Port Chester Vacations from $924

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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!

The Latest Port Chester vacation packages

Price found within the past 48 hours. Click for updated prices.
JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Save 100% on your flight
Price was $1,728, price is now $924 per person
$924
per person
Jan 7 - Jan 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,004 reviews)
We had an incredible stay at the Essex House last week with our two kids (one is 7 and the other turned 4 on our trip). We booked the king suite, thinking that even though it's NYC and the room will likely be small, it would be the best option for a family of 4. We were SHOCKED at the size of the suite! Not only was it enough room for all of us, it was downright roomy! We had plenty of space for our stay. The amenities and cleanliness of the hotel are superior, room service was delicious (if expensive), and best of all...the guest relations team sent a special surprise gift to our room for our 4 year olds birthday. They sent him balloons, two pieces of cake, and a bag full of stuffies and goodies. He was THRILLED and we were so touched by the thoughtfulness. Both of our kids have already asked if - not only can we go back to New York - but can we stay at the Essex House again! The location was incredible and overall the Essex House played a big part in how wonderful and effortless our trip was. Already looking at dates in the Spring to visit again! Thank you Essex House and your wonderful staff!

Reviewed on Oct 19, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was $3,955, price is now $1,938 per person
$1,938
per person
Dec 29 - Jan 3
found 18 hours ago
Roundtrip flight included
Los Angeles (LAX) to New Haven (HVN)
No reviews

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $2,621, price is now $1,512 per person
$1,512
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (4,080 reviews)
Location, location, location! The staff was outstanding. The rooms were updated and clean.

Reviewed on Oct 27, 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $2,604, price is now $1,503 per person
$1,503
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (3,435 reviews)

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
Price was $3,263, price is now $1,998 per person
$1,998
per person
Dec 28 - Jan 2
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (1,002 reviews)
Great location; great service. Seemed to be a problem with the room heat/AC, but the weather was mild in NYC that week, so I cannot fully confirm.

Reviewed on Oct 26, 2026

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Stay near popular Port Chester attractions

Capitol Theatre

7.4/10 (117 reviews)
This historic venue captivates with exceptional acoustics and intimate performances from renowned artists. Arrive early to enjoy the theater's vintage architecture and pre-show ambiance in the stylish lounge areas.
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What to do in Port Chester

Sleepy Hollow Ghost Tour

Sleepy Hollow Ghost Tour (Self-Guided Audio Driving/Walking Tour)

$10
per adult
Sleepy Hollow Ghost Tour (Self-Guided Audio Driving/Walking Tour)
See all activities in Port Chester

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
$120 nightly
The price is $141 total per night from Oct 29 to Oct 30
$141 total
Oct 29 - Oct 30
Total with taxes and fees
9.2/10 Wonderful! (4,337 reviews)
"Great breakfast! Rooms were decent and very friendly staff!"

Reviewed on Oct 27, 2026

Highbridge Hotel
Radio Hotel

Radio Hotel

4 out of 5
2420 Amsterdam Ave New York NY
Fully refundableReserve now, pay when you stay
$178 nightly
The price is $207 total per night from Nov 22 to Nov 23
$207 total
Nov 22 - Nov 23
Total with taxes and fees
Radio Hotel
Executive Inn - Fort Lee

Executive Inn - Fort Lee

3.5 out of 5
2339 Route 4 Fort Lee NJ
Fully refundableReserve now, pay when you stay
$124 nightly
The price is $142 total per night from Oct 28 to Oct 29
$142 total
Oct 28 - Oct 29
Total with taxes and fees
8/10 Very Good! (1,591 reviews)
"We asked for a blanket or comforter because there were no covers in the room, asked for one they said they didn’t have any. Very uncomfortable stay."

Reviewed on Oct 26, 2026

Executive Inn - Fort Lee
See all 1,768 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.

Find the Best Port Chester Vacation Packages

Port Chester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
John F. Kennedy Intl. Airport (JFK)
Population
29,600
Top Sights
Capitol Theatre, Doral Arrowwood Golf Club and Clay Art Center Gallery

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Frequently asked questions

Is Port Chester better suited for a beach vacation or a cultural trip?
Port Chester is a central urban destination known for family-friendly attractions, offering a blend of cultural experiences and nearby coastal relaxation. It provides a mix of entertainment options, such as the historic Capitol Theatre and the Clay Art Center Gallery, which is about a 5-minute walk from central Port Chester.

For those seeking outdoor fun, Rye Playland is about 1 mile away, and several beaches like Rye Beach and Oakland Beach are within about 2 miles. A Port Chester vacation package can easily combine urban exploration with nearby coastal relaxation and family entertainment.
How can I save money on a Port Chester vacation package?
When you bundle, you can save up to 30%*. To save money on a Port Chester package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
What are the top things to do in Port Chester?
A Port Chester vacation offers a blend of entertainment, arts, and outdoor activities:

Browse and book things to do in Port Chester on Expedia.
Do you need to rent a car in Port Chester, or is public transport enough?
Public transportation is a viable option for getting around during your Port Chester vacation package, especially for reaching nearby cities. The Metro-North Railroad's Port Chester station provides commuter rail service to Grand Central Terminal in New York City, as well as Stamford and New Haven in Connecticut. Local bus services, including the Bee-Line Bus System and Connecticut Transit Stamford Division, also operate within the area. For more flexibility or to reach destinations not covered by public transit, local taxis and ride-share apps are readily available.

For travelers booking Port Chester vacation packages with flights, public transit can connect you to major hubs, while a car or taxi offers convenience for exploring the immediate Port Chester area and its attractions.
Are there vacation package hotels in Port Chester within walking distance of restaurants and shops?
A Port Chester vacation package can include hotels that offer convenient access to local restaurants and shops. While central Port Chester itself features walkable areas with attractions like the Clay Art Center Gallery about a 5-minute walk away, hotels like Courtyard by Marriott Rye are about 1 mile from the Capitol Theatre, an area often surrounded by dining and retail options. For a more upscale stay, the 4-star Delamar Greenwich Harbor, rated 9.5 out of 10, is about 3 miles from the Capitol Theatre, offering a short drive to the area's amenities.

Actual walking routes may differ from straight-line distances, so check the map for your selected hotel.
Can I change or cancel my Port Chester vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Port Chester vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Port Chester vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Port Chester vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Port Chester?
To find last-minute vacation packages to Port Chester, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Port Chester vacation packages?
Free cancellation on a Port Chester vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Port Chester vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Port Chester getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Port Chester vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.