Ossining Vacation Packages 2026/2026 from $235

Ossining flight + hotel vacation packages

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

The Gallivant Times Square

Manhattan

Save 100% on your flight

$235

per person

Feb 19 - Feb 22

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (NYC)

A restaurant and a gym are featured at this hotel. There's a computer station and multilingual staff can provide around-the-clock assistance.

INNSiDE by Meliá New York Nomad

Manhattan

$322

per person

Feb 5 - Feb 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (NYC)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A terrace, limo/town car service, and a picnic area are also on offer.

Sheraton New York Times Square Hotel

Manhattan

Save 100% on your flight

$306

per person

Feb 12 - Feb 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

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

Manhattan

Save 100% on your flight

$459

per person

Feb 12 - Feb 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (NYC)

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.

JW Marriott Essex House New York

Manhattan

Save 100% on your flight

$636

per person

Feb 5 - Feb 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A bar/lounge, a 24-hour front desk, and a convenience store are also provided.

Top Ossining hotels deals

Windrose On Hudson

1 Shady Lane Farm Road Ossining NY

Free Cancellation

Reserve now, pay when you stay

$188 nightly

$209 total

Dec 14 - Dec 15

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

$125 nightly

$143 total

Jan 4 - Jan 5, 2026

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

$178 nightly

$203 total

Jan 4 - Jan 5, 2026

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 Regency Hotel

165 Tuckahoe Rd Yonkers NY

Free Cancellation

Reserve now, pay when you stay

$107 nightly

$126 total

Dec 7 - Dec 8

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

DoubleTree by Hilton Hotel Nanuet

425 E Route 59 Nanuet NY

Free Cancellation

Reserve now, pay when you stay

$98 nightly

$114 total

Jan 4 - Jan 5, 2026

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

Ramada by Wyndham Bronx

1000 Baychester Ave Bronx NY

Free Cancellation

Reserve now, pay when you stay

$134 nightly

$158 total

Jan 5 - Jan 6, 2026

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

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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 quaint 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 $235. 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.