - Elmsford
Hampton Inn & Suites Yonkers
Hampton Inn & Suites Yonkers
2.5 out of 5
160 Corporate Blvd, Yonkers, NY
Fully refundableReserve now, pay when you stay
The price is AED 434 per night from Apr 27 to Apr 28
AED 434
AED 511 total
includes taxes & fees
27 Apr - 28 Apr
8/10 Very Good! (1,356 reviews)
"Perfect coming here again with my children."

Reviewed on 18 April 2025

Hampton Inn & Suites Yonkers
Amsterdam Hotel
Amsterdam Hotel
2 out of 5
19 Clarks Hill Ave, Stamford, CT
Fully refundableReserve now, pay when you stay
The price is AED 364 per night from Apr 21 to Apr 22
AED 364
AED 422 total
includes taxes & fees
21 Apr - 22 Apr
8.4/10 Very Good! (1,579 reviews)
"The room was nice. The only issue was the hot water gave out once."

Reviewed on 18 April 2025

Amsterdam Hotel
See all 1,154 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 vacation package cost?
You can snap up a vacation package to this popular destination from AED5,112 on Expedia. However, how much your vacation to Ossining costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Ossining?
The off-season is the best time to head to Ossining if you’re hoping to keep costs down. Another tip for scoring cheap Ossining vacation packages? Try to avoid visiting during public holidays and any major festivals.
How to find the best Ossining package deals?
Use Expedia’s handy filters to find some tempting Ossining package deals. When you start your search, just set your maximum budget and then sort the results by “Price: low to high.” If you want to save, plan your adventure for midweek, or look for Ossining package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it’s usually best to book your vacation package well in advance.
Is it cheaper to book an Ossining vacation as a package?
You can enjoy significant savings on your Ossining retreat by booking a personalized vacation package. Click on the “Package” heading, then select your travel dates and destination to view some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Ossining?
If you have your Ossining travel dates locked in, book as early as you can to grab some incredible deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are great for impromptu escapes.
How to plan a trip to Ossining?

  1. Pick the best time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to travel to Ossining.
  2. Budget wisely: Besides the price of your accommodations, you’ll need to consider other expenses too. These include transportation, food and flights. Also, set aside some extra funds for unexpected expenses that may arise during your trip to Ossining.
  3. Set the duration of your trip: Start by listing all the attractions and activities you’d like to get to in Ossining. Then, estimate how long you’ll need at each, including any travel time.
  4. Bundle your accommodations and airfare: After you’ve settled on your dates and duration, lock in the ideal Ossining vacation package for you.

Discover the most popular places to visit in Ossining

Lovely spot in Westchester, NY

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

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

Thomas J. Watson Research Center

Learn about the local history of Ossining with a stop at Thomas J. Watson Research Center. Stroll along the riverfront in this quaint area, or check out its top-notch restaurants.

Thomas J. Watson Research Center