Ossining Vacation Packages 2025/2026 from $358

Ossining flight + hotel vacation packages

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

Somerset Hills Hotel, Tapestry Collection by Hilton

Save 100% on your flight

$358

per person

Nov 15 - Nov 18

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. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. A terrace, a garden, and a snack bar/deli are also on offer.

1 Hotel Brooklyn Bridge

$1,568

per person

Nov 17 - Nov 22

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

A full-service spa, a gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Enjoy the seasonal outdoor pool and visit the 2 bars/lounges and poolside bar for drinks.

The Inn At Fox Hollow Hotel

Save 100% on your flight

$378

per person

Nov 4 - Nov 7

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

This hotel features 2 bars/lounges, a poolside bar, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free train station pick-up. Enjoy the 24-hour gym and perks like free self parking and a free area shuttle.

1 Hotel Central Park

Manhattan

$1,933

per person

Nov 13 - Nov 18

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 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.

Hotel Seville Nomad, in the Unbound Collection by Hyatt

Manhattan

Save 100% on your flight

$923

per person

Dec 17 - Dec 23

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 free WiFi in public areas, express check-out, and valet parking. A computer station, dry cleaning, and luggage storage are also on offer.

Top Ossining hotels deals

Windrose On Hudson

1 Shady Lane Farm Road, Ossining, NY

Free Cancellation

$230 total

per night

Nov 5 - Nov 6

This hotel features a gym and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A coffee shop is provided and the front desk is staffed around-the-clock.

Parking included

Free WiFi

Armoni Inn & Suites

329 Route 303, Orangeburg, NY

Free Cancellation

Reserve now, pay when you stay

$109 total

per night

Oct 6 - Oct 7

This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, limo/town car service, and a grocery/convenience store are also offered.

Pool

Parking included

Royal Regency Hotel

165 Tuckahoe Rd, Yonkers, NY

Free Cancellation

Reserve now, pay when you stay

$150 total

per night

Oct 26 - Oct 27

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

Hampton Inn White Plains/Tarrytown

200 West Main Street, Elmsford, NY

Free Cancellation

Reserve now, pay when you stay

$145 total

per night

Oct 26 - Oct 27

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

Amsterdam Hotel

19 Clarks Hill Ave, Stamford, CT

Free Cancellation

Reserve now, pay when you stay

$127 total

per night

Nov 2 - Nov 3

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. There's a gym on site, and a 24-hour front desk and a terrace are also provided.

Breakfast included

Parking included

La Quinta Inn & Suites by Wyndham Stamford / New York City

135 Harvard Avenue, Stamford, CT

Free Cancellation

Reserve now, pay when you stay

$95 total

per night

Oct 26 - Oct 27

This hotel features a restaurant, an indoor pool, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Pool

Breakfast 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 quaint 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 quaint 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 $358. 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.