Port Chester Vacations from $847
Book a Hotel + Flight or Car together to unlock savings
The Latest Port Chester Vacation Packages
- Hotel St. James
Oct 20 - Oct 25Hotel St. James + Flight
Manhattan5 nights3.0 star property8.8/10 - Excellent (7,748 reviews)"There was dust on the headboard, the sheets were wrinkled, and I found hair on the pillow. However, it is quiet and the staff is friendly. It could be more appealing if they made changes—like adding a coffee maker or small fridge to the room and making better use of the bar. It could be a very attractive hotel given its historic character, but it needs a little more TLC."Reviewed August 3, 2026Roundtrip • Atlanta (ATL) - New York (JFK)ATL - LGA • Nonstop EWR - ATL • Nonstop - Hotel Riu Plaza New York Times Square
Oct 20 - Oct 25Hotel Riu Plaza New York Times Square + Flight
Manhattan5 nights4.0 star property9.0/10 - Wonderful (3,271 reviews)Roundtrip • Atlanta (ATL) - New York (JFK)ATL - LGA • Nonstop EWR - ATL • Nonstop - Hotel Riu Plaza Manhattan Times Square
Oct 20 - Oct 25Hotel Riu Plaza Manhattan Times Square + Flight
Manhattan5 nights4.0 star property9.2/10 - Wonderful (3,836 reviews)"Great hotel! Felt extremely safe & secure traveling with my daughter. Staff was very helpful & friendly. Busy location right in the theater district. Room was quiet & clean. Would definitely stay again."Reviewed August 3, 2026Roundtrip • Atlanta (ATL) - New York (JFK)ATL - LGA • Nonstop EWR - ATL • Nonstop - The Wall Street Hotel
Oct 6 - Oct 11The Wall Street Hotel + Flight
Manhattan5 nights5.0 star property9.6/10 - Exceptional (734 reviews)"The hotel was extremely clean and well equipped. Beautiful design, friendly staff especially Eddie who is always ready:) The breakfast at the French Resto was amazing. The hotel also recognized our anniversary and celebrated with a bottle of champagne and a chocolate cake! Thanks Ivan. It’s all about the details and this place doesn’t disappoint."Reviewed August 2, 2026Roundtrip • Atlanta (ATL) - New York (JFK)ATL - LGA • Nonstop EWR - ATL • Nonstop$3,097$1,697found 1 day agoper traveler - NobleDEN Hotel
Oct 20 - Oct 25NobleDEN Hotel + Flight
Manhattan5 nights4.0 star property9.8/10 - Exceptional (1,634 reviews)"We loved the NobleDEN! Best location, walkable to everywhere, room had nice view over Grand Street. Would definitely stay again."Reviewed August 2, 2026Roundtrip • Atlanta (ATL) - New York (JFK)ATL - LGA • Nonstop EWR - ATL • Nonstop
Discover the most popular places to visit in Port Chester
Port Chester Hotel Deals
La Quinta Inn & Suites by Wyndham Stamford / New York City
La Quinta Inn & Suites by Wyndham Stamford / New York City
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
Holiday Inn Express & Suites Hawthorne Elmsford North by IHG
SpringHill Suites by Marriott Tuckahoe Westchester County
SpringHill Suites by Marriott Tuckahoe Westchester County
Baymont by Wyndham White Plains - Elmsford
Baymont by Wyndham White Plains - Elmsford
Frequently Asked Questions
How much does a Port Chester vacation package cost?
Offering excellent value package deals from $847 on Expedia, you'll be thrilled with how little a vacation to Port Chester costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Port Chester?
If you'd like to book a cheap Port Chester vacation package, consider planning a trip in February, September and October. You'll typically find better prices on hotels and flights during these months — perfect for travelers wishing to save money.
How many days is enough for Port Chester?
The ideal length of your Port Chester vacation depends on what you'd like to do. Generally, a few days to a week will give you enough time to go to all the major attractions and discover some hidden gems along the way.
Is it worth booking a vacation package to Port Chester?
It's no wonder a Port Chester vacation is on the must-do list of many travelers. Top attractions like Capitol Theatre are just the start of things to keep you busy here.
How to find the best Port Chester package deals?
Finding a cheap Port Chester package deal is a cinch with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, apply a few filters and see what's available. You can personalize your search by "Amenities," "Property type," "Traveler experience" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Port Chester package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Port Chester vacation as a package?
You can enjoy significant savings on your next Port Chester break by booking a personalized vacation package. Check the "Package" heading, then enter your travel dates and destination to view the best airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Port Chester?
Score incredible discounts by reserving your flights in advance with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for an impromptu Port Chester break.
Does Expedia offer Book Now, Pay Later Port Chester vacation packages?
Your Port Chester getaway is meant to be an escape from your daily routine, not a source of money worries. So to allow you a bit more flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.