Chester Vacations from $358

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Your Chester Vacation

Our vacation 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 vacation on Expedia.

The Latest Chester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hiland Terrace Hotel

Hiland Terrace Hotel

2 out of 5
North Huntingdon
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Pittsburgh (PIT)
4.8/10 (106 reviews)
First off, the staff was very gracious. The rooms were clean and the linens newer. The building could use some updating as the sidewalks are sinking a bit making it harder for those with mobility issues to get into their rooms. It also appears that most of the guests are transients workers, maybe in oil, which isn't an issue but they have different needs then visitors to an area. The rooms are small and my room did not have some of the items that my son's room had, like chairs

Reviewed on Dec 15, 2024

Super 8 by Wyndham Delmont

Super 8 by Wyndham Delmont

2 out of 5
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Pittsburgh (PIT)
7/10 Good! (568 reviews)
Good nites sleep. Clean enough but not fancy.

Reviewed on Apr 30, 2025

Super 8 by Wyndham New Stanton

Super 8 by Wyndham New Stanton

2 out of 5
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Pittsburgh (PIT)
8/10 Very Good! (1,003 reviews)
The entrance should be a little more noticeable and lit in the evening. For a super 8, this was better than expected. The room was clean, shower was hot, tv was nice, breakfast was nice, no complaints really

Reviewed on Apr 27, 2025

Days Inn by Wyndham Blairsville

Days Inn by Wyndham Blairsville

2.5 out of 5
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Pittsburgh (PIT)
7.6/10 Good! (450 reviews)
Very convenient. Many dining options nearby.

Reviewed on Apr 26, 2025

Slopeside Hotel by Seven Springs Resort

Slopeside Hotel by Seven Springs Resort

4.5 out of 5
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Pittsburgh (PIT)
8.8/10 Excellent! (263 reviews)
This hotel and staff are lovely, feels great! Lots of amenities and activities. Big resort!

Reviewed on Apr 22, 2025

Find the Best Chester Vacation Packages

Chester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Pittsburgh Intl. Airport (PIT)
Population
2,500
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Mountaineer Casino and The Mountaineer Race Track & Gaming Resort

Ready to book your vacation to Chester?

 

Choose your dates

Chester Hotel Deals

Welcome to the Auburn!
Welcome to the Auburn!
2 out of 5
Chester
The price is $189 per night from May 5 to May 6
$189
includes taxes & fees
$170 per night
May 5 - May 6
Fabulous
"Quiet. Perfect. Just what we needed"

Reviewed on Mar 23, 2025

Welcome to the Auburn!
La Quinta Inn by Wyndham Pittsburgh Airport
La Quinta Inn by Wyndham Pittsburgh Airport
2.5 out of 5
8507 University Blvd, Coraopolis, PA
Fully refundableReserve now, pay when you stay
The price is $89 per night from May 11 to May 12
$89
includes taxes & fees
$78 per night
May 11 - May 12
7.8/10 Good! (1,903 reviews)
"Staff was very friendly and transportation to/from airport was very good. Nothing bad about this stay comes to mind. Everything went well."

Reviewed on Apr 29, 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 $88 per night from May 4 to May 5
$88
includes taxes & fees
$77 per night
May 4 - May 5
6.6/10 (1,001 reviews)
"Done"

Reviewed on Apr 28, 2025

Wyndham Garden Pittsburgh Airport
See all 127 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 Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Chester vacation package cost?
You can grab a vacation package to this top destination from $358 on Expedia. However, how much your vacation 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?
If you’re looking to book a cheap Chester vacation package, consider planning a trip in September, October and November. You’re likely to find better rates on accommodations and flights during these months — perfect for a budget-friendly break.
How many days is enough for Chester?
With a well-organized schedule, you can easily hit the most popular Chester attractions in a few days. But if you want to explore off the beaten track or go on day trips, consider booking your Chester vacation for longer.
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 vacation package well in advance.
Is it cheaper to book a Chester vacation as a package?
Expedia vacation 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 personalized Chester vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation 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.
Does Expedia offer Book Now, Pay Later Chester vacation packages?
Jet off on your dream trip to Chester with our Book Now, Pay Later vacations. There’s no need to scrimp and save or wait until payday — we’ve partnered with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans let you split the cost over 3, 6 or 12 months. With no hidden or late payment fees, it’s a breeze to stay on budget and snag great deals while they last.

Discover the most popular places to visit in Chester

The Mountaineer Race Track & Gaming Resort

4/5(56 reviews)

Why not try your luck with a visit to The Mountaineer Race Track & Gaming Resort during your time in Chester? Take some time to visit the casinos in this family-friendly area.

The Mountaineer Race Track & Gaming Resort

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.