Ossining Vacation Packages 2025/2026 from $225

Ossining flight + hotel vacation packages

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

Holiday Inn Express & Suites Woodside LaGuardia Airport by IHG

Queens

Save 100% on your flight

$225

per person

Jan 30 - Feb 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (NYC)

A restaurant and a 24-hour gym are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the free buffet breakfast each morning.

Radio Hotel

Manhattan

$318

per person

Feb 12 - Feb 15

found 17 hours ago

Roundtrip flight included

Atlanta (ATL) to New York (NYC)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Valet parking, a coffee shop, and a snack bar/deli are also offered.

Kimpton Theta New York - Times Square by IHG

Manhattan

Save 100% on your flight

$400

per person

Jan 22 - Jan 27

found 8 hours ago

Roundtrip flight included

Atlanta (ATL) to New York (NYC)

A restaurant and a 24-hour gym are featured at this hotel. WiFi in public areas is free. Valet parking, a coffee shop, and express check-out are also offered.

Fouquet's New York

Manhattan

$818

per person

Jan 29 - Feb 1

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (NYC)

A full-service spa, 2 restaurants, and an indoor pool are all featured at this luxury hotel. Enjoy the 24-hour gym and perks like free WiFi. You'll appreciate the steam room, bar/lounge, and concierge services.

The Shelburne Sonesta New York

Manhattan

Save 100% on your flight

$225

per person

Feb 6 - Feb 9

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (NYC)

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center, laundry service, and valet parking. WiFi in public areas, luggage storage, and laundry facilities 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

$146 nightly

$163 total

Nov 30 - Dec 1

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

$135 nightly

$155 total

Nov 30 - Dec 1

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

Sonesta White Plains Downtown

66 Hale Ave White Plains NY

Free Cancellation

Reserve now, pay when you stay

$174 nightly

$199 total

Dec 18 - Dec 19

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.

Ramada by Wyndham Bronx

1000 Baychester Ave Bronx NY

Free Cancellation

Reserve now, pay when you stay

$122 nightly

$143 total

Nov 23 - Nov 24

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

Royal Regency Hotel

165 Tuckahoe Rd Yonkers NY

Free Cancellation

Reserve now, pay when you stay

$102 nightly

$120 total

Dec 18 - Dec 19

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.

Hampton Inn White Plains/Tarrytown

200 West Main Street Elmsford NY

Free Cancellation

Reserve now, pay when you stay

$127 nightly

$145 total

Nov 30 - Dec 1

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.

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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 family-friendly area's riverfront and enjoy its top-notch restaurants.

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.

Thomas J. Watson Research Center

Learn about the local history of Ossining with a stop at Thomas J. Watson Research Center. Stroll along the riverfront in this family-friendly area, or check out 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 $225. 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.