Ossining Holidays
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Ossining Flight & Hotel Packages
Price found within the past 48 hours. Click for updated prices.
OYO Times Square
Manhattan
S$1,395
per person
2 Nov - 8 Nov
found 1 day ago
Return direct flight included
London (LON) to New York (JFK)
6.8/10 (2,082 reviews)
I was really disappointed with our stay here. The staff was hardly helpful. A couple were pleasant to talk to but made hardly any effort to help us. Most of the seating downstairs had large stains on them. The room was super basic and either someone left some travel size products in the shower that weren’t cleaned out or they just had random brands left in the shower. It all just felt unprofessional. We will not be staying here again.
Reviewed on 25 Sept, 2026
Radio Hotel
Manhattan
S$1,403
per person
2 Nov - 8 Nov
found 1 day ago
Return direct flight included
London (LON) to New York (JFK)
8.6/10 Excellent! (2,455 reviews)
Cute lobby but restaurant was closed several mornings for maintenance. "Destination fee" a poor value.
Shower did not drain properly and leaked all over the floor into the bedroom, thankfully everything is concrete so no mildew. Sink set up strangely such that you cannot brush your teeth or wash your face without getting water all over the floor.
Friendly staff. Great pillows.
Reviewed on 25 Sept, 2026
Top hotels in Ossining
Windrose On Hudson
1 Shady Lane Farm Road Ossining NY
Fully refundableReserve now, pay when you stay
S$303
27 Sept - 28 Sept
includes taxes & fees
8.6/10 Excellent! (246 reviews)
"The hotel was lovely. It must have been a truly impressive estate back in the day. The public spaces are renovated so beautifully. The room had so much natural light with the floor to ceiling windows, the beds were quite comfortable and the bathroom had everything we needed. I just wish I could have ..."
Reviewed on 25 Sept, 2026
Tarrytown House Estate
49 E Sunnyside Lane Tarrytown NY
S$274
27 Sept - 28 Sept
includes taxes & fees
Armoni Inn & Suites
329 Route 303 Orangeburg NY
6.2/10 (2,267 reviews)
"Nothing worked. Complete overhaul needed."
Reviewed on 7 Sept, 2026
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.
Stay near popular Ossining attractions
Travelers Rest
This historic former stagecoach stop serves exceptional American and German cuisine in elegant, fireplace-lit dining rooms. Stroll through the landscaped gardens with waterfalls before your memorable meal.
Photo by louann ohora
Teatown Lake Reservation
This 1,000-acre nature preserve features diverse ecosystems along scenic trails. Explore the floating boardwalk across the lake for wildlife viewing and see the island's native wildflower collection.
Hudson Hills Golf Course
Nestled in Ossining's rolling terrain, this Mark Mungeam-designed course challenges players with strategic bunkers and undulating fairways. Enjoy Hudson River Valley views while navigating the thoughtful 18 holes.
Sing Sing Prison Museum
Step inside America's most infamous prison at the Sing Sing Prison Museum, opening in 2025 for its 200th anniversary. Explore artefacts and stories illuminating incarceration and rehabilitation in America.
Kitchawan Preserve
Explore the great outdoors at Kitchawan Preserve, a lovely green space in Ossining. Amble around this quaint area's riverfront and enjoy its top-notch restaurants.
Ossining Historical Society
This intimate museum preserves Ossining's heritage through artefacts connected to Sing Sing Prison and local history. Schedule a personalised appointment for the most enriching exploration of this community treasure.
Louis Engel Waterfront Park
Louis Engel Waterfront Park is just one of the places to see in Ossining, so why not enjoy the other things to explore during your travels? Amble around this quaint area's riverfront and enjoy its top-notch restaurants.
Merchants Square
9.0/10 (2 reviews)
Explore the great outdoors at Merchants Square, a lovely green space in Ossining. Stroll along the riverfront or attend a sporting event in this quaint area.
Frequently asked questions
How much does an Ossining holiday package cost?
You can snap up a holiday package to this popular destination from S$1,395 on Expedia. However, how much your holiday 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 holiday packages? Try to avoid visiting during public holidays and any major festivals.
How many days is enough for Ossining?
To fully enjoy your Ossining holiday, we recommend staying for 5 days. Divide your time between visiting Teatown Lake Reservation, Kitchawan Preserve and other top attractions, in addition to experiencing neighbourhoods like Town of Mount Pleasant and Pleasantville. If you've got some time to spare, add a tour or day trip to your Ossining holiday itinerary.
Is it worth booking a holiday package to Ossining?
Ossining has everything you need for an unforgettable escape. Get your Ossining holiday 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 holiday package well in advance.
Is it cheaper to book an Ossining holiday as a package?
You can enjoy significant savings on your Ossining retreat by booking a personalised holiday 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 holiday 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?
- 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.
- Budget wisely: Besides the price of your accommodation, 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.
- 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.
- Bundle your accommodation and airfare: After you've settled on your dates and duration, lock in the ideal Ossining holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
