Ossining Vacation Packages 2025 from $549

Ossining flight + hotel vacation packages

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

Ace Hotel New York

Manhattan

Save 100% on your flight

per person

Aug 22 - Aug 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

This hotel features 2 coffee shops/cafes and a 24-hour gym. Enjoy a meal from the restaurant and perks like free WiFi. A bar/lounge, a 24-hour front desk, and express check-out are also provided.

1 Hotel Brooklyn Bridge

per person

Sep 8 - Sep 14

found 12 hours ago

Roundtrip flight included

Dallas (DFW) 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.

Harpoon House

Save 100% on your flight

per person

Aug 24 - Aug 27

found 1 day ago

Roundtrip non-stop flight included

Los Angeles (LAX) to New York (JFK)

This bed & breakfast features a restaurant and 3 bars/lounges. Guests will appreciate free perks like free self parking and WiFi in public areas. A coffee shop, a terrace, and a garden are also on offer.

The Fifty Sonesta Hotel New York

Manhattan

Save 100% on your flight

per person

Aug 22 - Aug 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New York (JFK)

A 24-hour gym, valet parking, and laundry facilities are featured at this hotel. Traveling on business? Take advantage of the business center and WiFi in public areas. A snack bar/deli, a lobby fireplace, and express check-in are also on offer.

Ruschmeyers Hotel

Save 100% on your flight

per person

Aug 24 - Aug 27

found 1 day ago

Roundtrip non-stop flight included

Los Angeles (LAX) to New York (JFK)

A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area, express check-in, and express check-out are also on offer.

Top Ossining hotels deals

Baymont by Wyndham White Plains - Elmsford

540 Saw Mill River Rd, Elmsford, NY

Free Cancellation

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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

Hilltop Inn & Suites

125 Tuckahoe Rd, Yonkers, NY

Free Cancellation

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A gym is featured at this hotel, along with free self parking. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A computer station is provided and the front desk is staffed around-the-clock.

Breakfast included

Parking included

Hyatt Place New York/Yonkers

7000 Mall Walk, Yonkers, NY

Free Cancellation

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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. Guests will appreciate freebies like buffet breakfast and free self parking.

Breakfast included

Pet friendly

Ardsley Acres Hotel Westchester

560 Saw Mill River Rd, Ardsley, NY

Free Cancellation

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Free self parking is available and the hotel's front desk is staffed around-the-clock. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A garden and a picnic area are also provided.

Breakfast included

Parking included

Amsterdam Hotel

19 Clarks Hill Ave, Stamford, CT

Free Cancellation

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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

Hyatt Regency Greenwich

1800 E Putnam Avenue, Old Greenwich, CT

Free Cancellation

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This smoke-free hotel includes 2 restaurants, an indoor pool, and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. Self parking, a coffee shop, and a snack bar/deli are also offered.

Pool

Pet friendly

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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 $549. 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.