Chester Vacation Packages
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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.
Top Chester Vacation Deals
Price found within the past 48 hours. Click for updated prices.
TownePlace Suites by Marriott Pittsburgh Cranberry Township
Price was CA $977, price is now CA $758 per person
CA $758
per person
Jun 5 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Pittsburgh (PIT)
9.2/10 Wonderful! (435 reviews)
Great spot with full kitchen in room
Reviewed on Apr 5, 2026
Hilton Garden Inn Pittsburgh University Place
Central Oakland
Price was CA $1,580, price is now CA $1,252 per person
CA $1,252
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Pittsburgh (PIT)
8.8/10 Excellent! (1,006 reviews)
Clean, staff was very hospitable. Walking distance from university
Reviewed on Apr 12, 2026
Hyatt House Pittsburgh/Bloomfield/Shadyside
Bloomfield
Price was CA $1,680, price is now CA $1,368 per person
CA $1,368
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Pittsburgh (PIT)
9/10 Wonderful! (1,001 reviews)
The only unfortunate part is that the bar closes very early.
Reviewed on Apr 12, 2026
Chester Hotel Deals
The Piedmont Cabin 2 bed, 1.5 bath
Chester WV
10/10 Exceptional! (4 reviews)
Very nice cute little cottage. Nice and beautiful decorations. Very quiet!
Reviewed on Apr 6, 2026
The Auburn Home - LPM
Chester WV
9.6/10 Exceptional! (12 reviews)
House was clean and well maintained.
Reviewed on Apr 4, 2026
Hyatt Regency Pittsburgh International Airport
710 Aviation Avenue Pittsburgh PA
The price is CA $248 per night from Apr 19 to Apr 20
CA $248
CA $282 total
Apr 19 - Apr 20
includes taxes & fees
9/10 Wonderful! (1,644 reviews)
Expensive breakfast buffet at $20 so I didn't eat breakfast. Bar staff was very good.
Reviewed on Apr 13, 2026
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
