Port Chester Vacations from $351

Book a Hotel + Flight or Car together to unlock savings

Photo by Shosh

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.
Somerset Hills Hotel, Tapestry Collection by Hilton

Somerset Hills Hotel, Tapestry Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $604, price is now $351 per person
$351
per person
Nov 15 - Nov 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
8.8/10 Excellent! (215 reviews)
Overall great location and friendly staff

Reviewed on Oct 6, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $3,246, price is now $1,676 per person
$1,676
per person
Nov 17 - Nov 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,006 reviews)
Every staff person I interacted with was friendly and helpful. Loved the views and location. Wished there was more room to walk in the living room when the pull out sofa was open.

Reviewed on Sep 28, 2025

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Save 100% on your flight
Price was $940, price is now $502 per person
$502
per person
Dec 14 - Dec 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,008 reviews)
The room and grounds were very good

Reviewed on Sep 30, 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,359, price is now $765 per person
$765
per person
Dec 14 - Dec 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.8/10 Exceptional! (1,344 reviews)
The most inconvenient location ever. Streets dirty around the hotel. The room was so tiny and awkwardly set up. That half your bathroom was next to the bed. The only thing in its own room was a toilet even the mirror hung next to the bed over the bathroom sink And housekeeping did a terrible job though the room was clean when we first walked in. I would never stay there again and I would never stay in that area.

Reviewed on Oct 6, 2025

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,128, price is now $654 per person
$654
per person
Dec 9 - Dec 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (2,730 reviews)
Great service since the moment our taxi drop us, and Ramon welcomed us. The check in was smooth and friendly. Although there was a little queue for breakfast, the dining room is huge and the breakfast more than complete. Great service everywhere. The hotel is conveniently located for time square and all shows in Broadway. I will definitely return to this hotel.

Reviewed on Oct 8, 2025

Don't see what you're looking for?
See all available trips from Columbus to Port Chester
View all trips

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

3.5/5(42 reviews)

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 family-friendly area.

Doral Arrowwood Golf Club

Blum Center for Health

Though Blum Center for Health might be what brings you to town, perhaps you'll have a chance to explore more of Rye Brook while you are here.

Blum Center for Health

What to do in Port Chester

LEGOLAND® Discovery Center Westchester Tickets

LEGOLAND® Discovery Center Westchester Tickets

$30
per adult
76% of travellers recommend
LEGOLAND® Discovery Center Westchester Tickets
Guided Kayak Fishing Tour

Guided Kayak Fishing Tour

$564
per adult
Guided Kayak Fishing Tour
See all activities in Port Chester

Port Chester Hotel Deals

Executive Inn - Fort Lee

Executive Inn - Fort Lee

3.5 out of 5
2339 Route 4, Fort Lee, NJ
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $112 total per night from Oct 12 to Oct 13
$112 total
Oct 12 - Oct 13
Total with taxes and fees
7.6/10 Good! (487 reviews)
"Easy access to the GWB"

Reviewed on Oct 5, 2025

Executive Inn - Fort Lee
The Parc Hotel

The Parc Hotel

2.5 out of 5
3916 College Point Blvd, Flushing, NY
Fully refundableReserve now, pay when you stay
$170 nightly
The price is $199 total per night from Oct 21 to Oct 22
$199 total
Oct 21 - Oct 22
Total with taxes and fees
7.8/10 Good! (1,691 reviews)
"Great room. Decent gym. Good proximity to airport."

Reviewed on Oct 2, 2025

The Parc Hotel
Armoni Inn & Suites

Armoni Inn & Suites

3.5 out of 5
329 Route 303, Orangeburg, NY
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $109 total per night from Oct 14 to Oct 15
$109 total
Oct 14 - Oct 15
Total with taxes and fees
6/10 (2,056 reviews)
"Clean, cozy, great location, very quiet."

Reviewed on Oct 3, 2025

Armoni Inn & Suites
See all 1,660 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.

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

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Port Chester vacation package cost?
Offering excellent value package deals from $351 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

Explore a world of travel with Expedia

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