Port Chester Holidays from £1,127

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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.
Sound View Greenport

Sound View Greenport

4 out of 5
Save 100% on your flight
per person
14 Sept - 21 Sept
found 1 day ago
Return flight included
London (LGW) to New York (JFK)
8.4/10 Very Good! (532 reviews)
We stayed here for an overnight for a girls trip with my 8yr old daughter, we had the best time. We will be back!

Reviewed on 30 Jul 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
per person
3 Sept - 10 Sept
found 18 hours ago
Return flight included
London (LGW) to New York (JFK)
8.8/10 Excellent! (1,006 reviews)
Nice views.. but food at restaurant left a lot to be desired. Also staff presentation was terrible. They need uniforms and a dress code. Booty shorts, wrinkled clothing... its all a part of the experience and everyone looked like they got up out of bed and came to work. Take pride. Its managements fault ..

Reviewed on 30 Jul 2025

The Pierre, A Taj Hotel, New York

The Pierre, A Taj Hotel, New York

5 out of 5
Manhattan
Save 100% on your flight
per person
9 Sept - 14 Sept
found 1 day ago
Return flight included
London (LHR) to New York (JFK)
9.2/10 Wonderful! (1,000 reviews)
Staff went out of their way to be courteous and polite

Reviewed on 30 Jul 2025

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
per person
16 Oct - 23 Oct
found 1 day ago
Return direct flight included
London (LHR) to New York (JFK)
9.2/10 Wonderful! (1,003 reviews)
Exceedingly above my expectations

Reviewed on 31 Jul 2025

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Save 100% on your flight
per person
9 Oct - 15 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to New York (JFK)
9/10 Wonderful! (2,098 reviews)
Very convenient location in Manhattan. Room was clean, modern designed hotel.

Reviewed on 29 Jul 2025

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

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 £105 per night from 3 Aug to 4 Aug
£105
3 Aug - 4 Aug
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
"It was clean and nice"

Reviewed on 27 Jul 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 £137 per night from 3 Aug to 4 Aug
£137
3 Aug - 4 Aug
includes taxes & fees
8.6/10 Excellent! (2,607 reviews)
"Last minute stayed extended was available and receptionist made a smooth possible changed. Thanks"

Reviewed on 26 Jul 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 £119 per night from 4 Aug to 5 Aug
£119
4 Aug - 5 Aug
includes taxes & fees
8.8/10 Excellent! (1,553 reviews)
"Further from airport than stated in internet. Clean and quiet and helpful staff."

Reviewed on 31 Jul 2025

Ly New York Hotel
See all 1,614 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

Popular places to visit

Doral Arrowwood Golf Club

Enjoy a round of golf in Rye Brook at Doral Arrowwood Golf Club. Visit the shops and top-notch restaurants in this romantic area.

Doral Arrowwood Golf Club

What to do in Port Chester

LEGOLAND® Discovery Center Westchester Tickets

LEGOLAND® Discovery Center Westchester Tickets

£24
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

£699
per traveller
Couple's Private NYC Helicopter Tour from Westchester
Helicopter landing in a field in New York

Introductory Helicopter Flight Lesson from Westchester

£493
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 £1,127. 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.