Port Chester Vacations from $400

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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.
San Carlos Hotel

San Carlos Hotel

4.5 out of 5
Manhattan
Save 100% on your flight
Price was $717, price is now $400 per person
$400
per person
Feb 4 - Feb 8
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (NYC)
9.4/10 Exceptional! (1,685 reviews)
Perfect location, hospitality, cleanliness, comfortable bedrooms!!!

Reviewed on Dec 3, 2025

Luxury Living in the Heart of NY

Luxury Living in the Heart of NY

4 out of 5
Southeast Yonkers
Price was $1,075, price is now $522 per person
$522
per person
Feb 13 - Feb 18
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (QLA) to White Plains (HPN)
2/10 (1 review)
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Save 100% on your flight
Price was $1,197, price is now $585 per person
$585
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to New York (NYC)
9.2/10 Wonderful! (2,008 reviews)
No issues. Nice property, good location, attentive staff. Only knock is that the family suite has some very sharp edges that are eye-level for kids and had us worried. Throw some corner protectors on those and it’s a very reasonably sized and comfortable launching point for exploring Manhattan.

Reviewed on Dec 3, 2025

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Save 100% on your flight
Price was $791, price is now $447 per person
$447
per person
Jan 10 - Jan 14
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (NYC)
9.2/10 Wonderful! (1,002 reviews)
I stay here often and the rooms are spacious clean and the hotel staff is very accommodating. I always have a wonderful experience and I highly recommend staying here. They also offer free breakfast and dinner which is a nice perk.

Reviewed on Nov 25, 2025

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,097, price is now $627 per person
$627
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to New York (NYC)
9.2/10 Wonderful! (3,348 reviews)
Only thing our room had hair all over floor

Reviewed on Dec 4, 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
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

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
$149 nightly
The price is $174 total per night from Jan 4 to Jan 5
$174 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9/10 Wonderful! (2,766 reviews)
Nice

Reviewed on Nov 29, 2025

Four Points by Sheraton Flushing
Radio Hotel

Radio Hotel

4 out of 5
2420 Amsterdam Ave New York NY
Fully refundableReserve now, pay when you stay
$147 nightly
The price is $172 total per night from Jan 4 to Jan 5
$172 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.4/10 Very Good! (2,638 reviews)
We loved it and the restaurant but for Friday night. We were on the 10th floor and the he music from the Event space on the 12th floor shock and pounded us till 4 am. If you like to sleep at night come here weeknights ONLY!

Reviewed on Nov 29, 2025

Radio Hotel
The Parc Hotel

The Parc Hotel

2.5 out of 5
3916 College Point Blvd Flushing NY
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $103 total per night from Jan 4 to Jan 5
$103 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
7.8/10 Good! (1,822 reviews)
The place was clean.

Reviewed on Nov 29, 2025

The Parc Hotel
See all 1,706 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 $400 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.