Ossining Vacations

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Find the Best Ossining Vacation Packages

Ossining Hotel Deals

Windrose On Hudson

Windrose On Hudson

1 Shady Lane Farm Road Ossining NY
Fully refundableReserve now, pay when you stay
₩266,947
₩297,313 total
Aug 24 - Aug 25
includes taxes & fees
Windrose On Hudson
Tarrytown House Estate

Tarrytown House Estate

49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
₩223,850
₩291,231 total
Aug 11 - Aug 12
includes taxes & fees
8.2/10 Very Good! (1,232 reviews)
"Breakfast would have cost us $30 each....so we did not eat there. That's ridiculous. The room was clean. However, be ready to walk to the building your room is in. There are different buildings..it was confusing at first...no elevators, so idk if they have specific buildings for that. The grounds ..."

Reviewed on Aug 10, 2026

Tarrytown House Estate
Royal Regency Hotel

Royal Regency Hotel

165 Tuckahoe Rd Yonkers NY
Fully refundableReserve now, pay when you stay
₩171,055
₩208,455 total
Aug 30 - Aug 31
includes taxes & fees
Royal Regency Hotel
See all 1,304 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.
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A misty lake surrounded by trees with sunlight filtering through the leaves.
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.
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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 family-friendly area's riverfront and enjoy its top-notch restaurants.
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Ossining Public Library

Learn about the local history of Ossining when you spend time at Ossining Public Library. Amble around the area's parks or visit its monuments.
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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 artifacts and stories illuminating incarceration and rehabilitation in America.
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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.
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Depot Square

This charming community space sits adjacent to Ossining's Metro-North station, offering a peaceful urban retreat. Enjoy a moment of calm on the benches before exploring nearby local eateries or catching your train.
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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.
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Frequently asked questions

How much does an Ossining vacation package cost?
You can snap up a vacation package to this popular destination 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.

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