Ossining Vacations from ₩1,050,586

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The Latest Ossining Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Price was ₩1,497,050, price is now ₩1,050,586 per person
₩1,050,586
per person
Dec 20 - Dec 24
found 17 hours ago
Roundtrip non-stop flight included
Nashville (BNA) to New York (JFK)
8.8/10 Excellent! (8,157 reviews)
Clean rooms, excellent location, and great customer service. This is my second time at this location and I will absolutely stay here again!

Reviewed on Nov 1, 2026

The William Hotel Midtown, New York

The William Hotel Midtown, New York

3.5 out of 5
Manhattan
Save 100% on your flight
Price was ₩2,345,235, price is now ₩1,567,858 per person
₩1,567,858
per person
Dec 20 - Dec 24
found 17 hours ago
Roundtrip non-stop flight included
Nashville (BNA) to New York (JFK)
9.4/10 Exceptional! (275 reviews)
Perfect location

Reviewed on Oct 30, 2026

42 Hotel

42 Hotel

3.5 out of 5
Price was ₩1,573,588, price is now ₩1,188,662 per person
₩1,188,662
per person
Dec 20 - Dec 24
found 17 hours ago
Roundtrip non-stop flight included
Nashville (BNA) to New York (JFK)
9/10 Wonderful! (1,005 reviews)
We were visiting Brooklyn for the first time and this was a perfect spot for us. The staff were friendly and helpful. The room was clean, and on arrival I asked for a quiet room and they accommodated my request with no hesitation. The rooms come with complimentary water, wine, coffee and chocolates as well as lovely lotions and if you need anything else it’s a phone call away. We were able to walk into Williamsburg and feel safe with no issues and lots of great coffee shops and cafes on the way. We will be coming back!

Reviewed on Nov 1, 2026

Hotel Seville Nomad, in the Unbound Collection by Hyatt

Hotel Seville Nomad, in the Unbound Collection by Hyatt

4.5 out of 5
Manhattan
Price was ₩1,663,138, price is now ₩1,268,128 per person
₩1,268,128
per person
Dec 20 - Dec 24
found 17 hours ago
Roundtrip non-stop flight included
Nashville (BNA) to New York (JFK)
8.8/10 Excellent! (1,570 reviews)

Ace Hotel New York

Ace Hotel New York

4 out of 5
Manhattan
Price was ₩1,581,244, price is now ₩1,213,556 per person
₩1,213,556
per person
Dec 20 - Dec 24
found 17 hours ago
Roundtrip non-stop flight included
Nashville (BNA) to New York (JFK)
8.2/10 Very Good! (1,208 reviews)
Our room was clean, but not super comfortable or well maintained. The soap dispensers were falling off the wall in the shower and the bathroom floor was very slippery. Not a lot of functional counter space and towel hooks and racks were in inconvenient spots in relation to the shower. Mattress was a little uncomfortable. The room itself was kind of vibey if a little dated. Overall, not dissatisfied, but may look elsewhere next time. Great location in nomad, though. Easy access to lots of subway lines.

Reviewed on Oct 31, 2026

Find the Best Ossining Vacation Packages

Ossining Hotel Deals

Windrose On Hudson

Windrose On Hudson

3 out of 5
1 Shady Lane Farm Road Ossining NY
Fully refundableReserve now, pay when you stay
The price is ₩201,578 per night from Nov 15 to Nov 16
₩201,578
₩224,507 total
Nov 15 - Nov 16
includes taxes & fees
8.6/10 Excellent! (277 reviews)
"Hotel amenities (bar, restaurants) were not open to guests, only private parties. Rooms are dated and metal doors in the bathrooms are rusting through. Beds are as hard as a board. No air circulation, no water provided or coffee maker. Check in staff gave a family members key to someone else."

Reviewed on Nov 1, 2026

Windrose On Hudson
LIV Hotel Bronx - Newly Built

LIV Hotel Bronx - Newly Built

3 out of 5
3530 Webster Ave Bronx NY
Fully refundableReserve now, pay when you stay
The price is ₩186,971 per night from Nov 8 to Nov 9
₩186,971
₩219,219 total
Nov 8 - Nov 9
includes taxes & fees
7.2/10 Good! (1,227 reviews)
"Love the location"

Reviewed on Nov 1, 2026

LIV Hotel Bronx - Newly Built
Royal Regency Hotel

Royal Regency Hotel

3.5 out of 5
165 Tuckahoe Rd Yonkers NY
Fully refundableReserve now, pay when you stay
The price is ₩151,273 per night from Nov 8 to Nov 9
₩151,273
₩184,796 total
Nov 8 - Nov 9
includes taxes & fees
Royal Regency Hotel
See all 1,273 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.

Stay near popular Ossining attractions

A dam with a reservoir, surrounded by autumn foliage and hills.

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.
See properties

Frequently asked questions

How much does an Ossining vacation package cost?
You can snap up a vacation package to this popular destination from ₩1,050,586 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.