Port Chester Vacations from $587
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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!
The Latest Port Chester vacation packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza New York Times Square
Manhattan
$836
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (3,334 reviews)
Great location, friendly and helpful staff. Breakfast and restaurant were lovely. Nothing negative to say, would stay again in a heartbeat.
Reviewed on Sep 6, 2026
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See all available trips from Columbus to Port Chester
View all tripsStay 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.
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 venues.
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.
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.
What to do in Port Chester
Sleepy Hollow Ghost Tour (Self-Guided Audio Driving/Walking Tour)
$5
per adult
Port Chester Hotel Deals
Radio Hotel
2420 Amsterdam Ave New York NY
Fully refundableReserve now, pay when you stay
$222 nightly
$258 total
Sep 27 - Sep 28
Total with taxes and fees
8.6/10 Excellent! (2,461 reviews)
"Great property! Always clean"
Reviewed on Sep 6, 2026
Tarrytown House Estate
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
$199 nightly
$228 total
Sep 8 - Sep 9
Total with taxes and fees
8.2/10 Very Good! (1,291 reviews)
"AC is older but everywhere clean."
Reviewed on Sep 7, 2026
Hampton Inn White Plains/Tarrytown
200 West Main Street Elmsford NY
Fully refundableReserve now, pay when you stay
$113 nightly
$129 total
Sep 20 - Sep 21
Total with taxes and fees
8/10 Very Good! (1,643 reviews)
"Location was ok but this wouldn't be somewhere I would stay again. Checked in went to turn the light on that wasn't working. Looking around and saw used condom in the trash. Had to call twice for someone to come change the garage."
Reviewed on Sep 7, 2026
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 from $587 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.
