Port Chester Vacations from $206

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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.
Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was $438, price is now $206 per person
$206
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7.4/10 Good! (5,413 reviews)
The elevators are kinda sketchy right now. Only a couple are working and they have been malfunctioning since we arrived.

Reviewed on Dec 21, 2025

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Price was $522, price is now $240 per person
$240
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (2,008 reviews)
Everyone was great and the room has a fabulous view.

Reviewed on Dec 21, 2025

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was $877, price is now $447 per person
$447
per person
Feb 27 - Mar 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
Always so accommodating to my needs when I come to stay

Reviewed on Dec 20, 2025

Hotel Seville Nomad, in the Unbound Collection by Hyatt

Hotel Seville Nomad, in the Unbound Collection by Hyatt

4.5 out of 5
Manhattan
Save 100% on your flight
Price was $1,055, price is now $542 per person
$542
per person
Mar 8 - Mar 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,184 reviews)
Clean room, staff were very helpful and kind.

Reviewed on Dec 20, 2025

Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Manhattan
Price was $1,323, price is now $710 per person
$710
per person
Mar 4 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (2,346 reviews)
Staff was amazing..,so kind, so helpful. From front desk to bistro to cleaners. Always smiling and willing to help you. Thanks for a wonderful stay!! We will be back !!

Reviewed on Dec 20, 2025

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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 family-friendly area.

Doral Arrowwood Golf Club

Clay Art Center Gallery

You can study the exhibits at Clay Art Center Gallery, a museum with a story of its own, during your travels to Port Chester. Take in the entertainment choices in this family-friendly area.

Clay Art Center Gallery

What to do in Port Chester

LEGOLAND® Discovery Center Westchester Tickets

LEGOLAND® Discovery Center Westchester Tickets

$30
per adult
88% 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

Radio Hotel

Radio Hotel

4 out of 5
2420 Amsterdam Ave New York NY
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $149 total per night from Jan 5 to Jan 6
$149 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
8.4/10 Very Good! (2,600 reviews)
The rooms were pretty spacious for what we needed! The front desk staff was awesome and they have vouchers for their little cafe and the bar next door!! Their cafe had the best little matcha. The only complaint I have is that the water temperate didn’t start or stay hot like in a normal hotel. Other ...

Reviewed on Dec 17, 2025

Radio Hotel
EVEN Hotel Norwalk by IHG

EVEN Hotel Norwalk by IHG

3.5 out of 5
426 Main Ave, Route 7 Norwalk CT
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $124 total per night from Jan 19 to Jan 20
$124 total
Jan 19 - Jan 20, 2026
Total with taxes and fees
8.2/10 Very Good! (1,023 reviews)
Great hidden gem

Reviewed on Dec 16, 2025

EVEN Hotel Norwalk by IHG
Four Points by Sheraton Flushing

Four Points by Sheraton Flushing

3 out of 5
33-68 Farrington St Flushing NY
$144 nightly
The price is $168 total per night from Jan 4 to Jan 5
$168 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9/10 Wonderful! (2,815 reviews)
The reception staff at Four Points by Sheraton, Flushing (Queens) were exceptionally helpful. I had misplaced my debit card upon arrival, and thanks to their incredible patience and support, I was able to contact my bank in England without any stress. Their professionalism and kindness truly stood ...

Reviewed on Dec 17, 2025

Four Points by Sheraton Flushing
See all 1,744 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 from $206 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.