Port Chester Vacations from ￥276,548
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Port Chester Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza New York Times Square
Manhattan
￥276,548
per person
Nov 8 - Nov 13
found 12 hours ago
Roundtrip flight included
Tokyo (HND) to New York (JFK)
9/10 Wonderful! (3,331 reviews)
Location location, close to the best attraction and restaurants. Rooms are small. The breakfast is good, although the amount of people having breakfast is a lot.
Reviewed on Sep 7, 2026
Hotel Riu Plaza Manhattan Times Square
Manhattan
￥346,893
per person
Oct 17 - Oct 23
found 1 day ago
Roundtrip flight included
Tokyo (HND) to New York (JFK)
9.2/10 Wonderful! (3,950 reviews)
Great hotel! I’ll definitely book here again and breakfast was amazing everyday and the staff was so nice!
Reviewed on Sep 8, 2026
LGA AIRPORT
Queens
￥1,181,788
per person
Oct 17 - Oct 23
found 1 day ago
Roundtrip flight included
Tokyo (HND) to New York (JFK)
10/10 Exceptional! (2 reviews)
The best airbnb Ive stayed at in New York with the best price for our family of 6. The place was so clean, amenities looked brand new. It had a homey feel to it, my kids didnt want to leave. We will definently be booking again in the future.
Reviewed on Dec 24, 2025
NobleDEN Hotel
Manhattan
￥375,405
per person
Oct 17 - Oct 23
found 1 day ago
Roundtrip flight included
Tokyo (HND) to New York (JFK)
9.8/10 Exceptional! (1,643 reviews)
We loved this hotel. The location, rooftop patio, kind staff, and spacious, clean room were all amazing. We really enjoyed our stay and would come back in a heartbeat.
Reviewed on Sep 7, 2026
Find the Best Port Chester Vacation Packages
Port Chester Hotel Deals
Radio Hotel
2420 Amsterdam Ave New York NY
Fully refundableReserve now, pay when you stay
￥30,636
￥39,952 total
Sep 27 - Sep 28
includes taxes & fees
8.6/10 Excellent! (2,462 reviews)
"Loved it, planning to staying there again in my next trip"
Reviewed on Sep 7, 2026
Tarrytown House Estate
49 E Sunnyside Lane Tarrytown NY
￥27,593
￥35,413 total
Sep 9 - Sep 10
includes taxes & fees
8.2/10 Very Good! (1,293 reviews)
"I thought the pool area was a lot bigger in the pictures than in person. The rooms were okay, nothing special and some of the hallway areas in the estate felt a bit run down/smelled funky and gave off a little bit of a scary vibe that felt haunted. I guess it might actually be since the property ..."
Reviewed on Sep 8, 2026
Hampton Inn White Plains/Tarrytown
200 West Main Street Elmsford NY
Fully refundableReserve now, pay when you stay
￥17,444
￥19,950 total
Sep 20 - Sep 21
includes taxes & fees
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.
Stay near popular Port Chester attractions
Capitol Theatre
7.4/10 (117 reviews)
This historic venue captivates with exceptional acoustics and intimate performances from renowned artists. Arrive early to enjoy the theater's vintage architecture and pre-show ambiance in the stylish lounge areas.
Capitol Theatre - Garcia’s
After visiting Capitol Theatre - Garcia’s, make a plan to see the other sights and activities in Port Chester. Experience the area's live music and entertainment venues.
Port Chester-Rye Brook Public Library
Enjoy an outing to Port Chester-Rye Brook Public Library during your stay in Port Chester. Amble around the area's waterfront or experience its live music.
Clay Art Center Gallery
This renowned ceramic arts hub showcases exhibitions from emerging and established artists since 1957. Explore the gallery, join a Wednesday morning tour, and find unique handcrafted pieces in their retail shop.
What to do in Port Chester
Sleepy Hollow Ghost Tour (Self-Guided Audio Driving/Walking Tour)
￥800
per adult
Spa-Quality On Demand Massage - Westchester County
￥29,457
per adult
Introductory Helicopter Flight Lesson from Westchester
￥112,863
per traveler
Frequently asked questions
How much does a Port Chester vacation package cost?
Offering excellent value package deals from ￥276,548 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?
The off-season is the best time to travel to Port Chester if you're trying to keep costs down. Another tip for finding cheap Port Chester vacation packages? Try to avoid public holidays and any major events.
How many days is enough for Port Chester?
The ideal duration of your Port Chester vacation depends on what you'd like to see and do. Usually, a few days to a week will give you plenty of time to visit all the major attractions and explore some hidden gems along the way.
Is it worth booking a vacation package to Port Chester?
It's easy to see why a Port Chester vacation is on the to-do list of many travelers. Top attractions like Capitol Theatre are just the start of what you can explore 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.
How to plan a trip to Port Chester?
- Choose when to travel: Check your calendar and get your bags packed. Your favorite season and the type of activities available will also help you decide when to escape to Port Chester.
- Budget wisely: In addition to the cost of your accommodations, you should consider other expenses too. These include food, transportation and flights. Also, set aside a little extra for unexpected expenses that could arise during your trip to Port Chester.
- Determine how many days away: Start by compiling a list of the attractions you want to get to in Port Chester. Then, estimate how long you'll need for each, along with any travel time.
- Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a personalized Port Chester vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
