Port Chester Vacations from $930
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The Latest Port Chester Vacation Packages
- Radio Hotel
Sep 21 - Sep 26Radio Hotel + Flight
Manhattan5 nights4.0 star property8.6/10 - Excellent (2,492 reviews)Roundtrip • Atlanta (ATL) - New York (JFK)ATL - JFK • Nonstop JFK - ATL • Nonstop - The Wall Street Hotel
Sep 24 - Sep 27The Wall Street Hotel + Flight
Manhattan3 nights5.0 star property9.6/10 - Exceptional (733 reviews)"Excellent Staff, clean rooms, etc.. in room dining. However roof terrace is only for exclusive events"Reviewed August 2, 2026Roundtrip • Atlanta (ATL) - New York (JFK)ATL - LGA • Nonstop EWR - ATL • Nonstop$2,083$1,142found 2 days agoper traveler - Sound View Greenport
Sep 21 - Sep 26Sound View Greenport + Flight
Greenport5 nights4.0 star property8.4/10 - Very Good (674 reviews)"The location itself is great. The customer service is awful"Reviewed August 1, 2026Roundtrip • Atlanta (ATL) - New York (JFK)ATL - JFK • Nonstop JFK - ATL • Nonstop - Pestana Park Avenue
Oct 17 - Oct 22Pestana Park Avenue + Flight
Manhattan5 nights4.0 star property9.2/10 - Wonderful (890 reviews)"Clean room and very pleasant"Reviewed August 2, 2026Roundtrip • Dallas (DFW) - New York (JFK)DFW - LGA • Nonstop LGA - DFW • Nonstop - Hotel Riu Plaza Manhattan Times Square
Sep 24 - Sep 27Hotel Riu Plaza Manhattan Times Square + Flight
Manhattan3 nights4.0 star property9.2/10 - Wonderful (3,833 reviews)"The rooms are very small definitely not meant to share place with another person. There's no microwave or ice bucket available in the room."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 $930 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.