Deals on vacations and trips to Ossining

Save when you book Ossining package deals

Choose two or more items and save on your trip:

Ossining flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Price was $1,116, price is now $518 per person
$518
per person
Aug 19 - Aug 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
Free WiFi in public areas, a library, and luggage storage are available at this hotel. Multilingual staff at the 24-hour front desk can provide around-the-clock assistance.
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was $1,611, price is now $822 per person
$822
per person
Aug 19 - Aug 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
This hotel features a restaurant, a gym, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the free buffet breakfast each morning.
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was $1,495, price is now $767 per person
$767
per person
Aug 19 - Aug 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
This property features a restaurant, a gym, and a bar/lounge. WiFi in public areas is free. A snack bar/deli, dry cleaning, and luggage storage are also on offer.
Dream Hotel Bronx

Dream Hotel Bronx

2 out of 5
South Side
Save 100% on your flight
Price was $1,452, price is now $747 per person
$747
per person
Jul 14 - Jul 18
found 9 hours ago
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
Free WiFi in public areas is provided and the front desk is staffed around-the-clock.
Arthouse Hotel New York City

Arthouse Hotel New York City

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,215, price is now $638 per person
$638
per person
Aug 13 - Aug 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
This smoke-free hotel features 2 restaurants, a bar/lounge, and a gym. Business travelers can take advantage of the 24-hour business center. Self parking, a library, and a computer station are also offered.

Top Ossining hotels deals

Windrose On Hudson

Windrose On Hudson

3 out of 5
1 Shady Lane Farm Road Ossining NY
$206 nightly
The price is $230 total per night
$230 total
Jun 21 - Jun 22
Total with taxes and fees
This hotel features a gym and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, a coffee shop, and luggage storage are also offered.
Parking included
Free WiFi
Sonesta White Plains Downtown

Sonesta White Plains Downtown

4 out of 5
66 Hale Ave White Plains NY
Free Cancellation
Reserve now, pay when you stay
$198 nightly
The price is $226 total per night
$226 total
Jun 14 - Jun 15
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Enjoy the 24-hour gym and perks like free airport pick-up.
Pool
Free airport shuttle
Royal Hotel Bronx

Royal Hotel Bronx

2 out of 5
3362 Boston Road Bronx NY
$111 nightly
The price is $131 total per night
$131 total
Jun 7 - Jun 8
Total with taxes and fees
Free WiFi in public areas is provided and the front desk is staffed around-the-clock.
Free WiFi
Air conditioning
Hyatt Regency Greenwich

Hyatt Regency Greenwich

4 out of 5
1800 E Putnam Avenue Old Greenwich CT
Free Cancellation
Reserve now, pay when you stay
$212 nightly
The price is $244 total per night
$244 total
Jun 28 - Jun 29
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an indoor pool, and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. There's a bar/lounge on site, and concierge services and wedding services are also provided.
Pool
Pet friendly
LIV Hotel Bronx - Newly Built

LIV Hotel Bronx - Newly Built

3 out of 5
3530 Webster Ave Bronx NY
Free Cancellation
Reserve now, pay when you stay
$143 nightly
The price is $168 total per night
$168 total
Jun 7 - Jun 8
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. The front desk is staffed around-the-clock and concierge services are on offer.
Parking included
Free WiFi
Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

3 out of 5
200 West Main Street Elmsford NY
Free Cancellation
Reserve now, pay when you stay
$112 nightly
The price is $129 total per night
$129 total
Jul 2 - Jul 3
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the express check-in and free internet in public areas. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.
Breakfast included
Pet friendly
Don't see what you're looking for?
See all available properties in Ossining
View all properties
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

Rest stop area beside interstate highway where travelers rest and sight see Tioga Reservoir and Dam in Pennsylvania New York state border

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
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

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.

Sing Sing Correctional Facility

Frequently asked questions

How much are vacation packages to Ossining?
You can pick up an excellent hotel and flight bundle for as low as $518. With a Travelocity vacation package, a getaway in Ossining has never looked more irresistible! Save your time and cash and then get a head start on packing those bags.
Where can I get the best vacation package deals for Ossining?
Travelocity can help you snag an awesome Ossining package deal. With as many as 400 airlines and 1,000,000 properties worldwide, there's no doubt you'll find the perfect mix.
Why should I purchase my Ossining vacation bundle via Travelocity?
By booking your hotel, flights, activities and car rental altogether, you'll save both time and money. We have round-the-clock customer support, and you'll know that you'll always be getting the best deal possible with our Price Match Guarantee. So, what's stopping you? Book the vacation of your dreams today and start packing!
Will I save money on my Ossining car rental if I combine it with a hotel or flight?
Absolutely — combine your hotel, flight and car into an Ossining vacation package and you can save a handsome sum. With so much to discover in the Ossining area, having your own wheels will make exploring easy. Once you're behind the wheel, hit the wide open road and head to Statue of Liberty, a renowned sight approximately 35 mi from Ossining.
Which airport is best for Ossining?
John F. Kennedy Intl. Airport (JFK) is one of the most popular airports in Ossining. It's around 35 mi south of the buzzing city center. Other choices include Liberty Intl. Airport (EWR) (35 mi away from central Ossining) and LaGuardia Airport (LGA) (25 mi away from central Ossining).
What is there to do in Ossining?
You'll notice an undeniable magic as you stroll the streets of Ossining. Thomas J. Watson Research Center and Louis Engel Waterfront Park are just a couple of attractions that make this city such a sought-after destination, so put them at the top of your list of places to see.
Where should I stay when visiting Ossining?
Many people check in to the 7BR Winter Beacon Retreat: Jacuzzi, BBQ, Games!. It's sure to be a great base for your Ossining escape.

Photos of local treasures

Browse Ossining vacation photos for more inspiration

Boardwalk over marshland on the trail at Teatown Lake Reservation in Ossining, New York.
Westchester, NY, USA: A rail bridge spans an inlet on the Hudson River, with St. Augustine’s Roman Catholic Church, Ossining, NY, in the background.
The start of the Bergmann boardwalk at Teatown Reservation in Westchester County, New York
rows of Victorian building sit t side by side in downtown Ossining, New York
Ossining