Chester Holidays from £897

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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.
Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
Price was £1,156, price is now £897 per person
£897
per person
10 Sept - 14 Sept
found 1 day ago
Return direct flight included
London (LON) to Pittsburgh (PIT)
8/10 Very good! (302 reviews)
Affordable

Reviewed on 4 Jul 2026

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

4 out of 5
Downtown Pittsburgh
Price was £1,209, price is now £1,004 per person
£1,004
per person
10 Sept - 14 Sept
found 1 day ago
Return direct flight included
London (LON) to Pittsburgh (PIT)
8.2/10 Very good! (1,074 reviews)
I didn't have any major problems with my room I couldn't solve by going to speak to the front desk. But items such as: Not having a refrigerator, telephone not working were bit of an annoyance since those are some amenities that "should" be prepared upon check in. Whether or not "remodeling" was part of the problem ( as what I was told ), I just felt my room was a little unprepared, but nothing I couldn't work with. Overall, I'd give my experience about a 7/10.

Reviewed on 7 Jul 2026

TRYP by Wyndham Pittsburgh/Lawrenceville

TRYP by Wyndham Pittsburgh/Lawrenceville

3 out of 5
Lawrenceville
Price was £1,056, price is now £909 per person
£909
per person
10 Sept - 14 Sept
found 1 day ago
Return direct flight included
London (LON) to Pittsburgh (PIT)
8.6/10 Excellent! (1,012 reviews)
Clean modern convenient location

Reviewed on 8 Jul 2026

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was £1,048, price is now £905 per person
£905
per person
10 Sept - 14 Sept
found 1 day ago
Return direct flight included
London (LON) to Pittsburgh (PIT)
8.6/10 Excellent! (146 reviews)
Loved the historic building. This was a great place to stay in downtown. However, the parking was a bit confusing.

Reviewed on 8 Jul 2026

Hilton Garden Inn Pittsburgh Downtown

Hilton Garden Inn Pittsburgh Downtown

3 out of 5
Downtown Pittsburgh
Price was £1,420, price is now £1,232 per person
£1,232
per person
10 Sept - 14 Sept
found 1 day ago
Return direct flight included
London (LON) to Pittsburgh (PIT)
9/10 Wonderful! (1,387 reviews)
The hotel was in a perfect location for walking to the PNC Park

Reviewed on 4 Jul 2026

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 2 bed, 1.5 bath

The Piedmont Cabin 2 bed, 1.5 bath

Chester WV
10/10 Exceptional! (7 reviews)
"Beautiful little cabin. Gorgeous flooring! Super peaceful!"

Reviewed on 11 Jun 2026

Get rates
The Piedmont Cabin 2 bed, 1.5 bath
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 £68 per night from 29 Jul to 30 Jul
£68
29 Jul - 30 Jul
includes taxes & fees
8.2/10 Very good! (2,341 reviews)
"Shuttle service.to the Airport was 15 minutes late on the first run of the day. Staff did not know how the shuttle service reservation system worked. Had to catch a Uber."

Reviewed on 8 Jul 2026

La Quinta Inn by Wyndham Pittsburgh Airport
Hyatt Regency Pittsburgh International Airport

Hyatt Regency Pittsburgh International Airport

3.5 out of 5
710 Aviation Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is £144 per night from 12 Jul to 13 Jul
£144
12 Jul - 13 Jul
includes taxes & fees
9/10 Wonderful! (1,704 reviews)
"It’s near the airport and that’s the only reason to stay here. It’s noisy and smells. Staff is not helpful or friendly. There is airport shuttle. They were nice."

Reviewed on 8 Jul 2026

Hyatt Regency Pittsburgh International Airport
See all 172 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

Stay near popular Chester attractions

Mountaineer Casino Resort

7.8/10 (118 reviews)
This all-in-one entertainment venue combines thrilling casino gaming with live thoroughbred racing in West Virginia. Enhance your visit with a round on the championship golf course or rejuvenate at the full-service spa.
See properties

Frequently asked questions

How much does a Chester travel package cost?
Our Chester travel packages, which begin at just £897, 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.

Explore a world of travel with Expedia

* 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.