Chester Vacations from $401
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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
Downtown Pittsburgh
$477
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
8.2/10 Very Good! (3,705 reviews)
The hotel was nice and in a good location to visit PNC park. The only issue we ran into was our room was not ready and we had to wait over an hour.
Reviewed on Aug 21, 2026
Fairmont Pittsburgh
Downtown Pittsburgh
$1,606
per person
Oct 3 - Oct 10
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
8.8/10 Excellent! (1,002 reviews)
Rooms were clean, staff were excellent. Restaurant was not as clean as rooms
Reviewed on Aug 6, 2026
Stay near popular Chester attractions
Mountaineer Casino Resort
7.8/10 (118 reviews)
This all-in-one entertainment venue combines thrilling casino gaming with live thoroughbred racing in West Virginia. Enhance your visit with a round on the championship golf course or rejuvenate at the full-service spa.
Tomlinson Run Lake
This 30-acre lake offers serene fishing for bass, catfish, and trout within West Virginia's rolling hills. Rent kayaks or paddleboats during summer months to explore its peaceful waters surrounded by lush greenery.
Pleasant Hills Golf Course
This traditional 9-hole course offers a scenic backdrop for golfers of all skill levels since 1961. Enjoy the driving range and complete your relaxed round in about two hours during pleasant spring or fall mornings.
Chester Hotel Deals
The Piedmont Cabin 2 bed, 1.5 bath
Chester WV
10/10 Exceptional! (9 reviews)
"We had a great 3 night stay here. The cabin is absolutely adorable and the host has thought of every possible detail to make your visit feel just like home! Everything was very nice and clean. Communication with the host was excellent from the moment of booking, to the day of departure. It is tucked ..."
Reviewed on Aug 18, 2026
The Auburn Home - LPM
Chester WV
9.6/10 Exceptional! (14 reviews)
"Wonderful place to stay!!!! Definitely will stay again if we make it back that way ."
Reviewed on Aug 6, 2026
Secluded Wilderness & Spa On Historic 2k Acre Wild Life Area
Chester WV
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 $401 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.
