Chester Vacations from $326

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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.
Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $615, price is now $326 per person
$326
per person
Apr 17 - Apr 19
found 18 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Pittsburgh (PIT)
8.2/10 Very Good! (3,142 reviews)
The room was very clean and all the staff was top notch for service. The valet parking was nothing more than organized chaos. There was a dance event at the hotel so that added to the loads of cars stacking up in front, but I guess if that’s all I have to point out then it wasn’t that bad. We’ll definitely be back, highly recommend.

Reviewed on Feb 1, 2026

City Sights 2 Queen Beds Downtown Apt

City Sights 2 Queen Beds Downtown Apt

2 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $3,999, price is now $3,190 per person
$3,190
per person
Apr 22 - Apr 26
found 9 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Pittsburgh (PIT)
6/10 (1 review)
2 Bedroom 2 Bath City Views

2 Bedroom 2 Bath City Views

2 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $3,969, price is now $3,166 per person
$3,166
per person
Apr 22 - Apr 26
found 9 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Pittsburgh (PIT)
No reviews
The Colonial Mt. Lebanon by Luxe PGH

The Colonial Mt. Lebanon by Luxe PGH

3 out of 5
Mount Lebanon
Price was $997, price is now $796 per person
$796
per person
Apr 22 - Apr 26
found 9 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Pittsburgh (PIT)
2/10 (2 reviews)
2 Bedroom Downtown Apt City Views Park Walk

2 Bedroom Downtown Apt City Views Park Walk

2 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $3,860, price is now $3,081 per person
$3,081
per person
Apr 22 - Apr 26
found 9 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Pittsburgh (PIT)
No reviews
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Discover the most popular places to visit in Chester

Mountaineer Casino Resort

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

Mountaineer Casino Resort

Chester Hotel Deals

The Piedmont Cabin - LPM

The Piedmont Cabin - LPM

2 out of 5
Chester WV
$158 nightly
The price is $176 total per night from Mar 1 to Mar 2
$176 total
Mar 1 - Mar 2
Total with taxes and fees
10/10 Exceptional! (3 reviews)
Perfect place!

Reviewed on Nov 30, 2025

The Piedmont Cabin - LPM
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
$149 nightly
The price is $170 total per night from Feb 7 to Feb 8
$170 total
Feb 7 - Feb 8
Total with taxes and fees
9/10 Wonderful! (1,610 reviews)
Staff was friendly. Room was clean.

Reviewed on Jan 27, 2026

Hyatt Regency Pittsburgh International Airport
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
$62 nightly
The price is $70 total per night from Feb 22 to Feb 23
$70 total
Feb 22 - Feb 23
Total with taxes and fees
8/10 Very Good! (2,223 reviews)
Room was outdated but it looks like the hotel will be updated/renovated soon

Reviewed on Jan 30, 2026

La Quinta Inn by Wyndham Pittsburgh Airport
See all 151 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.

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

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Frequently asked questions

How much does a Chester vacation package cost?
You can grab a vacation package to this top destination from $326 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.

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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.