Port Chester Vacations from $758

Port Chester is a central urban destination known for family-friendly attractions, offering a blend of cultural experiences and nearby coastal relaxation. It provides a mix of entertainment options, such as the historic Capitol Theatre and the Clay Art Center Gallery, which is about a 5-minute walk from central Port Chester.


For those seeking outdoor fun, Rye Playland is about 1 mile away, and several beaches like Rye Beach and Oakland Beach are within about 2 miles. A Port Chester vacation package can easily combine urban exploration with nearby coastal relaxation and family entertainment.

When you bundle, you can save up to 30%*. To save money on a Port Chester package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

A Port Chester vacation offers a blend of entertainment, arts, and outdoor activities:


Browse and book things to do in Port Chester on Expedia.

Public transportation is a viable option for getting around during your Port Chester vacation package, especially for reaching nearby cities. The Metro-North Railroad's Port Chester station provides commuter rail service to Grand Central Terminal in New York City, as well as Stamford and New Haven in Connecticut. Local bus services, including the Bee-Line Bus System and Connecticut Transit Stamford Division, also operate within the area. For more flexibility or to reach destinations not covered by public transit, local taxis and ride-share apps are readily available.


For travelers booking Port Chester vacation packages with flights, public transit can connect you to major hubs, while a car or taxi offers convenience for exploring the immediate Port Chester area and its attractions.

A Port Chester vacation package can include hotels that offer convenient access to local restaurants and shops. While central Port Chester itself features walkable areas with attractions like the Clay Art Center Gallery about a 5-minute walk away, hotels like Courtyard by Marriott Rye are about 1 mile from the Capitol Theatre, an area often surrounded by dining and retail options. For a more upscale stay, the 4-star Delamar Greenwich Harbor, rated 9.5 out of 10, is about 3 miles from the Capitol Theatre, offering a short drive to the area's amenities.


Actual walking routes may differ from straight-line distances, so check the map for your selected hotel.

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Port Chester vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

To find last-minute vacation packages to Port Chester, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

Free cancellation on a Port Chester vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Port Chester getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.