Chester Vacations from $348

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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.
DoubleTree by Hilton Pittsburgh - Green Tree

DoubleTree by Hilton Pittsburgh - Green Tree

4 out of 5
per person
Nov 2 - Nov 7
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)
7.8/10 Good! (1,000 reviews)
Great location and nice staff.

Reviewed on Aug 13, 2025

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
Save 100% on your flight
per person
Nov 2 - Nov 7
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)
8/10 Very Good! (2,979 reviews)
Make the bed sheets cleaner. Ours had stains on them.

Reviewed on Aug 15, 2025

Hotel Indigo Pittsburgh East Liberty by IHG

Hotel Indigo Pittsburgh East Liberty by IHG

3.5 out of 5
East Liberty
Save 100% on your flight
per person
Sep 19 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)
8.2/10 Very Good! (1,006 reviews)
Great hotel, great area, but could’ve been cleaner. Shower ceiling also had peeling paint. Hotel staff and valet was very friendly.

Reviewed on Aug 15, 2025

Omni William Penn Hotel

Omni William Penn Hotel

4 out of 5
Downtown Pittsburgh
Save 100% on your flight
per person
Nov 2 - Nov 7
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)
9/10 Wonderful! (1,582 reviews)
Nice and great staff. Good location

Reviewed on Aug 13, 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
Nov 2 - Nov 7
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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 Aug 11, 2025

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Discover the most popular places to visit in Chester

The Mountaineer Race Track & Gaming Resort

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

Chester Hotel Deals

The Piedmont Cabin - LPM

The Piedmont Cabin - LPM

2 out of 5
Chester
$181 nightly
The price is $200 total per night from Aug 17 to Aug 18
$200 total
Aug 17 - Aug 18
Total includes taxes and fees
The Piedmont Cabin - LPM
The Auburn Home - LPM

The Auburn Home - LPM

2 out of 5
Chester
$235 nightly
The price is $257 total per night from Aug 17 to Aug 18
$257 total
Aug 17 - Aug 18
Total includes taxes and fees
10/10 Exceptional! (8 reviews)
"Clean, spacious, as advertised"

Reviewed on Jul 23, 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
$76 nightly
The price is $86 total per night from Aug 31 to Sep 1
$86 total
Aug 31 - Sep 1
Total includes taxes and fees
7.8/10 Good! (2,016 reviews)
"Great location."

Reviewed on Aug 12, 2025

La Quinta Inn by Wyndham Pittsburgh Airport
See all 133 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.

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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 $348 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.