Port Chester Vacation Packages
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Top Port Chester vacation deals
- Radio Hotel
Sept 10 - Sept 13Radio Hotel + Flight
Manhattan3 nights4.0 star property8.6/10 - Excellent (2,495 reviews)"Execllent"Reviewed August 5, 2026Roundtrip • Toronto (YTO) - New York (JFK)YTZ - EWR • Nonstop EWR - YTZ • NonstopCA $1,387CA $866found 1 day agoper traveller - The Wall Street Hotel
Oct 9 - Oct 14The Wall Street Hotel + Flight
Manhattan5 nights5.0 star property9.6/10 - Exceptional (737 reviews)Roundtrip • Toronto (YTO) - New York (JFK)YYZ - EWR • Nonstop EWR - YYZ • NonstopCA $4,609CA $2,582found 1 day agoper traveller - The Kitano Hotel New York
Oct 9 - Oct 14The Kitano Hotel New York + Flight
Manhattan5 nights4.5 star property9.4/10 - Exceptional (2,318 reviews)"Staff was very friendly and welcoming. Amazing rooftop bar and a must stop. Conveniently located a few blocks from Grand Central station. We will likely visit and book hotel again as a family."Reviewed August 4, 2026Roundtrip • Toronto (YTO) - New York (JFK)YYZ - EWR • Nonstop EWR - YYZ • NonstopCA $2,903CA $1,818found 1 day agoper traveller - Hotel Riu Plaza Manhattan Times Square
Oct 10 - Oct 14Hotel Riu Plaza Manhattan Times Square + Flight
Manhattan4 nights4.0 star property9.2/10 - Wonderful (3,849 reviews)Roundtrip • Hamilton (YHM) - New York (JFK)YTZ - LGA • Nonstop EWR - YYZ • NonstopCA $2,705CA $1,707found 1 day agoper traveller - Hotel Riu Plaza New York Times Square
Oct 10 - Oct 14Hotel Riu Plaza New York Times Square + Flight
Manhattan4 nights4.0 star property9.0/10 - Wonderful (3,269 reviews)"The only issue with the room...of the bathroom light was on, you could see the person in the shower...the full silhouette at least. Breakfast was great as it was included with our rate. The cost was a tad higher than I wanted to pay at over $500 for 1 night, but the experience and location were wonderful."Reviewed August 5, 2026Roundtrip • Hamilton (YHM) - New York (JFK)YTZ - LGA • Nonstop EWR - YYZ • NonstopCA $2,833CA $1,795found 1 day agoper traveller
Discover the most popular places to visit in Port Chester
Port Chester Hotel Deals
"Very clean , great place"
"Room was clean. Convenient location for first stop after a long haul flight into JFK. Good parking."
Hampton Inn & Suites Yonkers - Westchester
Hampton Inn & Suites Yonkers - Westchester
"Staff was very friendly & efficient. The hotel was clean and nice/newish decor. Two drawbacks: The AC unit made a lot of noise turning off and on. Sounded like the door was being opened and closed. The other thing was there was not much soundproofing between the bedrooms. I could hear the guy sneeze in the next room and it wasn’t that obnoxious kind of loud sneeze. Could hear people out in the hallway quite easily."
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
Hampton Inn White Plains/Tarrytown
Hampton Inn White Plains/Tarrytown
Baymont by Wyndham White Plains - Elmsford
Baymont by Wyndham White Plains - Elmsford
Days Inn by Wyndham Elmsford / White Plains
Days Inn by Wyndham Elmsford / White PlainsFrequently Asked Questions
How much does a Port Chester vacation package cost?
Offering great value package deals from CA $866 on Expedia, you'll be thrilled with how little a vacation to Port Chester costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Port Chester?
Plan your trip for the off-peak season and you're likely to score cheap Port Chester vacation packages. Bear in mind that public holidays and local events and festivals can have an impact on prices, so do your research before booking.
How many days is enough for Port Chester?
To fully enjoy your Port Chester vacation, we suggest booking for 2 days. Split your time between discovering Greenwich Point Park, Doral Arrowwood Golf Club and other major sights, in addition to experiencing neighbourhoods like Greenwich Municipal Centre Historic District and Strickland Road Historic District. If you've got some time to spare, include a day trip or tour in your Port Chester vacation itinerary.
Is it worth booking a vacation package to Port Chester?
Port Chester has everything you need for an amazing escape. Get your Port Chester vacation off to a flying start by exploring major attractions like Capitol Theatre.
How to find the best Port Chester package deals?
Start your search for a Port Chester package deal by entering your travel dates and destination under our "Packages" tab. Then select some filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Port Chester package deal right away, just switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Port Chester adventure off to a flying start.
Is it cheaper to book a Port Chester vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking stays and flights individually. Better still, you can tailor your Port Chester escape to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Port Chester?
If you're planning a spontaneous Port Chester trip, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find amazing deals on your hotels and flights by booking well in advance.
How to plan a trip to Port Chester?
- Choose when to get away: Check your diary and get your bags packed. Your favourite time of year and the available activities will also help you decide when to vacation in Port Chester.
- Calculate your budget: Ensure you have enough money to cover everything from transportation and food to experiences and flights. Your accommodations will probably be the biggest expense during your trip to Port Chester.
- Decide your trip length: Think about how much time you want to spend exploring Port Chester. Plan your days so you can get to all the experiences and attractions you're interested in at a comfortable pace.
- Bundle your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to find a Port Chester vacation package that brings all your bookings together.