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.
Night Hotel Broadway
Manhattan
CA $899
per person
Nov 25 - Nov 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
7.6/10 Good! (3,584 reviews)
This is an old hotel in NYC, so it has small rooms and is a bit funky but we really liked it. The rooms were clean. There was a pedestal sink in the bathroom (nice tile) so they had added a shelf for toiletries. The hot water was was a bit slow getting to the the 12th floor but it warmed up pretty quickly. The wall outlets were old and too loose for a phone charger but there was a charging station on the desk that works beautifully. The staff was extremely helpful and really seemed to want to make sure guests enjoyed their stay. The location is great. You can easily go to 96th street and catch a crosstown bus or an subway to go down or uptown. We would definitely consider staying there again.
Reviewed on Sep 23, 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 $321
CA $412 total
Oct 25 - Oct 26
includes taxes & fees
8.4/10 Very good! (2,418 reviews)
"The hotel was really lackluster"
Reviewed on Sep 24, 2026
DoubleTree by Hilton Fort Lee - George Washington Bridge
2117 Route 4 Eastbound Fort Lee NJ
Fully refundableReserve now, pay when you stay
CA $207
CA $237 total
Oct 25 - Oct 26
includes taxes & fees
8/10 Very good! (1,196 reviews)
"Definitely recommend. Staff was very nice and helpful. Room was very clean and spacious. Parking was easy."
Reviewed on Sep 24, 2026
Tarrytown House Estate
49 E Sunnyside Lane Tarrytown NY
Fully refundableReserve now, pay when you stay
CA $219
CA $301 total
Sep 27 - Sep 28
includes taxes & fees
8.2/10 Very good! (1,316 reviews)
"It’s a beautiful property. It’s about a mile walk to the closest off property restaurants. It’s a historic town where everyone drives so it’s a bit like frogger."
Reviewed on Sep 24, 2026
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 $1,818
per traveller
Frequently asked questions
How much does a Port Chester vacation package cost?
Offering great value package deals from CA $899 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.
