Ossining Vacation Packages 2026 from $409

Ossining flight + hotel vacation packages

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

Delta Hotels by Marriott Woodbridge

$409

per person

Jun 5 - Jun 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)

This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and perks like free self parking and a free area shuttle.

Seven Beach Lane

$1,154

per person

Jun 7 - Jun 12

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Newark Liberty Intl. Airport (EWR)

This hotel features a restaurant and 2 bars/lounges. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. A garden, luggage storage, and concierge services are also on offer.

Topping Rose House

$1,542

per person

Jun 7 - Jun 12

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Newark Liberty Intl. Airport (EWR)

A full-service spa, an outdoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and free valet parking. Enjoy the gym and perks like free self parking and a free area shuttle.

Hotel St. James

Manhattan

Save 100% on your flight

$432

per person

May 21 - 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.

1 Hotel Central Park

Manhattan

Save 100% on your flight

$1,099

per person

May 21 - May 25

found 1 day ago

Roundtrip non-stop 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 24-hour business center, free WiFi in public areas, and valet parking. A coffee shop, limo/town car service, and a snack bar/deli are also on offer.

Top Ossining hotels deals

Windrose On Hudson

1 Shady Lane Farm Road Ossining NY

Free Cancellation

Reserve now, pay when you stay

$172 nightly

$191 total

May 3 - May 4

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

Baymont by Wyndham White Plains - Elmsford

540 Saw Mill River Rd Elmsford NY

Free Cancellation

Reserve now, pay when you stay

$123 nightly

$141 total

Apr 26 - Apr 27

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.

Pool

Breakfast included

LIV Hotel Bronx - Newly Built

3530 Webster Ave Bronx NY

Free Cancellation

Reserve now, pay when you stay

$143 nightly

$168 total

Apr 19 - Apr 20

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 & Suites Yonkers

160 Corporate Blvd Yonkers NY

Free Cancellation

Reserve now, pay when you stay

$122 nightly

$144 total

Apr 27 - Apr 28

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. Enjoy the free buffet breakfast each morning.

Breakfast included

Pet friendly

Royal Regency Hotel

165 Tuckahoe Rd Yonkers NY

Free Cancellation

Reserve now, pay when you stay

$107 nightly

$126 total

Apr 26 - Apr 27

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

1000 Baychester Ave Bronx NY

Free Cancellation

Reserve now, pay when you stay

$135 nightly

$159 total

Apr 19 - Apr 20

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.

Breakfast included

Parking included

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

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.

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.

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.

Frequently asked questions

How much are vacation packages to Ossining?

You can pick up an excellent hotel and flight bundle for as low as $409. 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.