Chester Holidays

Photo by Bill Dillard
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    Better together
    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Chester

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 S$122 per night from 7 Jul to 8 Jul
S$122
7 Jul - 8 Jul
includes taxes & fees
7.8/10 Good! (1,967 reviews)
"Everything was as advertised"

Reviewed on 26 Jun, 2025

La Quinta Inn by Wyndham Pittsburgh Airport
Wyndham Garden Pittsburgh Airport
Wyndham Garden Pittsburgh Airport
3 out of 5
1 Industry Lane, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is S$128 per night from 6 Jul to 7 Jul
S$128
6 Jul - 7 Jul
includes taxes & fees
6.6/10 (1,006 reviews)
Ok for the price
"The stay was great and gentleman at the front desk during check in was amazing! The only disappointment was the breakfast, no hot items and could only be categorized as minimalist at best"

Reviewed on 29 Jun, 2025

Wyndham Garden 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 S$288 per night from 4 Jul to 5 Jul
S$288
4 Jul - 5 Jul
includes taxes & fees
9/10 Wonderful! (1,481 reviews)
"Convenient to airport"

Reviewed on 27 Jun, 2025

Hyatt Regency Pittsburgh International Airport
See all 132 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.

Frequently asked questions

How much does a Chester holiday package cost?
You can grab a holiday package to this top destination on Expedia. However, how much your holiday to Chester costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Chester?
To pick up cheap Chester holiday packages, organise your getaway outside of busy periods such as school holidays. You'll generally find better availability and lower prices for hotels and flights.
How many days is enough for Chester?
The ideal length for your Chester holiday depends on what you'd like to see and do. Generally, a few days to a week will give you time to check out all the leading attractions and explore some hidden treasures along the way.
How to find the best Chester package deals?
Use Expedia's filter tool to help you find some great Chester package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or search for Chester package deals in the off-peak season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to book your holiday package well in advance.
Is it cheaper to book a Chester holiday as a package?
Expedia holiday packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll usually snag a better deal than booking each component individually. And you'll still enjoy the freedom to create a personalised Chester holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday package to Chester?
If you're planning a spontaneous Chester getaway, check out our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can find amazing deals on your flights and hotels by booking ahead.
How to plan a trip to Chester?

  1. Pick the ideal time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to visit Chester.
  2. Plan your budget wisely: Besides the price of your hotel, you should factor in other expenses. These include transportation, flights and food. Also, put aside a little extra for unexpected costs that could crop up during your trip to Chester.
  3. Decide how long to go away for: Now that you know more about Chester, you can figure out the right length of your holiday. Create a draft itinerary and allocate enough time to cover everything you want to see.
  4. Bundle your airfare and accommodation: Once you've nailed down your travel dates and duration, book the ideal Chester holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.