Ossining Packages (Flight + Hotel)

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Top Ossining Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Outsite Chelsea

Outsite Chelsea

2 out of 5
Manhattan
per person
28 Jul - 3 Aug
found 1 day ago
Return direct flight included
Helsinki (HEL) to New York (JFK)
10/10 Exceptional! (1 review)
Everything was so perfect! Location was walkable to meatpacking district, staff onsite to clean daily, and other guests were friendly. 10/10 recommend!

Reviewed on 21 May 2025

Hotel 1080 Brooklyn

Hotel 1080 Brooklyn

3.5 out of 5
per person
28 Jul - 3 Aug
found 1 day ago
Return direct flight included
Helsinki (HEL) to New York (JFK)
7.6/10 Good! (289 reviews)
The lady at the front desk was the best

Reviewed on 22 Jun 2025

EVEN Hotel Brooklyn by IHG

EVEN Hotel Brooklyn by IHG

4 out of 5
per person
28 Jul - 3 Aug
found 1 day ago
Return direct flight included
Helsinki (HEL) to New York (JFK)
8.6/10 Excellent! (1,390 reviews)
The property is well located and clean, staff was nice. Room was very small and had a damaged fold down desk that we couldn’t put back up. Totally fine for a quick stay but some of the aesthetics were a little tacky.

Reviewed on 22 Jun 2025

Truss Hotel Times Square

Truss Hotel Times Square

4 out of 5
Manhattan
per person
28 Jul - 3 Aug
found 1 day ago
Return direct flight included
Helsinki (HEL) to New York (JFK)
8.2/10 Very Good! (2,669 reviews)
The front desk staff was great! They all greeted us every time we came in or out. They also offered us bottled water. The location was perfect for our first trip to NYC. It put us right in the middle of everything we wanted to do. The room though small, which we expected in NYC, was clean and the beds were comfortable. The only issue we had was the TV would connect to the internet but they fixed it. The highlight of our stay was Luce at the front desk. She was so kind and gracious. One evening after my families' dinner we talk for quite a while about what my family had done and about her experience as a NY local. She was a gem! Take care of her and don't let her go!

Reviewed on 23 Jun 2025

Hotel 27 by LuxUrban

Hotel 27 by LuxUrban

2.5 out of 5
Manhattan
per person
28 Jul - 3 Aug
found 1 day ago
Return direct flight included
Helsinki (HEL) to New York (JFK)
7.6/10 Good! (796 reviews)
I return yearly to this location however this time the tv didn’t work and I was just left to deal with it…..

Reviewed on 23 Jun 2025

Top hotels in Ossining

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 ฿5,128 per night from 29 Jun to 30 Jun
฿5,128
฿5,865 total
29 Jun - 30 Jun
includes taxes & fees
8.2/10 Very Good! (1,356 reviews)
"Close to WMC, excellent service, helpful staff"

Reviewed on 20 Jun 2025

Baymont by Wyndham White Plains - Elmsford
Amsterdam Hotel
Amsterdam Hotel
2 out of 5
19 Clarks Hill Ave, Stamford, CT
Fully refundableReserve now, pay when you stay
8.4/10 Very Good! (1,596 reviews)
Set Reasonable Expectations
"The Amsterdam Hotel was an extremely cost-effective option in Stamford, where the average hotel rates have skyrocketed. That said, set your expectations accordingly. This is a dated hotel with old furnishings and no frills (although the included continental breakfast was a nice extra). However, the ..."

Reviewed on 20 Jun 2025

Get rates
Amsterdam Hotel
Hilltop Inn & Suites
Hilltop Inn & Suites
2.5 out of 5
125 Tuckahoe Rd, Yonkers, NY
Fully refundableReserve now, pay when you stay
The price is ฿3,360 per night from 25 Jun to 26 Jun
฿3,360
฿3,956 total
25 Jun - 26 Jun
includes taxes & fees
6.8/10 (236 reviews)
"Nice place"

Reviewed on 20 Jun 2025

Hilltop Inn & Suites
See all 1,207 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.

Frequently asked questions

How much does an Ossining holiday package cost?
You can snap up a holiday package to this popular destination from ฿38,141 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.