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.
Red Roof Inn PLUS+ Pittsburgh East - Monroeville
Price was CA $1,054, price is now CA $801 per person
CA $801
per person
Apr 22 - Apr 25
found 9 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Pittsburgh (PIT)
6/10 (1,007 reviews)
somewhat-- make sure there is toilet paper in the room
Reviewed on Feb 9, 2026
The Westin Pittsburgh, a Marriott Hotel
Downtown Pittsburgh
Price was CA $1,982, price is now CA $1,466 per person
CA $1,466
per person
May 15 - May 18
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Pittsburgh (PIT)
8.6/10 Excellent! (1,003 reviews)
Staff and amenities were great! We loved our room. However, it looks like there were some drinks left in the mini fridge from the patron before us. Other than this, we had a wonderful stay.
Reviewed on Jan 10, 2026
Placemakr Downtown Pittsburgh at The Pennsylvanian
Downtown Pittsburgh
Price was CA $2,366, price is now CA $1,783 per person
CA $1,783
per person
Apr 22 - Apr 25
found 9 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Pittsburgh (PIT)
7.6/10 Good! (37 reviews)
Very friendly staff and clean room.
Reviewed on Feb 1, 2026
Etage Executive Living
Downtown Pittsburgh
Price was CA $2,445, price is now CA $1,864 per person
CA $1,864
per person
Apr 22 - Apr 25
found 9 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Pittsburgh (PIT)
9.2/10 Wonderful! (1,483 reviews)
Room was clean, had good amenities, felt safe, was very accessible and close to things. The check in/check out process was easy. If you're next to/below loud people you will hear them, fairly thin walls and floors but wasnt a huge issue after 10pm.
Reviewed on Feb 22, 2026
Chester Hotel Deals
The Piedmont Cabin - LPM
Chester WV
The price is CA $189 per night from Mar 2 to Mar 3
CA $189
CA $240 total
Mar 2 - Mar 3
includes taxes & fees
10/10 Exceptional! (3 reviews)
Perfect place!
Reviewed on Nov 30, 2025
Hyatt Regency Pittsburgh International Airport
710 Aviation Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is CA $212 per night from Mar 15 to Mar 16
CA $212
CA $242 total
Mar 15 - Mar 16
includes taxes & fees
9/10 Wonderful! (1,594 reviews)
Great easy hotel for quick access to airport
Reviewed on Feb 25, 2026
La Quinta Inn by Wyndham Pittsburgh Airport
8507 University Blvd Coraopolis PA
Fully refundableReserve now, pay when you stay
The price is CA $97 per night from Mar 1 to Mar 2
CA $97
CA $111 total
Mar 1 - Mar 2
includes taxes & fees
8/10 Very Good! (2,225 reviews)
Deluxe room is not. No gaming system as advertised in the listing. Fridge and microwave were connected to the same light switch that turned on the lights for the room. So lights off, they are off. Sketchy, dark parking area. Back doors are not secured overnight. Anyone could have entered that hotel ...
Reviewed on Feb 24, 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.
