Deals on vacations and trips to Ossining

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Ossining flight + hotel vacation packages

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Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $961, price is now $587 per person
$587
per person
Nov 20 - Nov 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
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.
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $4,269, price is now $2,299 per person
$2,299
per person
Nov 12 - Nov 17
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.
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,503, price is now $836 per person
$836
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
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 High Line Hotel

The High Line Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was $2,202, price is now $1,333 per person
$1,333
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
This hotel features a bar/lounge, a coffee shop, and free WiFi in public areas. A terrace, a garden, and dry cleaning are also on offer.
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Manhattan
Save 100% on your flight
Price was $1,099, price is now $690 per person
$690
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
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.

Top Ossining hotels deals

Windrose On Hudson

Windrose On Hudson

3 out of 5
1 Shady Lane Farm Road Ossining NY
Free Cancellation
Reserve now, pay when you stay
$224 nightly
The price is $250 total per night
$250 total
Sep 27 - Sep 28
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
Tarrytown House Estate

Tarrytown House Estate

3.5 out of 5
49 E Sunnyside Lane Tarrytown NY
Free Cancellation
Reserve now, pay when you stay
$201 nightly
The price is $230 total per night
$230 total
Sep 8 - Sep 9
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
Royal Regency Hotel

Royal Regency Hotel

3.5 out of 5
165 Tuckahoe Rd Yonkers NY
Free Cancellation
Reserve now, pay when you stay
$118 nightly
The price is $139 total per night
$139 total
Sep 27 - Sep 28
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
Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

3 out of 5
200 West Main Street Elmsford NY
Free Cancellation
Reserve now, pay when you stay
$113 nightly
The price is $129 total per night
$129 total
Sep 13 - Sep 14
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.
Breakfast included
Pet friendly
Hyatt Regency Greenwich

Hyatt Regency Greenwich

4 out of 5
1800 E Putnam Avenue Old Greenwich CT
Free Cancellation
Reserve now, pay when you stay
$182 nightly
The price is $209 total per night
$209 total
Sep 27 - Sep 28
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

Sonesta White Plains Downtown

4 out of 5
66 Hale Ave White Plains NY
Free Cancellation
Reserve now, pay when you stay
$212 nightly
The price is $242 total per night
$242 total
Sep 27 - Sep 28
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, laundry service, and valet parking. Enjoy the 24-hour gym and perks like free airport pick-up.
Pool
Free airport shuttle
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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.

Stay near popular Ossining attractions

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.
See properties

Frequently asked questions

How much are vacation packages to Ossining?
You can pick up an excellent hotel and flight bundle for as low as $587. 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.

Photos of local treasures

Browse Ossining vacation photos for more inspiration

A wooden boardwalk winding through a forest with autumn foliage.
A lake surrounded by autumn-colored trees and houses on a hillside.
A wooden bridge over a lake with a sign reading "BERGMANN BOARDWALK".
A row of historic buildings with distinct architectural styles, including a red brick building with a clock tower and a white building with ornate detailing.
A sunset over a calm lake with several boats anchored.