Ossining Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Linda Zanetti

Top hotels in Ossining

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 5.740.428 ₫ per night from 10 Aug to 11 Aug
5.740.428 ₫
6.393.400 ₫ total
10 Aug - 11 Aug
includes taxes & fees
8/10 Very Good! (7 reviews)
"Staying the historic former GE Crottonville training center. The place is amazing. It wasn’t intended to be a hotel per se. It is way, way more than that. I think it is still looking for its footing as a hotel/corporate conference training center for public, so being able to stay here feels like ..."

Reviewed on 3 Aug 2025

Windrose On Hudson
Armoni Inn & Suites

Armoni Inn & Suites

3.5 out of 5
329 Route 303, Orangeburg, NY
The price is 1.889.623 ₫ per night from 2 Sept to 3 Sept
1.889.623 ₫
2.104.568 ₫ total
2 Sept - 3 Sept
includes taxes & fees
6/10 (1,981 reviews)
Nice last-minute booking
"It was your basic last minute motel booking nice enough to spend the night if you have to clean rooms despite the outside of appearance, but don’t make it your first pick restaurant closed bar closed, but on the high side pool is beautiful and open and open late."

Reviewed on 28 Jul 2025

Armoni Inn & Suites
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 3.765.354 ₫ per night from 17 Aug to 18 Aug
3.765.354 ₫
4.306.624 ₫ total
17 Aug - 18 Aug
includes taxes & fees
8.2/10 Very Good! (1,389 reviews)
"Super comfy bed breakfast was great"

Reviewed on 7 Aug 2025

Baymont by Wyndham White Plains - Elmsford
See all 1,208 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.

Popular places to visit

Teatown Lake Reservation

Teatown Lake Reservation

Explore the great outdoors at Teatown Lake Reservation, a lovely green space in Ossining. Amble around this quaint area's riverfront and enjoy its top-notch restaurants.

Teatown Lake Reservation

Thomas J. Watson Research Center

Learn about the local history of Ossining when you take a trip to Thomas J. Watson Research Center. Stroll along the riverfront in this quaint area or visit its top-notch restaurants.

Thomas J. Watson Research Center

Travelers Rest

After visiting Travelers Rest, make a plan to see the other sights and activities in Ossining. Amble around the area's parks or visit its monuments.

Travelers Rest

Frequently asked questions

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

  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 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.
  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 accommodation and airfare: After you've settled on your dates and duration, lock in the ideal Ossining holiday package for you.