Chester Vacations from $707
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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.
Hampton Inn & Suites Pittsburgh-Downtown
Downtown Pittsburgh
Price was $1,100, price is now $963 per person
$963
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Pittsburgh (PIT)
9.4/10 Exceptional! (1,366 reviews)
The staff, on the whole, were lovely
Reviewed on Nov 12, 2026
Traveler's Rest Hotel
South Side Flats
Price was $1,455, price is now $1,300 per person
$1,300
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip flight included
Los Angeles (QLA) to Pittsburgh (PIT)
9.6/10 Exceptional! (129 reviews)
Private but not attached bathroom/ shower wad different, but very clean and roomy.
Reviewed on Nov 8, 2026
Stay near popular Chester attractions
Chester Hotel Deals
The Auburn Home - LPM
Chester WV
9.6/10 Exceptional! (15 reviews)
"Very clean and pretty"
Reviewed on Nov 3, 2026
Secluded Wilderness & Spa On Historic 2k Acre Wild Life Area
Chester WV
10/10 Exceptional! (1 review)
"The host has a quick response and everything you need is at the cabin! Property is beautiful with tons of trails to walk and very pet friendly. Everything was clean, organized, and the welcome gift and wine was a plus! Hot tub is very clean, secluded, and peaceful. If you’re thinking about booking, ..."
Reviewed on Oct 26, 2026
La Quinta Inn by Wyndham Pittsburgh Airport
8507 University Blvd Coraopolis PA
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $91 total per night from Nov 18 to Nov 19
$91 total
Nov 18 - Nov 19
Total with taxes and fees
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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- Visit Chester
- Mountaineer Casino Resort
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- Mountaineer Casino
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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.