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.
La Quinta Inn & Suites by Wyndham Secaucus Meadowlands

La Quinta Inn & Suites by Wyndham Secaucus Meadowlands

3 out of 5
Save 100% on your flight
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
7/10 Good! (2,096 reviews)
Staff was friendly. Room was clean.

Reviewed on Jul. 12, 2025

Sound View Greenport

Sound View Greenport

4 out of 5
per person
Aug 28 - Sep 4
just found
Roundtrip flight included
Montreal (YUL) to New York (JFK)
8.4/10 Very Good! (531 reviews)
Right on the water. Private beach with chair and umbrellas.they will serve you right on the beach bye getting you food and drinks also has a outdoor swimming pool..nice staff..nothing special about the continental breakfast..bagels, fruit, small croissants, small danish and some hard boiled eggs..coffee and oj..i was pleased with my stay. King deluxe room..small table with chairs on the shared deck..could sit outside til about 2pm and the sun starts to beat on you but no biggy..was very humid out when my wife and i was there..a/ c really could not cool the room as much as we would have liked. Nothing wrong with the a/c it just because the sun beating on the hotel all day..luckily i brought a couple of small usb fans to help keep cool at night while we slept did the trick..overall i enjoy my stay and you could not ask for anything more when it comes to the scenery..

Reviewed on Jul. 10, 2025

The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
Save 100% on your flight
per person
Aug 28 - Sep 4
just found
Roundtrip flight included
Montreal (YUL) to New York (JFK)
8.8/10 Excellent! (474 reviews)
This hotel is a pure gem. The service is fantastic, the front desk team works to make sure you are truly taken care of, including our dog. Very calm vibe, its super clean, quiet and perfect. Already looking at another couple of nights in August!

Reviewed on Jul. 11, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
per person
Sep 13 - Sep 16
just found
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,004 reviews)
What a great place! The location was fantastic, the staff was great, and the views were unbelievable. Definitely want to come back some day!

Reviewed on Jul. 12, 2025

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
per person
Sep 17 - Sep 23
found 5 hours ago
Roundtrip flight included
Toronto (YTZ) to New York (JFK)
9/10 Wonderful! (1,009 reviews)
Staff are fantastic!

Reviewed on Jul. 7, 2025

Ready to book your vacation to Port Chester?

 

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Port Chester Hotel Deals

EVEN Hotel Norwalk by IHG
EVEN Hotel Norwalk by IHG
3.5 out of 5
426 Main Ave, Route 7, Norwalk, CT
Fully refundable
The price is CA $148 per night from Aug 4 to Aug 5
CA $148
CA $170 total
Aug 4 - Aug 5
includes taxes & fees
8.2/10 Very Good! (1,007 reviews)
"Everything!"

Reviewed on Jul. 12, 2025

EVEN Hotel Norwalk by IHG
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 Jul 22 to Jul 23
CA $186
CA $248 total
Jul 22 - Jul 23
includes taxes & fees
8.6/10 Excellent! (2,577 reviews)
"Property was perfectly fine. It was rather small but that's what you expect I suppose in Manhattan. It was a weird thing where we had to buy two drinks for $22 to get the hotel room. I would have preferred not to have had the drink. The bed was comfortable everything was adequate. We were close to ..."

Reviewed on Jul. 4, 2025

Radio Hotel
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 $159 per night from Jul 14 to Jul 15
CA $159
CA $187 total
Jul 14 - Jul 15
includes taxes & fees
8.8/10 Excellent! (1,464 reviews)
"room is clean, quiet, the continental breakfast should be improved. over all was good hotel"

Reviewed on Jul. 9, 2025

Ly New York Hotel
See all 1,606 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

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

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
Couple's Private New York Helicopter Tour from Westchester

Couple's Private NYC Helicopter Tour from Westchester

CA $1,304
per traveller
Couple's Private NYC Helicopter Tour from Westchester
Helicopter landing in a field in New York

Introductory Helicopter Flight Lesson from Westchester

CA $920
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 $462 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.