Ossining Vacations
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Ossining Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
OYO Times Square
Manhattan
$831
per person
Oct 8 - Oct 12
found 22 hours ago
Roundtrip flight included
Nashville (BNA) to New York (JFK)
Stay at this hotel in New York. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Broadway and Times Square are located nearby.
The lobby is lovely, and of course we love Serendipity! For my stay, the Luggage Guy was THE BEST! We were so grateful for the 2;h bag check, as we arrived in NYC at 6am and couldn’t check in until 3pm. The front desk lines were frequently long and slow-moving, and when we were checking in around 4pm they told us there was no hot water, so they’d remove the facility fee if we wanted to stay, though when we went upstairs to our room the hot water was working fine and we didn’t have any trouble with it after 3 showers. I let the front desk know around 8pm that our water worked fine, and they were shocked. So like… whoever is in charge over here is not doing a very good job. I kept coming downstairs to check if the only ice machine was working yet - it said “refilling ice” every time I checked until I gave up at 11pm. It still wasn’t working when we checked out the next day either, and no one at the front desk had any idea how long it would take or how to fix it or even where to buy ice in the area. Our room wouldn’t get cold, so we called down and they said they’d send “the engineer” up but they never showed up. Also the carpet was wet near the bathroom and seemed soapy, but WAY too wet to be from any normal cleaning. The rooms were very quiet though! I didn’t hear anything from adjacent rooms - it seemed like no one was in there, so either that’s true or this hotel actually has decent walls. TBD. We did hear a lot of street noise from Times Square through the windows, which ev
Reviewed on Aug 31, 2026
Hotel Riu Plaza Manhattan Times Square
Manhattan
$1,381
per person
Oct 8 - Oct 12
found 22 hours ago
Roundtrip flight included
Nashville (BNA) to New York (JFK)
Stay at this hotel in New York. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Broadway and Rockefeller Center are located nearby.
The beds are comfortable. Great location, Times Square is just downstairs. There's a $99 property fee which didn't show when I book in Expedia.
Reviewed on Aug 31, 2026
The Ridge Hotel
Manhattan
$947
per person
Oct 8 - Oct 12
found 22 hours ago
Roundtrip flight included
Nashville (BNA) to New York (JFK)
Stay at this hotel in New York. Enjoy free WiFi, a rooftop terrace, and a business center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Brooklyn Bridge and Wall Street are located nearby.
Millennium Hotel Broadway Times Square
Manhattan
$993
per person
Oct 8 - Oct 12
found 22 hours ago
Roundtrip flight included
Nashville (BNA) to New York (JFK)
Book a stay at this business-friendly hotel in New York. Enjoy free WiFi, a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Times Square and Broadway are located nearby.
I paid for a double queen size bed room. The initial room I was given someone was already assigned the room. They gave me a second room with only one bed and told me they were totally booked for rooms with double beds (that I paid for months in advance) The third room was a King size bed and sofa and the bathroom wall was full of mold. After speaking with a manager who assured me that he would have the housekeeping manager take a look (he lied) I went into the lobby a fourth time and spoke with a different manager threatening to contact corporate then mysteriously a room was available with two beds. Inside of the fourth room was no working television but at that point myself and my roommate was totally over it. I will never book that hotel again. It’s filthy and the first manager was no help at all.
Reviewed on Aug 31, 2026
Ink 48 Hotel
Manhattan
$990
per person
Oct 8 - Oct 12
found 22 hours ago
Roundtrip flight included
Nashville (BNA) to New York (JFK)
Book a stay at this luxury hotel in New York. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Manhattan Cruise Terminal and Broadway are located nearby.
The Gotham Hotel
Manhattan
$1,104
per person
Oct 8 - Oct 12
found 22 hours ago
Roundtrip flight included
Nashville (BNA) to New York (JFK)
Book a stay at this luxury hotel in New York. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grand Central Terminal and Rockefeller Center are located nearby.
Very large and clean room. Very comfortable !
Reviewed on Aug 31, 2026
Ossining Vacation Packages
Trying to plan a way to package your Ossining flight and hotel, while saving some money? The AARP Travel Center Powered by Expedia® can help you get everything you need, while saving you both money and some time. We're here to book everything you'll need to make your Ossining trip one to remember. In only a few clicks, you can select the best Ossining vacation package for you. AARP Travel Center has a fabulous list of flights and hotels, as well as Ossining activities to pull from.
Ossining Hotel Deals
With 1282 hotels and resorts in Ossining to choose from, you will find one that is perfect for you.
We have competitive rates on everything from all-inclusive resorts that satisfy all the vacation must-haves to inexpensive accommodations perfect for those on looking to save. You can browse all the options and select the hotel that is ideal for you and your family. With AARP Travel Center's Ossining hotel packages, you not only get a great rate on your flight, but also a great place to stay.
Things to do in Ossining
People from all over make this city their vacation destination, and with good reason. A little curiosity and asking the right people, like your hotel's concierge, goes a long way into having a unique experience.
The AARP Travel Center "Things to Do" page has more great activities that you can book.
Package Your Ossining Vacation and Save
As an AARP Member, you can take advantage of all the great savings. You can save on select hotels worldwide, flights, and rental cars. No matter what vacation package you pick, you can rest easy knowing that you already saved on your trip. So what are you waiting for? Book today and get ready for your Ossining vacation.
Top Hotel Deals
Windrose On Hudson
1 Shady Lane Farm Road Ossining NY
Book a stay at this business-friendly hotel in Ossining. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Van Cortlandt Manor and ...
Tarrytown House Estate
49 E Sunnyside Lane Tarrytown NY
Book a stay at this business-friendly hotel in Tarrytown. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the restaurant and the helpful ...
Royal Regency Hotel
165 Tuckahoe Rd Yonkers NY
Book a stay at this business-friendly hotel in Yonkers. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant ...
Hampton Inn White Plains/Tarrytown
200 West Main Street Elmsford NY
Book a stay at this business-friendly hotel in Elmsford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Hyatt Regency Greenwich
1800 E Putnam Avenue Old Greenwich CT
Book a stay at this business-friendly hotel in Old Greenwich. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff ...
Armoni Inn & Suites
329 Route 303 Orangeburg NY
Book a stay at this business-friendly hotel in Orangeburg. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the clean rooms in our reviews. ...
Ramada by Wyndham Bronx
1000 Baychester Ave Bronx NY
Book a stay at this business-friendly hotel in Bronx. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Sleepy Hollow Hotel, a Dolce by Wyndham
455 S Broadway Tarrytown NY
Book a stay at this spa hotel in Tarrytown. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms ...
La Quinta Inn & Suites by Wyndham Stamford / New York City
135 Harvard Avenue Stamford CT
Stay at this hotel in Stamford. Enjoy free breakfast, free WiFi, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
Royal Hotel Bronx
3362 Boston Road Bronx NY
Stay at this hotel in Bronx. Enjoy free WiFi, a 24-hour front desk, and cable TV channels. Popular attractions Yankee Stadium and Bronx Zoo are located ...
West Gate Inn Nyack
26 Route 59 Nyack NY
Book a stay at this business-friendly hotel in Nyack. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Ethan Allen Hotel
21 Lake Avenue Extension Danbury CT
Book a stay at this business-friendly hotel in Danbury. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
Amsterdam Hotel
19 Clarks Hill Ave Stamford CT
Book a stay at this business-friendly hotel in Stamford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
LIV Hotel Bronx - Newly Built
3530 Webster Ave Bronx NY
Stay at this hotel in Bronx. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Yankee Stadium and Bronx Zoo are located nearby.
Crowne Plaza Suffern - Mahwah by IHG
3 Executive Blvd Suffern NY
Book a stay at this business-friendly hotel in Suffern. Enjoy free WiFi, free parking, and 2 bars/lounges. Our guests praise the breakfast and the helpful staff ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Wed, Nov 18 - Sun, Nov 22
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$132
Roundtrip
found 2 days ago
Sat, Oct 31 - Fri, Nov 6
DFW
Dallas-Fort Worth Intl.
LGA
LaGuardia
$177
Roundtrip
found 4 days ago
Sat, Oct 24 - Mon, Nov 9
MCO
Orlando Intl.
LGA
LaGuardia
$207
Roundtrip
found 6 days ago
Tue, Oct 6 - Sat, Oct 10
FLL
Fort Lauderdale - Hollywood Intl.
LGA
LaGuardia
$209
Roundtrip
found 1 day ago
Tue, Oct 6 - Sat, Oct 10
FLL
Fort Lauderdale - Hollywood Intl.
LGA
LaGuardia
$209
Roundtrip
found 1 day ago
Best points of interest in Ossining
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- Louis Engel Waterfront Park Vacations
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