Port Chester Vacations from $377

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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.
Windrose On Hudson

Windrose On Hudson

2 out of 5
Save 100% on your flight
per person
Aug 16 - Aug 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
No reviews
I regret I didn’t take pictures, but the scenery was beautiful

Reviewed on Jun 24, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,004 reviews)
We liked everything. Thank you so much!

Reviewed on Jul 7, 2025

Hotel 27 by LuxUrban

Hotel 27 by LuxUrban

2.5 out of 5
Manhattan
per person
Sep 14 - Sep 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7.6/10 Good! (803 reviews)
Best experience ever!! Fabulous staff and cleanliness

Reviewed on Jul 5, 2025

Empire Hotel

Empire Hotel

4 out of 5
Manhattan
Save 100% on your flight
per person
Sep 14 - Sep 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7.6/10 Good! (5,584 reviews)
Our family greatly enjoyed the convenience of Empire Hotel. The highlights were: 1) excellent location (scenic, near Central Park and lots of restaurants, convenient access to coffee & shops, etc.), 2) rooftop pool gave our kids a great afternoon option on a super hot lazy day, 3) the staff was kind and responsive. Noting that our room phone did not connect to the front desk (always a busy signal when I pressed the front desk button), but I just called the hotel number from my cell phone and got thru there. Overall I would highly recommend!

Reviewed on Jul 8, 2025

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (3,385 reviews)
Good location. Nice size rooms.

Reviewed on Jul 9, 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 romantic 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
Couple's Private New York Helicopter Tour from Westchester

Couple's Private NYC Helicopter Tour from Westchester

$950
per traveler
Couple's Private NYC Helicopter Tour from Westchester
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

EVEN Hotel Norwalk by IHG
EVEN Hotel Norwalk by IHG
3.5 out of 5
426 Main Ave, Route 7, Norwalk, CT
Fully refundable
$108 nightly
The price is $124 total per night from Aug 4 to Aug 5
$124 total
Aug 4 - Aug 5
Total includes taxes and fees
8.2/10 Very Good! (1,003 reviews)
"A very quiet space, very kind staff."

Reviewed on Jul 8, 2025

EVEN Hotel Norwalk by IHG
Radio Hotel
Radio Hotel
4 out of 5
2420 Amsterdam Ave, New York, NY
Fully refundableReserve now, pay when you stay
$163 nightly
The price is $191 total per night from Jul 13 to Jul 14
$191 total
Jul 13 - Jul 14
Total includes taxes and fees
8.6/10 Excellent! (2,576 reviews)
"Property was perfectly fine. It was rather small but that's what you expect I suppose in Manhattan. It was a weird thing where we had to buy two drinks for $22 to get the hotel room. I would have preferred not to have had the drink. The bed was comfortable everything was adequate. We were close to ..."

Reviewed on Jul 4, 2025

Radio 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
$117 nightly
The price is $138 total per night from Jul 15 to Jul 16
$138 total
Jul 15 - Jul 16
Total includes taxes and fees
8.8/10 Excellent! (1,450 reviews)
"Really comfortable beds. Fast & friendly check-in."

Reviewed on Jul 8, 2025

Ly New York Hotel
See all 1,603 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 $377 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.