Ossining Vacations from NT$49,854

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The Latest Ossining Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hampton Inn Manhattan/Times Square South

Hampton Inn Manhattan/Times Square South

2.5 out of 5
Manhattan
per person
Sep 26 - Sep 30
found 13 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to New York (JFK)
7.4/10 Good! (1,722 reviews)
The man running breakfast was wonderful! He made the mornings bright with his genuine smile and warmth. The front desk staff were also friendly and welcoming. We felt bad for the housekeeping staff however. They were extremely limited in their ability to do their job since they had to share the elevators with the guests. There were only 2 (tiny) elevators in the entire hotel which didn't even support the number of guests, let alone the housekeeping staff as well. Waiting for extended periods of time for an elevator was common. We resorted to using the stairs many times even though we stayed on the 25th floor. However, the location was great, close proximity to many restaurants, bars, and entertainment.

Reviewed on 2025/8/17

Hilton Club The Quin New York

Hilton Club The Quin New York

5 out of 5
Manhattan
per person
Sep 26 - Sep 30
found 13 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to New York (JFK)
9.4/10 Exceptional! (1,161 reviews)
Best neighborhood. Easy access to everything. 24/7 supermarket with great food options.

Reviewed on 2025/8/17

Pendry Manhattan West

Pendry Manhattan West

5 out of 5
Manhattan
Save 100% on your flight
per person
Sep 26 - Sep 30
found 13 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to New York (JFK)
9.8/10 Exceptional! (437 reviews)
We had such a wonderful stay at Pendry Manhattan West. The hotel is absolutely beautiful—exquisite, tasteful, blissfully quiet, and impeccably clean. Our corner suite was truly impressive, with expansive windows wrapping around the room and offering breathtaking views in multiple directions across Manhattan. The luxurious bath and modern, refined design made it a serene retreat after a full day exploring the city. A special mention goes to Oksana, the director/manager, whose attentiveness and genuine care made us feel so welcomed. She handled everything with such thoughtfulness and professionalism that we left feeling truly valued as guests. Her warmth and dedication left a lasting impression on us. The location couldn’t be more convenient—right outside Penn Station—making travel logistics effortless. From the elegant design to the exceptional service, our experience here was nothing short of perfect, and we will absolutely be returning. Highly recommend!

Reviewed on 2025/8/10

The Ritz-Carlton New York, Central Park

The Ritz-Carlton New York, Central Park

5 out of 5
Manhattan
per person
Sep 26 - Sep 30
found 13 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to New York (JFK)
9.2/10 Wonderful! (489 reviews)
We recently stayed at the Ritz for my wife's 40th birthday, and we were not disappointed! Their attention to details was impeccable, the kid friendly check-in (kids actually have their own check-i

Reviewed on 2025/8/16

The Algonquin Hotel Times Square, Autograph Collection

The Algonquin Hotel Times Square, Autograph Collection

4 out of 5
Manhattan
per person
Sep 26 - Sep 30
found 13 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to New York (JFK)
8.8/10 Excellent! (1,003 reviews)
The Front Desk and Restaurant and Bell staffs are all so efficient and friendly and our room was made up nicely everyday.

Reviewed on 2025/8/9

Find the Best Ossining Vacation Packages

Ossining Hotel Deals

Windrose On Hudson

Windrose On Hudson

2 out of 5
1 Old Albany Post Rd, Ossining, NY
Fully refundableReserve now, pay when you stay
The price is NT$6,569 per night from Aug 19 to Aug 20
NT$6,569
NT$7,316 total
Aug 19 - Aug 20
includes taxes & fees
8.2/10 Very Good! (9 reviews)
"Only one night so did not use the amenities. The refrigerator in the room died in the night so lost my leftovers. The room was clean and the staff was helpful. The shower function was strange. I would stay there again."

Reviewed on 2025/8/12

Windrose On Hudson
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 NT$3,799 per night from Sep 1 to Sep 2
NT$3,799
NT$4,345 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (1,111 reviews)
"Location great for access to Tarrytown train. Clean and friendly."

Reviewed on 2025/8/14

Hampton Inn White Plains/Tarrytown
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 NT$4,309 per night from Aug 24 to Aug 25
NT$4,309
NT$4,928 total
Aug 24 - Aug 25
includes taxes & fees
8.2/10 Very Good! (1,394 reviews)
"N/A"

Reviewed on 2025/8/9

Baymont by Wyndham White Plains - Elmsford
See all 1,221 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.

Discover the most popular places to visit in Ossining

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

Sing Sing Prison Museum

You can spend time browsing the exhibits at Sing Sing Prison Museum during your travels in Ossining. Amble around this quaint area's riverfront and enjoy its top-notch restaurants.

Sing Sing Prison Museum

Hudson Hills Golf Course

Enjoy a round of golf in Ossining at Hudson Hills Golf Course. Amble around this quaint area's riverfront and enjoy its top-notch restaurants.

Hudson Hills Golf Course

Frequently asked questions

How much does an Ossining vacation package cost?
You can snap up a vacation package to this popular destination from NT$49,854 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 many days is enough for Ossining?
To fully enjoy your Ossining vacation, we recommend staying for 5 days. Divide your time between visiting Teatown Lake Reservation, Kitchawan Preserve and other top attractions, in addition to experiencing neighborhoods like Town of Mount Pleasant and Pleasantville. If you've got some time to spare, add a tour or day trip to your Ossining vacation itinerary.
Is it worth booking a vacation package to Ossining?
Ossining has everything you need for an unforgettable escape. Get your Ossining vacation off to a flying start by visiting top attractions like Louis Engel Waterfront Park.
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.

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