Port Chester Holidays from £818

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Your Port Chester Holiday

When a city getaway is calling, answer it with a holiday package to Port Chester. The neighbourhood 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 Centre Gallery. Stop daydreaming and start travelling. Browse the wide range of options on Expedia today and put your Port Chester holiday plans into gear!

Top Port Chester Flight + Hotel Deals

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
Price was £1,256, price is now £818 per person
£818
per person
21 Jan - 24 Jan
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
8.8/10 Excellent! (1,001 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 19 Oct 2026

The St. Regis New York

The St. Regis New York

5 out of 5
Manhattan
Price was £2,829, price is now £1,656 per person
£1,656
per person
22 Jan - 26 Jan
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (293 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 £3,309, price is now £1,970 per person
£1,970
per person
1 Dec - 5 Dec
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (4,080 reviews)
Excelente ubicación, muy buen hotel.

Reviewed on 29 Oct 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was £2,538, price is now £1,512 per person
£1,512
per person
21 Jan - 27 Jan
found 1 day ago
Return flight included
London (LHR) to New York (JFK)
9/10 Wonderful! (1,004 reviews)

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 £3,282, price is now £1,961 per person
£1,961
per person
1 Dec - 5 Dec
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9/10 Wonderful! (3,435 reviews)
Too loud and too expensive for what it is... The doorman chases you as you enter the. Building

Reviewed on 29 Oct 2026

Port Chester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
John F. Kennedy Intl. Airport (JFK)
Population
29,600
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Capitol Theatre, Stamford Centre for the Arts and West Beach

Top hotels in Port Chester

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 £80 per night from 2 Nov to 3 Nov
£80
2 Nov - 3 Nov
includes taxes & fees
9.2/10 Wonderful! (4,344 reviews)
"2 night stay. Location was great. Room was clean & nice for a reasonable price! The continental breakfast was good as well. We will be back :)"

Reviewed on 29 Oct 2026

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 £136 per night from 2 Nov to 3 Nov
£136
2 Nov - 3 Nov
includes taxes & 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
The price is £102 per night from 1 Nov to 2 Nov
£102
1 Nov - 2 Nov
includes taxes & fees
Executive Inn - Fort Lee
See all 1,758 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

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.
See properties

What to do in Port Chester

Helicopter landing in a field in New York

Introductory Helicopter Flight Lesson from Westchester

£526
per traveller
Introductory Helicopter Flight Lesson from Westchester
See all activities in Port Chester

Frequently asked questions

How much does a Port Chester travel package cost?
We make it simple to explore the world, with Port Chester packages starting from just £818. You'll have the flexibility to bundle your favourite airlines, hotels and car rental. For the ultimate escape, why not add some tours and experiences to your itinerary?
If I'm not able to travel, can I cancel my Port Chester travel package?
We totally understand — unexpected stuff happens. If you've booked a Port Chester travel package and need to cancel or change it, we're here to help. It's always worth looking up our Customer Service Portal first for information. But generally, if you've taken out your package within 24 hours, you may be able to cancel or amend your itinerary for free. If it's more than 24 hours, your airline, hotel or car rental company may charge a fee.
How do I get a cheap travel package to Port Chester?
Bundle your flights and hotels, add on extras such as activities or a rental car, and save with a Port Chester holiday package. You won't just walk away with exciting discounts on your escape — you'll have a world of choice within your reach too. When you book with Expedia, you can choose from more than 550 air carriers and 1,000,000 hotels around the world. Your next grand adventure starts right here, right now!
Does Expedia offer Book Now, Pay Later Port Chester holidays?
Yes, we do. Expedia has partnered with online lender Klarna to help you easily pay for your trip in manageable instalments. Simply click on the payment plan that suits you best during checkout and take the stress out of budgeting for your trip. Be sure to bundle your flights, accommodation and car hire with Expedia to get the biggest bang for your buck. Take a look at our flexible payment options below:

  • Pay monthly holidays: Jet off on that dream holiday sooner with Klarna's monthly instalment plans. If paying just a small amount each month works for you, choose this option at checkout.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna allows you to pay off your trip in multiple transactions.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the full total upfront) makes it easier to hit that "book now" button, consider a low deposit holiday payment plan from Klarna.

Where should I stay in Port Chester?
It makes sense to stay near the action. Many travellers like to book hotels within easy reach of popular attractions, like Capitol Theatre, Doral Arrowwood Golf Club and Clay Art Centre Gallery.
What are the top hotels in Port Chester?
Make a reservation at Courtyard by Marriott Rye. It's one of the neighbourhood's most popular properties. Another great option in Port Chester is Historic Castle 1876 13 Mins To Wing Foot Cc Border Of Greenwich And New York.
How far in advance should I book my Port Chester holiday?
Be rewarded with the biggest variety and the lowest prices by booking your holiday to Port Chester nice and early. Air carriers typically publish flight tickets around a year in advance, so start your planning as soon as you can. Having said that, Expedia is dedicated to providing you with the best deals around, so it's always a good time to book your dream holiday!
What does an Expedia Port Chester travel package include?
Flights, hotels and a shiny set of wheels for all your road trip adventures. Simply select your preferred bundle and get access to great discounts. Once you've made your booking, add on a few activities and tours and watch your savings grow. When it comes to creating your Port Chester holiday, you're in charge!
What should I know before booking a Port Chester travel package?
You'll save big with an Expedia travel package. Bundle your airfares, rental cars and hotels and be rewarded with great discounts. Hotels aren't your only choice, though. We've got island villas, cosy city apartments and just about everything in between!
Can I choose my airline with a Port Chester Expedia travel package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines around the world. Our packages give you the flexibility to take your pick of available flight, hotel or activity options that suit you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.