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.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was CA $1,179, price is now CA $697 per person
CA $697
per person
Oct 6 - Oct 9
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.2/10 Wonderful! (1,003 reviews)
Very large room, well maintained hotel, friendly helpful staff.

Reviewed on Aug. 25, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $3,736, price is now CA $2,074 per person
CA $2,074
per person
Oct 28 - Oct 31
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,009 reviews)
Wonderful room and staff. The Brooklyn Bridge view was amazing.

Reviewed on Aug. 21, 2025

Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Manhattan
Price was CA $1,365, price is now CA $837 per person
CA $837
per person
Oct 1 - Oct 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (2,296 reviews)
Good option to stay in NYC

Reviewed on Aug. 27, 2025

New York Marriott Marquis

New York Marriott Marquis

4.5 out of 5
Manhattan
Price was CA $1,611, price is now CA $998 per person
CA $998
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (3,915 reviews)
Breakfast was awesome

Reviewed on Aug. 28, 2025

Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
Price was CA $1,549, price is now CA $961 per person
CA $961
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (6,263 reviews)
The hotel was good and the staff were so nice. I would go again!

Reviewed on Aug. 27, 2025

Ready to book your vacation to Port Chester?

 

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Port Chester Hotel Deals

Ly New York Hotel

Ly New York Hotel

2.5 out of 5
15-61 127th St, College Point, NY
Fully refundableReserve now, pay when you stay
The price is CA $197 per night from Sep 7 to Sep 8
CA $197
CA $252 total
Sep 7 - Sep 8
includes taxes & fees
Ly New York Hotel
Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

3 out of 5
200 West Main Street, Elmsford, NY
Fully refundableReserve now, pay when you stay
The price is CA $189 per night from Sep 7 to Sep 8
CA $189
CA $216 total
Sep 7 - Sep 8
includes taxes & fees
7.8/10 Good! (1,137 reviews)
"The entrance and outside decor needs to be updated."

Reviewed on Aug. 25, 2025

Hampton Inn White Plains/Tarrytown
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 $186 per night from Sep 28 to Sep 29
CA $186
CA $249 total
Sep 28 - Sep 29
includes taxes & fees
Radio Hotel
See all 1,622 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.
All Inclusive Vacations
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Discover the most popular places to visit in Port Chester

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

CA $42
per adult
76% of travellers recommend
LEGOLAND® Discovery Center Westchester Tickets
Helicopter landing in a field in New York

Introductory Helicopter Flight Lesson from Westchester

CA $922
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 $697 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.