Chester Holidays from £885

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Photo by Bill Dillard

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    Save up to £335 when you book a flight and hotel together*
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    Packages with flights are ATOL protected

Your Chester Holiday

Our holiday packages to Chester give you endless opportunities to delve into new sights, sounds and experiences. And with all the finer details worked out, you can breathe easy and enjoy your city escape to the fullest. You'll want to do some exploring during your trip to Chester. Carve out some time for famous attractions like Mountaineer Casino, The Mountaineer Race Track & Gaming Resort and Tomlinson Run State Park. A few clicks is all it takes to create the perfect Chester holiday on Expedia.

Top Chester Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
per person
4 Oct - 11 Oct
found 1 hour ago
Return direct flight included
London (LHR) to Pittsburgh (PIT)
8.4/10 Very Good! (1,334 reviews)
We checked in Friday and got to our room and found out it was compact room. Which means it was a very small room with minimal walking room. It was nice, however, for the price we paid per night I would have booked somewhere else and had actual space to open our suitcase somewhere other than on the bed. The pictures on both Expedia and the Joinery website were deceiving. We also went for supper in the restaurant Friday night which only had a bar tender and two cooks working. The bar tender was over run and because of that, the service was less than satisfactory. Our meals came out fairly quickly but the two steaks were cold and options of sides were not given. For a Friday evening they should have adaquate staff to run smoothly.

Reviewed on 11 Aug 2025

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Save 100% on your flight
per person
4 Oct - 11 Oct
found 1 hour ago
Return direct flight included
London (LHR) to Pittsburgh (PIT)
7.6/10 Good! (12 reviews)
This unique property is perfectly located. Within walking distance to bars, restaurants, and shops. Check in was flawless. We stayed one night but, This property has everything needed for long term stays.

Reviewed on 11 Aug 2025

Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
per person
4 Oct - 11 Oct
found 1 hour ago
Return direct flight included
London (LHR) to Pittsburgh (PIT)
7.8/10 Good! (160 reviews)
Very nice building: apartment needed TLC but all & all nice stay!

Reviewed on 10 Aug 2025

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
per person
4 Oct - 11 Oct
found 1 hour ago
Return direct flight included
London (LHR) to Pittsburgh (PIT)
8.6/10 Excellent! (1,002 reviews)
Location, location, location. The property layout is super convenient with easy access to the convention center and local amenities. Like many properties, I felt the room was not as updated and fresh as the public areas were. Check-in was extremely fast and efficient. The value is in the proximity to the freeway and downtown life.

Reviewed on 22 Jun 2025

Hilton Garden Inn Pittsburgh Downtown

Hilton Garden Inn Pittsburgh Downtown

3 out of 5
Downtown Pittsburgh
per person
4 Oct - 11 Oct
found 1 hour ago
Return direct flight included
London (LHR) to Pittsburgh (PIT)
9/10 Wonderful! (1,015 reviews)
Liked the convenience of the property. Close to all the places I wanted to be.

Reviewed on 11 Aug 2025

Chester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Pittsburgh Intl. Airport (PIT)
Population
2,500
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Mountaineer Casino and The Mountaineer Race Track & Gaming Resort

Top hotels in Chester

The Piedmont Cabin - LPM

The Piedmont Cabin - LPM

2 out of 5
Chester, WV
The price is £153 per night from 17 Aug to 18 Aug
£153
17 Aug - 18 Aug
includes taxes & fees
The Piedmont Cabin - LPM
The Auburn Home - LPM

The Auburn Home - LPM

2 out of 5
Chester, WV
The price is £197 per night from 17 Aug to 18 Aug
£197
17 Aug - 18 Aug
includes taxes & fees
10/10 Exceptional! (8 reviews)
"Clean, spacious, as advertised"

Reviewed on 23 Jul 2025

The Auburn Home - LPM
La Quinta Inn by Wyndham Pittsburgh Airport

La Quinta Inn by Wyndham Pittsburgh Airport

3 out of 5
8507 University Blvd, Coraopolis, PA
Fully refundableReserve now, pay when you stay
The price is £67 per night from 24 Aug to 25 Aug
£67
24 Aug - 25 Aug
includes taxes & fees
7.8/10 Good! (2,022 reviews)
"Very nice. Some lamps were not working."

Reviewed on 9 Aug 2025

La Quinta Inn by Wyndham Pittsburgh Airport
See all 134 properties in 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

Frequently asked questions

How much does a Chester travel package cost?
Our Chester travel packages, which begin at just £885, are the perfect way to save big. Choose your preferred hotels, flights and rental car to create a personalized trip.
If I'm not able to travel, can I cancel my Chester travel package?
Your situation can change suddenly, so yes, you can. You may be able to amend or cancel your Chester travel package at no cost within 24 hours of booking. For older bookings, you can still cancel and rebook, but your airline, hotel or car rental company may impose a fee. Want more information? Look up our Customer Service Portal. We'll help make sure your trip goes off without a hitch.
How do I get a cheap travel package to Chester?
One of the simplest ways to save dollars (and time) is to bundle your bookings with Expedia. Hotels, flights, activities and rental cars — we've got them all covered. Pick a combination that best fits you and see your savings pile up. We know a package deal is never a one-size-fits-all. That's why Expedia offers over 550 air carriers and 1,000,000 properties worldwide, which lets you customize your Chester adventure.
Does Expedia offer Book Now, Pay Later Chester holidays?
Your bank balance shouldn't prevent you from taking a holiday, so Expedia has come up with a solution to help. Thanks to our partnership with online lender Klarna, it's easier than ever to book a terrific getaway without eating away at your savings. Klarna offers flexible payment options during the checkout process that take the stress out of budgeting for your escape. Consider one of these flexible payment options:

  • Pay monthly holidays: Klarna offers convenient monthly payment plans that fit all budgets, so you can escape on that well-deserved holiday sooner.
  • Pay in instalments holidays: Into the idea of paying down your holiday in multiple transactions? Then go for this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: When you see an incredible deal but your budget doesn't quite cover it yet, Klarna's low deposit holiday plan will help you secure your getaway.

Where should I stay in Chester?
There's so much to see in Chester, so spend your evenings close to its best sights and maximize your time sightseeing. The Mountaineer Race Track & Gaming Resort is one place that should be on your itinerary.
What are the top hotels in Chester?
Mountaineer Casino, Racetrack & Resort and Holiday Inn Exp Chester WV, an IHG Hotel are among the most sought-after properties in Chester. Why not check out the facilities and rates at each and then decide?
How far in advance should I book my Chester holiday?
To score rock-bottom prices, book early. Airlines usually advertise flights, along with some of the lowest fares, around a year in advance. Hotels, activities and car rental should also be booked well in advance so you can have the pick of the bunch. If you're in need of a last-minute getaway in Chester, there are always lots of great deals to be had on Expedia. Book something in today!
What does an Expedia Chester travel package include?
It comes down to what you want. If you're travelling by yourself, you might decide to bundle flights and hotels. Bringing the entire family to Chester? A travel package including rental cars, flights and hotels might be a better fit. Expedia gives you the flexibility and freedom to tailor-make your travel package.
What should I know before booking a Chester travel package?
Locking in all the parts of your escape together is a smart way to save. Bundle your flights, car rentals and hotels into a neat little package. But you're not restricted to hotels. Expedia features all types of properties, including holiday rentals such as oceanfront condos and city residences. You've got choices galore!
Can I choose my airline with a Chester Expedia travel package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines around the world. Our packages give you the flexibility to pick from available flights, hotels and activities 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.