Chester Vacations from $265

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Photo by Bill Dillard

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.
Hotel Indigo Pittsburgh East Liberty by IHG

Hotel Indigo Pittsburgh East Liberty by IHG

3.5 out of 5
East Liberty
per person
Sep 14 - Sep 16
found 4 hours ago
Roundtrip non-stop flight included
Nashville (BNA) to Pittsburgh (PIT)
8.2/10 Very Good! (1,010 reviews)
Front desk staffs were excellent and quick check in and check out. Room was good size and very clean. Breakfast was not that great. Parking is available per Expedia portal so I misunderstood it will be a free self parking but valet parking only. Very expensive. OK, to stay if you dont want to pay too much for one night.

Reviewed on Jun 28, 2025

Seven Springs Resort Properties

Seven Springs Resort Properties

4 out of 5
Save 100% on your flight
per person
Sep 11 - Sep 15
found 18 hours ago
Roundtrip flight included
Orlando (MCO) to Pittsburgh (PIT)
8/10 Very Good! (12 reviews)
The condo was perfect for our family. 3 bedrooms, 3 bathrooms and a kitchen with plenty of pots/pans/utensils to cook your own meals. Its a great place to get away with the family in nature, play board games and just spend time together.

Reviewed on Jun 28, 2025

Slopeside Hotel by Seven Springs Resort

Slopeside Hotel by Seven Springs Resort

4.5 out of 5
Save 100% on your flight
per person
Sep 11 - Sep 15
found 18 hours ago
Roundtrip flight included
Orlando (MCO) to Pittsburgh (PIT)
8.8/10 Excellent! (286 reviews)
There were several dining options on property.

Reviewed on Jun 21, 2025

Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
Save 100% on your flight
per person
Sep 12 - Sep 15
found 3 hours ago
Roundtrip flight included
Orlando (MCO) to Pittsburgh (PIT)
7.6/10 Good! (142 reviews)
The view and size was great great concept. For downtown

Reviewed on Jun 29, 2025

Omni William Penn Hotel

Omni William Penn Hotel

4 out of 5
Downtown Pittsburgh
per person
Sep 14 - Sep 16
found 4 hours ago
Roundtrip non-stop flight included
Nashville (BNA) to Pittsburgh (PIT)
9/10 Wonderful! (1,503 reviews)
Property was great love the old hotel feeling. It was convenient to everything we wanted do. Enjoyed the SpeakEasy as well. The only complaint is on Saturday night at 9:30 the Speakeasy was ALL OUT OF their LIGHT FARE FOOD. They are only open 3 nights a week this should never Happen.

Reviewed on Jun 29, 2025

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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

Chester Hotel Deals

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
$84 nightly
The price is $96 total per night from Jul 7 to Jul 8
$96 total
Jul 7 - Jul 8
Total includes taxes and fees
7.8/10 Good! (1,969 reviews)
"Everything was as advertised"

Reviewed on Jun 26, 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
$88 nightly
The price is $101 total per night from Jul 3 to Jul 4
$101 total
Jul 3 - Jul 4
Total includes taxes and fees
6.6/10 (1,001 reviews)
"The people at the front desk were friendly the breakfast that they offered was very lacking but aside from that everything else was great."

Reviewed on Jun 27, 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
$199 nightly
The price is $227 total per night from Jul 4 to Jul 5
$227 total
Jul 4 - Jul 5
Total includes taxes and fees
9/10 Wonderful! (1,480 reviews)
"Convenient to airport"

Reviewed on Jun 27, 2025

Hyatt Regency Pittsburgh International 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.

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 $265 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.