Chester Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Stay Pittsburgh
Downtown Pittsburgh
CA $1,275
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Saskatoon (YXE) to Pittsburgh (PIT)
8/10 Very good! (325 reviews)
The property was located in a good area for what we where there for. The staff was friendly and made sure we were taken care of. Our check-in time was 3pm we arrived around 4pm. Upon entering the property it was clean and smelled amazing. Once we made it to our room it wasn't clean the bedding was still on from the previous guest, microwave was dirty as well as the floor had a sticky substance on it which means it hadn't been mopped, the TV in the bedroom did not work. We called the property immediately left a message and they called us right back. They apologized and had a young man who spoke no English (which made it hard to communicate) he apologized again and finished cleaning the apartment and changed the bedding. Once he finished the property called back and offered a discount which we still haven't received. I will suggest that the owners of this property do a deep clean. A fresh coat of paint or even wiping the walls down would work as well as changing the shower curtains. I don't think we will come back here.
Reviewed on Sep 24, 2026
The Westin Pittsburgh, a Marriott Hotel
Downtown Pittsburgh
CA $1,490
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Saskatoon (YXE) to Pittsburgh (PIT)
8.6/10 Excellent! (1,004 reviews)
I would highly recommend! We spent our 2nd anniversary there for the Steelers game and when we arrived to our room they were so kind to leave us some goodies and a little note to congratulate us! It was a very clean hotel and room! Staffing very kind! Will be staying again for sure!
Reviewed on Sep 14, 2026
The Inn on Negley
Shadyside
CA $1,383
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Saskatoon (YXE) to Pittsburgh (PIT)
10/10 Exceptional! (224 reviews)
So clean! A beautiful house and an amazing breakfast! Staff were wonderful. Short walk to shops and restaurants. Highly recommended.
Reviewed on Sep 23, 2026
Joinery Hotel Pittsburgh, Curio Collection by Hilton
Downtown Pittsburgh
CA $1,344
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Saskatoon (YXE) to Pittsburgh (PIT)
8.6/10 Excellent! (1,659 reviews)
Todo queda a distancia de 15 minutos a pie. Fueron tres habitaciones y en una de ellas las toallas eran de microfibra lo que no nos agradó. Preferiría las de algodón. Pero quitando ese detalle insignificante fue un excelente destino que lo recomiendo 100%.
Reviewed on Sep 26, 2026
Ready to book your vacation to Chester?
Chester Hotel Deals
The Piedmont Cabin 2 bed, 1.5 bath
Chester WV
10/10 Exceptional! (10 reviews)
"Beautiful location, beautiful house, beautiful property. Great weekend close to everything."
Reviewed on Sep 19, 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.
Stay near popular Chester attractions
Pleasant Hills Golf Course
Enjoy a round of golf in Chester at Pleasant Hills Golf Course. Amble around the area's riverfront or visit its casinos.
Tomlinson Run Lake
Commune with nature and explore the great outdoors at Tomlinson Run Lake during your travels in Chester. Amble around the area's riverfront or visit its casinos.
Frequently asked questions
How much does a Chester vacation package cost?
You can grab a vacation package to this top destination from CA $1,234 on Expedia. But how much your vacation to Chester costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Chester?
The off-season is the best time to travel to Chester if you're on a budget. Another tip for getting cheap Chester vacation packages? Avoid visiting during public holidays and any major events or festivals.
How many days is enough for Chester?
The ideal duration for your Chester vacation depends on what you'd like to see. Generally, a handful of days to a week will give you time to tick off all the main attractions and discover some hidden spots along the way.
How to find the best Chester package deals?
Use Expedia's filters to help you find some of the best Chester package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Chester package deals in the off-peak season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Chester vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll typically score a better deal than booking each component separately. And you'll still get the freedom to create a customized Chester vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Chester?
If you're planning a spur-of-the-moment Chester getaway, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find amazing deals on your flights and hotels by booking well in advance.
How to plan a trip to Chester?
- Choose your travel dates: The things you'd like to do in Chester and your favourite season will help you decide when to go.
- Figure out your budget: Ensure you have enough money to pay for everything from food and transportation to activities and airfares. Your accommodations will probably be the largest expense during your trip to Chester.
- Decide how long to go for: Now that you're up to speed on Chester, you can figure out the ideal length of your break. Create a draft itinerary and give yourself enough time to cover everything you want to see.
- Combine your airfare and accommodations: After you've settled on your trip dates and duration, book the right Chester vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
