Ossining Holidays from NZ$749

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The Latest Ossining Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Interfaith 21
Courtyard New York Manhattan/ Midtown East
Hotel Riu Plaza New York Times Square
Hotel Riu Plaza Manhattan Times Square
PUBLIC, an Ian Schrager hotel

Ossining Holiday

Our pick of the best Ossining Hotel Deals

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 NZ$225 per night from 27 July to 28 July
NZ$225
27 July - 28 July
includes taxes & fees
8.2/10 Very Good! (2,145 reviews)
"Friendly staff and clean room. Very nice place to stay."

Reviewed on 17 Jul. 2025

Royal Regency Hotel
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 NZ$293 per night from 24 July to 25 July
NZ$293
24 July - 25 July
includes taxes & fees
8.2/10 Very Good! (1,382 reviews)
"Ants on the night stand. Very nice entry pool and lobby. Go up to and level then walk aways to another elevator to the actual hotel. My room looked ok at first then i realized it was an old hotel reno that was looking very tired. Didn’t seem to clean. Felt very disappointed for the price!"

Reviewed on 15 Jul. 2025

Baymont by Wyndham White Plains - Elmsford
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 NZ$263 per night from 27 July to 28 July
NZ$263
27 July - 28 July
includes taxes & fees
7.8/10 Good! (1,062 reviews)
Not the best, but acceptable.
"Check-in and out was super easy. Room initially had an odor that reduced during our stay. Bathroom not super clean. Decided not to use the shower."

Reviewed on 13 Jul. 2025

Hampton Inn White Plains/Tarrytown
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.

Discover the most popular places to visit in Ossining

Frequently asked questions

How much does an Ossining holiday package cost?
You can snap up a holiday package to this popular destination from NZ$749 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.

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