Port Chester Vacations from $291

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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 $556, price is now $291 per person
$291
per person
May 7 - May 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
7.4/10 Good! (5,413 reviews)
Check in was horrible

Reviewed on Feb 19, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was $1,240, price is now $586 per person
$586
per person
May 7 - May 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,348 reviews)
Room is tiny and the walls are so thin! Heard kids next door yelling at 1:30 in the morning and the whole family started talking and yelling at 7 am. Will not book here again

Reviewed on Feb 19, 2026

Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
Price was $815, price is now $421 per person
$421
per person
May 7 - May 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (6,546 reviews)
Staff were friendly and the room served our needs. It was very basic, no coffee maker, fridge, etc. It did have a safe and hair dryer at least. It was clean and comfortable to come back after a night on the town. The oddest thing was no furniture in areas where some of the electrical outlets were. We ended up using our luggage as a makeshift table top.

Reviewed on Feb 19, 2026

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Price was $1,746, price is now $904 per person
$904
per person
Apr 22 - Apr 27
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.8/10 Exceptional! (1,411 reviews)
The room and hotel cleanliness, comfortable beds, friendly staff and convenient location

Reviewed on Feb 19, 2026

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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
$87 nightly
The price is $103 total per night from Feb 23 to Feb 24
$103 total
Feb 23 - Feb 24
Total with taxes and fees
8.6/10 Excellent! (2,023 reviews)
Room was nice and modern but parking was a nightmare.

Reviewed on Feb 17, 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
$124 nightly
The price is $142 total per night from Feb 22 to Feb 23
$142 total
Feb 22 - Feb 23
Total with taxes and fees
8.2/10 Very Good! (1,551 reviews)
Quiet location. Helpful Staff. I loved my housekeeper! She deserves a raise. I would stay again!

Reviewed on Feb 16, 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
$193 nightly
The price is $221 total per night from Mar 22 to Mar 23
$221 total
Mar 22 - Mar 23
Total with taxes and fees
8.6/10 Excellent! (1,288 reviews)
Front desk staff was above & beyond welcoming. The valet people were exceptionally helpful & sweet.

Reviewed on Feb 13, 2026

Sonesta White Plains Downtown
See all 1,799 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 $291 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.