Port Chester Vacations from $793
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 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
- Rest easyPlan, book, and manage your trip all in one place
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.
Seven Beach Lane
$793
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
9.4/10 Exceptional! (34 reviews)
Terrific first stay for our anniversary, and we will be back!
Jen and Kevin so sweet, helpful, and kind. Grounds are beautiful, rooms a bit small but pretty.
Watched Open in lobby late night, felt like we were home w a bigger TV.
Definite classy gem in Westhampton.
Reviewed on Sep 8, 2026
2 bedroom luxury Empire State VIEW
Manhattan
$1,286
per person
Dec 2 - Dec 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
6/10 (4 reviews)
One of the worst exp here, I have been charged for the trip, got my booking number, driving down to nyc, and was informed they are fully booked, having to wait 3hours to be on the phone to get a hotel room instead.
Reviewed on Aug 23, 2026
Hotel Riu Plaza New York Times Square
Manhattan
$1,293
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (3,331 reviews)
La espera de una habitación tardó más de lo normal eran las 4:45 y todavía seguimos esperando por la habitación 711 ya que teníamos 2 habitaciones una si fue entrega a las 3:20 y la otra de tardo más de 3 horas después, servicio muy bueno desayuno excelente personal excelente
Reviewed on Sep 9, 2026
OYO Times Square
Manhattan
$831
per person
Dec 2 - Dec 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
6.8/10 (2,082 reviews)
Not a clean room I asked for a wheelchair Accessible shower chair before I got to the hotel. It wasn’t provided for me at night. You could not get into the hotel. The revolving doors would not open and a person had to physically open the door from the inside to let people out from the outside in very small elevators, extremely noisy, extremely dirty rooms
Reviewed on Sep 9, 2026
Don't see what you're looking for?
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
Introductory Helicopter Flight Lesson from Westchester
$705
per traveler
Port Chester Hotel Deals
Radio Hotel
2420 Amsterdam Ave New York NY
Fully refundableReserve now, pay when you stay
$239 nightly
$278 total
Sep 27 - Sep 28
Total with taxes and fees
8.4/10 Very Good! (2,471 reviews)
"Amazing hotel, super fun area, rooms are very nice. The bathroom sink was a bit small, but that’s a very small nitpick."
Reviewed on Sep 10, 2026
Tarrytown House Estate
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
$181 nightly
$207 total
Sep 13 - Sep 14
Total with taxes and fees
Hampton Inn White Plains/Tarrytown
200 West Main Street Elmsford NY
Fully refundableReserve now, pay when you stay
$113 nightly
$129 total
Sep 27 - Sep 28
Total with taxes and 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.
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 |
More vacations you might like
Frequently asked questions
How much does a Port Chester vacation package cost?
Offering excellent value package deals from $793 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.
Explore a world of travel with Expedia
- Castle Gould
- New York Vacations
- Lehman Center for the Performing Arts
- Rye Playland
- New Roc City
- Statue of Liberty
- Palisades Vacations
- Brooklyn Bridge
- Fordham University
- Bethesda Fountain
- Chelsea Piers
- Saint Vladimir's Orthodox Theological Seminary
- Wall Street
- Everett Children's Adventure Garden
- Gantry Plaza State Park
- Manhasset Vacations
- Purchase Vacations
- Times Square
- Edward J. Murray Memorial Skating Center
- Great Neck Vacations
- Philipse Manor Hall State Historic Site
- Woodlawn Cemetery
- Bay Plaza Shopping Center
- Steppingstone Park
- Iona College
- Sands Point Preserve
- Manhattanville College
- College of New Rochelle
- Manhattan Vacations
- Bronx Vacations
- Thomas Paine Cottage Museum
- Rye Vacations
- Glen Island Park
- Tibbetts Brook Park
- New York Botanical Gardens
- Mount Vernon Vacations
- Sarah Lawrence College
- The Bronx Museum of the Arts
- Flushing Meadows-Corona Park
- Theater District Vacations
- Hudson Park and Beach
- Doral Arrowwood Golf Club
- New York Times Building
- Blum Center for Health
- Solomon R. Guggenheim Museum
- Harbor Links Golf Course
- Chrysler Building
- Newyork-Presbyterian - Westchester Hospital
- St. Patrick's Cathedral
- Science Barge
- Arthur Ashe Stadium
- Empire State Building
- Yonkers Raceway
- Yonkers Vacations
- Top of the Rock Observation Deck
- Lenoir Preserve
- Cudner-Hyatt House Complex
- Brooklyn Heights Promenade
- Roberto Clemente State Park
- Edgar Allan Poe Cottage
- American Museum of Natural History
- Kings Point Park
- Belvedere Castle
- 5th Avenue
- Columbus Circle
- Bowery Ballroom
- Hart Island
- Yankee Stadium
- Sleepy Hollow Vacations
- Sprain Lake Golf Course
- Westchester Hills Cemetery
- U.s. Merchant Marine Academy
- Tuckahoe Vacations
- Hudson River Museum
- Bronx Zoo
- Van Cortlandt Park
- Apollo Theater
- Scarsdale Vacations
- Hearst Tower
- Monroe College New Rochelle Campus
- Carnegie Hall
- Crooked Island Caves
- Nbc Studios
- Dobbs Ferry Vacations
- Metropolitan Museum of Art
- Ed Sullivan Theater
- Empire City Casino
- St. Paul's Church National Historic Site
- College of Mount Saint Vincent
- Port Washington Vacations
- Bartow Pell Mansion Museum
- Trump Tower
- Hastings-On-Hudson Vacations
- Pelham Bay Park
- New Rochelle Vacations
- Saddle Rock Grist Mill
- Capitol Theatre
- Orchard Beach
- Lincoln Center
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
