Port Chester Vacations from $240

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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.
Outsite Chelsea

Outsite Chelsea

2 out of 5
Manhattan
Save 100% on your flight
Price was $428, price is now $240 per person
$240
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (26 reviews)
Was so clean! The only issue I had was waiting for the bathroom, but that’s to be expected at a place with shared bathrooms. Overall a good experience!

Reviewed on Nov 3, 2025

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Price was $571, price is now $242 per person
$242
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (2,030 reviews)
Nice room, great staff, The Wilson restaurant next store is super convenient. Would definitely recommend!

Reviewed on Nov 4, 2025

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was $574, price is now $296 per person
$296
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
Stayed in for one night and the room was beautiful. The bed was beyond comfortable and clean. From the check in to check out, staff was very helpful. 100% will recommend.

Reviewed on Oct 25, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was $1,573, price is now $878 per person
$878
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,012 reviews)
Nice hotel , needs a bit of tender love and care !

Reviewed on Oct 14, 2025

Night Hotel Broadway

Night Hotel Broadway

2.5 out of 5
Manhattan
Price was $1,240, price is now $704 per person
$704
per person
Dec 8 - Dec 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7/10 Good! (2,477 reviews)
Location was great but too much noise outside and I could not sleep well for that reason

Reviewed on Nov 2, 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

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
Helicopter landing in a field in New York

Introductory Helicopter Flight Lesson from Westchester

$670
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
$144 nightly
The price is $168 total per night from Nov 16 to Nov 17
$168 total
Nov 16 - Nov 17
Total with taxes and fees
9/10 Wonderful! (2,717 reviews)
The hotel lobby has such an open space on different levels for guest relaxing , reading or doing computer work. I was only there for an over night and wish I could've stayed longer. My room was lovely&clean. Airport shuttle is a wonderful amenity.

Reviewed on Nov 3, 2025

Four Points by Sheraton Flushing
The Parc Hotel

The Parc Hotel

2.5 out of 5
3916 College Point Blvd, Flushing, NY
Fully refundableReserve now, pay when you stay
$125 nightly
The price is $147 total per night from Nov 19 to Nov 20
$147 total
Nov 19 - Nov 20
Total with taxes and fees
7.8/10 Good! (1,767 reviews)
Room is very clean.The staff is helpful and nice.Only thing thing missing is they need better breakfast selection.

Reviewed on Nov 3, 2025

The Parc Hotel
Ly New York Hotel

Ly New York Hotel

2.5 out of 5
15-61 127th St, College Point, NY
Fully refundableReserve now, pay when you stay
$132 nightly
The price is $155 total per night from Nov 9 to Nov 10
$155 total
Nov 9 - Nov 10
Total with taxes and fees
8.8/10 Excellent! (1,806 reviews)
Front desk staff were friendly, room was immaculate. And in my room at least, I had a great view of Manhattan in the distance.

Reviewed on Nov 3, 2025

Ly New York Hotel
See all 1,699 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 $240 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.