Ossining Vacation Packages 2026 from $503

Ossining flight + hotel vacation packages

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

Hotel Riu Plaza Manhattan Times Square

Manhattan

Save 100% on your flight

$503

per person

Sep 10 - Sep 12

found 1 day ago

Roundtrip flight included

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

This hotel 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.

2 bedroom luxury Empire State VIEW

Manhattan

$1,527

per person

Jul 28 - Jul 31

found 1 day ago

Roundtrip flight included

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

Night Hotel Broadway

Manhattan

Save 100% on your flight

$545

per person

Jul 25 - Jul 31

found 1 day ago

Roundtrip flight included

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

A steam room is featured at this hotel, along with free WiFi in public areas and dry cleaning. There's luggage storage and multilingual staff can provide around-the-clock assistance.

Hotel Riu Plaza New York Times Square

Manhattan

Save 100% on your flight

$531

per person

Sep 10 - Sep 12

found 1 day ago

Roundtrip flight included

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

This hotel features a restaurant, a gym, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the free buffet breakfast each morning.

The Towers at Lotte New York Palace

Manhattan

Save 100% on your flight

$1,470

per person

Aug 7 - Aug 11

found 1 day ago

Roundtrip flight included

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

This hotel features a restaurant, a gym, and a bar/lounge. Families will appreciate the onsite laundry facilities and in-room childcare. Guests will appreciate perks like free WiFi and a free area shuttle.

Top Ossining hotels deals

Windrose On Hudson

1 Shady Lane Farm Road Ossining NY

Free Cancellation

Reserve now, pay when you stay

$185 nightly

$207 total

Jun 21 - Jun 22

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.

Baymont by Wyndham White Plains - Elmsford

540 Saw Mill River Rd Elmsford NY

Free Cancellation

Reserve now, pay when you stay

$137 nightly

$157 total

Jun 30 - Jul 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.

Tarrytown House Estate

49 E Sunnyside Lane Tarrytown NY

Free Cancellation

Reserve now, pay when you stay

$163 nightly

$186 total

Jun 28 - Jun 29

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the gym and perks like free self parking.

Royal Hotel Bronx

3362 Boston Road Bronx NY

$97 nightly

$115 total

Jun 16 - Jun 17

Total with taxes and fees

Free WiFi in public areas is provided and the front desk is staffed around-the-clock.

Hyatt Regency Greenwich

1800 E Putnam Avenue Old Greenwich CT

Free Cancellation

Reserve now, pay when you stay

$212 nightly

$244 total

Jun 28 - Jun 29

Total with taxes and fees

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. There's a bar/lounge on site, and concierge services and wedding services are also provided.

Hampton Inn White Plains/Tarrytown

200 West Main Street Elmsford NY

Free Cancellation

Reserve now, pay when you stay

$113 nightly

$129 total

Jun 28 - Jun 29

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

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.

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 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 $503. 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.