Port Chester Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Flight + Hotel Deals in Port Chester
Price found within the past 48 hours. Click for updated prices.
OYO Times Square
Manhattan
€1,154
per person
19 Oct - 25 Oct
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
6.8/10 (2,037 reviews)
Amazing location for anyone wanting to see broadway shows! Right in times Square and just a few steps away from the TKTS discount booth!
Reviewed on 9 Aug 2026
Top hotels in Port Chester
Highbridge Hotel
1263 Edward L Grant Highway Bronx NY
Fully refundableReserve now, pay when you stay
€75
20 Aug - 21 Aug
includes taxes & fees
Four Points by Sheraton Flushing
33-68 Farrington St Flushing NY
Fully refundableReserve now, pay when you stay
€151
17 Aug - 18 Aug
includes taxes & fees
Sonesta White Plains Downtown
66 Hale Ave White Plains NY
Fully refundableReserve now, pay when you stay
€186
30 Aug - 31 Aug
includes taxes & fees
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.
Stay near popular Port Chester attractions
Capitol Theatre
7.4/10 (117 reviews)
This historic venue captivates with exceptional acoustics and intimate performances from renowned artists. Arrive early to enjoy the theater's vintage architecture and pre-show ambiance in the stylish lounge areas.
Clay Art Center Gallery
This renowned ceramic arts hub showcases exhibitions from emerging and established artists since 1957. Explore the gallery, join a Wednesday morning tour, and find unique handcrafted pieces in their retail shop.
Capitol Theatre - Garcia’s
After visiting Capitol Theatre - Garcia’s, make a plan to see the other sights and activities in Port Chester. Experience the area's live music and entertainment choices.
Port Chester-Rye Brook Public Library
Enjoy an outing to Port Chester-Rye Brook Public Library during your stay in Port Chester. Amble around the area's waterfront or experience its live music.
What to do in Port Chester
Introductory Helicopter Flight Lesson from Westchester
€1,136
per traveller
Frequently asked questions
How much does a Port Chester holiday package cost?
Offering excellent value package deals from €1,154 on Expedia, you'll be thrilled with how little a holiday 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?
The off-season is the best time to travel to Port Chester if you're trying to keep costs down. Another tip for finding cheap Port Chester holiday packages? Try to avoid public holidays and any major events.
How many days is enough for Port Chester?
The ideal duration of your Port Chester holiday depends on what you'd like to see and do. Usually, a few days to a week will give you plenty of time to visit all the major attractions and explore some hidden gems along the way.
Is it worth booking a holiday package to Port Chester?
It's easy to see why a Port Chester holiday is on the to-do list of many travellers. Top attractions like Capitol Theatre are just the start of what you can explore 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 personalise your search by "Amenities," "Property type," "Traveller 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 holiday as a package?
You can enjoy significant savings on your next Port Chester break by booking a personalised holiday package. Check the "Package" heading, then enter your travel dates and destination to view the best airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday 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.
How to plan a trip to Port Chester?
- Choose when to travel: Check your calendar and get your bags packed. Your favourite season and the type of activities available will also help you decide when to escape to Port Chester.
- Budget wisely: In addition to the cost of your accommodation, you should consider other expenses too. These include food, transportation and flights. Also, set aside a little extra for unexpected expenses that could arise during your trip to Port Chester.
- Determine how many days away: Start by compiling a list of the attractions you want to get to in Port Chester. Then, estimate how long you'll need for each, along with any travel time.
- Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a personalised Port Chester holiday package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
