Port Chester Vacation Packages
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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!
Top Port Chester Vacation Deals
Price found within the past 48 hours. Click for updated prices.
1 Hotel Brooklyn Bridge
CA $1,777
per person
Nov 9 - Nov 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,013 reviews)
We flew in to attend the U.S. Open and stayed at 1 Hotel Brooklyn. The staff was warm, welcoming, and attentive throughout our stay. The views of Manhattan and the Brooklyn Bridge are truly hard to beat. We had a wonderful experience and would absolutely stay here again!
Reviewed on Sep 5, 2026
OYO Times Square
Manhattan
CA $1,104
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
6.8/10 (2,083 reviews)
Great place to crash if yiu dont care about amenities. Clean room but needs updated and painted and repaired. Bed was firm.
Reviewed on Sep 5, 2026
Ready to book your vacation to Port Chester?
Port Chester Hotel Deals
Radio Hotel
2420 Amsterdam Ave New York NY
Fully refundableReserve now, pay when you stay
CA $189
CA $260 total
Sep 7 - Sep 8
includes taxes & fees
Tarrytown House Estate
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
CA $248
CA $318 total
Sep 7 - Sep 8
includes taxes & fees
Hampton Inn White Plains/Tarrytown
200 West Main Street Elmsford NY
Fully refundableReserve now, pay when you stay
CA $157
CA $179 total
Sep 13 - Sep 14
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)
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 - 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
Enjoy a stop at Clay Art Center Gallery, an entertaining place to visit in Port Chester. Amble around this family-friendly area's waterfront or experience its live music.
What to do in Port Chester
Introductory Helicopter Flight Lesson from Westchester
CA $975
per traveller
Frequently asked questions
How much does a Port Chester vacation package cost?
Offering great value package deals from CA $1,090 on Expedia, you'll be thrilled with how little a vacation to Port Chester costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Port Chester?
Plan your trip for the off-peak season and you're likely to score cheap Port Chester vacation packages. Bear in mind that public holidays and local events and festivals can have an impact on prices, so do your research before booking.
How many days is enough for Port Chester?
To fully enjoy your Port Chester vacation, we suggest booking for 2 days. Split your time between discovering Greenwich Point Park, Doral Arrowwood Golf Club and other major sights, in addition to experiencing neighbourhoods like Greenwich Municipal Centre Historic District and Strickland Road Historic District. If you've got some time to spare, include a day trip or tour in your Port Chester vacation itinerary.
Is it worth booking a vacation package to Port Chester?
Port Chester has everything you need for an amazing escape. Get your Port Chester vacation off to a flying start by exploring major attractions like Capitol Theatre.
How to find the best Port Chester package deals?
Start your search for a Port Chester package deal by entering your travel dates and destination under our "Packages" tab. Then select some filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Port Chester package deal right away, just switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Port Chester adventure off to a flying start.
Is it cheaper to book a Port Chester vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking stays and flights individually. Better still, you can tailor your Port Chester escape to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Port Chester?
If you're planning a spontaneous Port Chester trip, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find amazing deals on your hotels and flights by booking well in advance.
How to plan a trip to Port Chester?
- Choose when to get away: Check your diary and get your bags packed. Your favourite time of year and the available activities will also help you decide when to vacation in Port Chester.
- Calculate your budget: Ensure you have enough money to cover everything from transportation and food to experiences and flights. Your accommodations will probably be the biggest expense during your trip to Port Chester.
- Decide your trip length: Think about how much time you want to spend exploring Port Chester. Plan your days so you can get to all the experiences and attractions you're interested in at a comfortable pace.
- Bundle your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to find a Port Chester vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
