Ossining Vacation Packages 2026 from $833

Ossining flight + hotel vacation packages

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

Radio Hotel

Manhattan

Save 100% on your flight

$833

per person

Aug 26 - Sep 2

found 1 day ago

Roundtrip flight included

Dallas (DFW) to New York (JFK)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the express check-out and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.

2 bedroom luxury Empire State VIEW

Manhattan

$1,814

per person

Jul 27 - Jul 30

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Newark Liberty Intl. Airport (EWR)

Topping Rose House

$3,689

per person

Aug 9 - Aug 13

found 21 hours ago

Roundtrip flight included

Dallas (DFW) to New York (JFK)

A full-service spa, an outdoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and free valet parking. Enjoy the gym and perks like free self parking and a free area shuttle.

1 Hotel Brooklyn Bridge

Save 100% on your flight

$1,883

per person

Sep 18 - Sep 21

found 1 day 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.

Hotel Riu Plaza Manhattan Times Square

Manhattan

Save 100% on your flight

$919

per person

Sep 12 - Sep 15

found 1 day ago

Roundtrip flight included

Dallas (DAL) 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.

Top Ossining hotels deals

Windrose On Hudson

1 Shady Lane Farm Road Ossining NY

Free Cancellation

Reserve now, pay when you stay

$206 nightly

$230 total

Jun 28 - Jun 29

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

Armoni Inn & Suites

329 Route 303 Orangeburg NY

Free Cancellation

Reserve now, pay when you stay

$71 nightly

$79 total

Jun 30 - Jul 1

Total with taxes and fees

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

Baymont by Wyndham White Plains - Elmsford

540 Saw Mill River Rd Elmsford NY

Free Cancellation

Reserve now, pay when you stay

$131 nightly

$150 total

Jul 12 - Jul 13

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

Hyatt Regency Greenwich

1800 E Putnam Avenue Old Greenwich CT

Free Cancellation

Reserve now, pay when you stay

$184 nightly

$212 total

Jul 26 - Jul 27

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.

Pool

Pet friendly

Sonesta White Plains Downtown

66 Hale Ave White Plains NY

Free Cancellation

Reserve now, pay when you stay

$203 nightly

$232 total

Jul 26 - Jul 27

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

Tarrytown House Estate

49 E Sunnyside Lane Tarrytown NY

Free Cancellation

Reserve now, pay when you stay

$163 nightly

$186 total

Jun 30 - Jul 1

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.

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

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 $833. 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.