Port Chester Vacations

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Your Port Chester Vacation

When a city getaway is calling, answer it with a vacation package to Port Chester. The neighborhood of Downtown Stamford, which is good for history, bars and pubs and dining, makes a great base for your adventures. A trip to Port Chester is a wonderful opportunity to take in the sights. Check out well-known attractions like Capitol Theatre, Doral Arrowwood Golf Club and Clay Art Center Gallery. Stop daydreaming and start traveling. Browse the wide range of options on Expedia today and put your Port Chester vacation plans into gear!

Discover the most popular places to visit in Port Chester

Duran Duran plays the Capitol Theatre in Port Chester, NY in support of their Paper Gods album. Here they perform "Rio" to close out the night. #duranlive

Capitol Theatre

Enjoy a show at Capitol Theatre, a theater with a story to tell in Port Chester. Discover the entertainment choices and shops in this family-friendly area.

Capitol Theatre

Doral Arrowwood Golf Club

Enjoy a round of golf in Rye Brook at Doral Arrowwood Golf Club. Check out the shops and top-notch restaurants in this romantic area.

Doral Arrowwood Golf Club

Clay Art Center Gallery

Enjoy a stop at Clay Art Center Gallery, an entertaining place to visit in Port Chester. Amble around this family-friendly area's waterfront or experience its live music.

Clay Art Center Gallery

What to do in Port Chester

Self Guided Audio Ghost Tour of Sleepy Hollow

Self Guided Audio Ghost Tour of Sleepy Hollow

$10
per adult
Self Guided Audio Ghost Tour of Sleepy Hollow
Guided Kayak Fishing Tour

Guided Kayak Fishing Tour

$564
per adult
Guided Kayak Fishing Tour
Helicopter landing in a field in New York

Introductory Helicopter Flight Lesson from Westchester

$1,245
per traveler
Introductory Helicopter Flight Lesson from Westchester
See all activities in Port Chester

Port Chester Hotel Deals

Four Points by Sheraton Flushing

Four Points by Sheraton Flushing

3 out of 5
33-68 Farrington St Flushing NY
Fully refundableReserve now, pay when you stay
$140 nightly
The price is $164 total per night from Mar 22 to Mar 23
$164 total
Mar 22 - Mar 23
Total with taxes and fees
9/10 Wonderful! (2,950 reviews)
Clean pool. Nice staff. Room very clean. Onsite valet parking for 40 a night with in and out.

Reviewed on Mar 20, 2026

Four Points by Sheraton Flushing
Ly New York Hotel

Ly New York Hotel

2.5 out of 5
15-61 127th St College Point NY
Fully refundable
$103 nightly
The price is $122 total per night from Mar 22 to Mar 23
$122 total
Mar 22 - Mar 23
Total with taxes and fees
8.8/10 Excellent! (2,087 reviews)
The room was spacious and each guest had complimentary slippers! FYI-If the sink’s plug is closed, you have to press down and release it to open. (We had to call for help.)

Reviewed on Mar 19, 2026

Ly New York Hotel
Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

2.5 out of 5
540 Saw Mill River Rd Elmsford NY
Fully refundableReserve now, pay when you stay
$112 nightly
The price is $128 total per night from Mar 29 to Mar 30
$128 total
Mar 29 - Mar 30
Total with taxes and fees
8.2/10 Very Good! (1,609 reviews)
I was there for Match Day ceremony today at New York Medical College. It was a great place to stay for the event

Reviewed on Mar 20, 2026

Baymont by Wyndham White Plains - Elmsford
See all 1,787 properties in Port Chester
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.

Find the Best Port Chester Vacation Packages

Port Chester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
John F. Kennedy Intl. Airport (JFK)
Population
29,600
Top Sights
Capitol Theatre, Doral Arrowwood Golf Club and Clay Art Center Gallery

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Frequently asked questions

How much does a Port Chester vacation package cost?
Offering excellent value package deals 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.