Ossining Vacations

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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 ₩315,275 per night from Jul 19 to Jul 20
₩315,275
₩351,116 total
Jul 19 - Jul 20
includes taxes & fees
8.6/10 Excellent! (180 reviews)
"Overall, my stay was pleasant, but there were a few areas that impacted my experience. If you're looking for standard hotel amenities such as an in-room coffee maker, microwave, mini refrigerator, or a larger television, this property may not meet those expectations. Unfortunately, I was initially ..."

Reviewed on Jul 4, 2026

Windrose On Hudson
Armoni Inn & Suites

Armoni Inn & Suites

3.5 out of 5
329 Route 303 Orangeburg NY
Fully refundableReserve now, pay when you stay
The price is ₩131,724 per night from Jul 6 to Jul 7
₩131,724
₩146,685 total
Jul 6 - Jul 7
includes taxes & fees
6/10 (2,271 reviews)
"if all you want to do is sleep - this place will pass . the window AC works . the bed is standard and clean. The check in process was easy. Other than that I can’t give a good"

Reviewed on Jul 5, 2026

Armoni Inn & Suites
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 ₩194,213 per night from Jul 12 to Jul 13
₩194,213
₩222,146 total
Jul 12 - Jul 13
includes taxes & fees
8/10 Very Good! (1,540 reviews)
"The property is old/dated/in poor repair totally unlike any other Hampton Inn that I have stayed at. My ac unit was squeaking and when I called the front desk to see if we could change rooms the front desk told me to stay in the same room because if I switched to another room the ac may not work ..."

Reviewed on Jul 4, 2026

Hampton Inn White Plains/Tarrytown
See all 1,336 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 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.