Port Chester Vacations from $554

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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.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Save 100% on your flight
Price was $933, price is now $554 per person
$554
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
Rooms Property were Fantastic !

Reviewed on Feb 6, 2026

Topping Rose House

Topping Rose House

4.5 out of 5
Save 100% on your flight
Price was $1,320, price is now $679 per person
$679
per person
Mar 15 - Mar 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
9.2/10 Wonderful! (136 reviews)
Great rooms, staff and food

Reviewed on Sep 28, 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,628, price is now $977 per person
$977
per person
Apr 26 - May 1
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
9.8/10 Exceptional! (1,411 reviews)
NobleDEN has very clean rooms. The staff are also very friendly and accommodating. There are some nice amenities included in your stay including discounts at nearby establishments with your keycard! Cool and unexpected.

Reviewed on Feb 10, 2026

Hotel Beacon

Hotel Beacon

4 out of 5
Manhattan
Price was $1,220, price is now $748 per person
$748
per person
Apr 13 - Apr 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
9.4/10 Exceptional! (1,350 reviews)
Comfortable, friendly clean

Reviewed on Feb 9, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was $2,468, price is now $1,580 per person
$1,580
per person
Apr 30 - May 3
found 13 hours ago
Roundtrip flight included
San Juan (SJU) to New York (JFK)
8.8/10 Excellent! (1,000 reviews)
The entire stay was exceptional! From the point of entry to departure 10/10

Reviewed on Jan 29, 2026

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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

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

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

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
Self Guided Audio Ghost Tour of Sleepy Hollow

Self Guided Audio Ghost Tour of Sleepy Hollow

$10
per adult
Self Guided Audio Ghost Tour of Sleepy Hollow
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

Ly New York Hotel

Ly New York Hotel

2.5 out of 5
15-61 127th St College Point NY
Fully refundable
$88 nightly
The price is $104 total per night from Feb 17 to Feb 18
$104 total
Feb 17 - Feb 18
Total with taxes and fees
8.8/10 Excellent! (2,006 reviews)
This was my second stay and it was just as great as the first.

Reviewed on Feb 11, 2026

Ly New York Hotel
Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

2.5 out of 5
540 Saw Mill River Rd Elmsford NY
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $140 total per night from Feb 22 to Feb 23
$140 total
Feb 22 - Feb 23
Total with taxes and fees
8.2/10 Very Good! (1,541 reviews)
Room was clean Good location Would definitely stay again

Reviewed on Feb 11, 2026

Baymont by Wyndham White Plains - Elmsford
Sonesta White Plains Downtown

Sonesta White Plains Downtown

4 out of 5
66 Hale Ave White Plains NY
Fully refundableReserve now, pay when you stay
$187 nightly
The price is $214 total per night from Mar 5 to Mar 6
$214 total
Mar 5 - Mar 6
Total with taxes and fees
8.8/10 Excellent! (1,282 reviews)
Well located, clean, friendly staff.

Reviewed on Feb 11, 2026

Sonesta White Plains Downtown
See all 1,791 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 $554 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.