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.
Eurostars Wall Street

Eurostars Wall Street

4 out of 5
Manhattan
Price was CA $1,833, price is now CA $1,106 per person
CA $1,106
per person
Jan 12 - Jan 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
8/10 Very good! (1,000 reviews)
The best part of this hotel is the proximity and the size of the room. Hotel staff really hands-off, no amenities. Hotel very out dated and kind of dingy looking.

Reviewed on Nov 6, 2026

The St. Regis New York

The St. Regis New York

5 out of 5
Manhattan
Price was CA $2,486, price is now CA $1,336 per person
CA $1,336
per person
Jan 15 - Jan 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (293 reviews)
The managers need complete retraining or higher managers that are way more capable in dealing with customers and not fighting and arguing with them and telling them they’re wrong

Reviewed on Nov 6, 2026

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was CA $2,502, price is now CA $1,381 per person
CA $1,381
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was CA $4,252, price is now CA $2,495 per person
CA $2,495
per person
Dec 20 - Dec 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (4,080 reviews)

Eurostars The Chemists’ Club Hotel

Eurostars The Chemists’ Club Hotel

4 out of 5
Manhattan
Price was CA $2,738, price is now CA $1,620 per person
CA $1,620
per person
Jan 10 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to New York (JFK)
9.4/10 Exceptional! (555 reviews)

Ready to book your vacation to Port Chester?

 

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Port Chester Hotel Deals

Highbridge Hotel

Highbridge Hotel

2 out of 5
1263 Edward L Grant Highway Bronx NY
Fully refundableReserve now, pay when you stay
The price is CA $102 per night from Nov 29 to Nov 30
CA $102
CA $122 total
Nov 29 - Nov 30
includes taxes & fees
Highbridge Hotel
Radio Hotel

Radio Hotel

4 out of 5
2420 Amsterdam Ave New York NY
Fully refundableReserve now, pay when you stay
The price is CA $200 per night from Nov 9 to Nov 10
CA $200
CA $272 total
Nov 9 - Nov 10
includes taxes & fees
8.4/10 Very good! (2,341 reviews)
"Everything was great. The facility was simple but amazing. It had everything we needed for our trip. Would definitely be coming back to this hotel for future trips."

Reviewed on Nov 6, 2026

Radio Hotel
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
The price is CA $200 per night from Nov 10 to Nov 11
CA $200
CA $235 total
Nov 10 - Nov 11
includes taxes & fees
Four Points by Sheraton Flushing
See all 1,677 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.
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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.
See properties

What to do in Port Chester

Helicopter landing in a field in New York

Introductory Helicopter Flight Lesson from Westchester

CA $997
per traveller
Introductory Helicopter Flight Lesson from Westchester
See all activities in Port Chester

Frequently asked questions

How much does a Port Chester vacation package cost?
Offering great value package deals from CA $1,106 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.