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.
Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was $972, price is now $512 per person
$512
per person
May 20 - May 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a snack bar/deli are also offered.
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was $1,622, price is now $788 per person
$788
per person
May 20 - May 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
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.
NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Price was $1,730, price is now $909 per person
$909
per person
May 1 - May 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
A restaurant and a rooftop terrace are featured at this hotel. WiFi in public areas is free. A business center, a terrace, and luggage storage are also on offer.
Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
Price was $1,122, price is now $590 per person
$590
per person
May 20 - May 24
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.

Top Ossining hotels deals

Windrose On Hudson

Windrose On Hudson

3 out of 5
1 Shady Lane Farm Road Ossining NY
Free Cancellation
Reserve now, pay when you stay
$172 nightly
The price is $191 total per night
$191 total
Mar 1 - Mar 2
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.
Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

2.5 out of 5
540 Saw Mill River Rd Elmsford NY
Free Cancellation
Reserve now, pay when you stay
$130 nightly
The price is $148 total per night
$148 total
Mar 1 - Mar 2
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like self-serve breakfast and free self parking.
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

4 out of 5
425 E Route 59 Nanuet NY
Free Cancellation
Reserve now, pay when you stay
$106 nightly
The price is $123 total per night
$123 total
Mar 22 - Mar 23
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.
Pool
Hot Tub
LIV Hotel Bronx

LIV Hotel Bronx

3 out of 5
3530 Webster Ave Bronx NY
Free Cancellation
Reserve now, pay when you stay
$116 nightly
The price is $137 total per night
$137 total
Mar 1 - Mar 2
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.
Royal Regency Hotel

Royal Regency Hotel

3.5 out of 5
165 Tuckahoe Rd Yonkers NY
Free Cancellation
Reserve now, pay when you stay
$113 nightly
The price is $133 total per night
$133 total
Mar 29 - Mar 30
Total with taxes and fees
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Breakfast included
Parking included
Ramada by Wyndham Bronx

Ramada by Wyndham Bronx

3 out of 5
1000 Baychester Ave Bronx NY
Free Cancellation
Reserve now, pay when you stay
$135 nightly
The price is $159 total per night
$159 total
Mar 2 - Mar 3
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. A snack bar/deli, a grocery/convenience store, and a lobby fireplace are also on offer.
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

Lovely spot in Westchester, NY

Teatown Lake Reservation

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

Teatown Lake Reservation
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

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 $512. 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.
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