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.
Hotel Indigo Pittsburgh East Liberty by IHG

Hotel Indigo Pittsburgh East Liberty by IHG

3.5 out of 5
East Liberty
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Pittsburgh (PIT)
8.2/10 Very Good! (1,010 reviews)
Good area in east liberty

Reviewed on Jul. 9, 2025

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Pittsburgh (PIT)
8/10 Very Good! (2,897 reviews)
The hotel was nice and clean and a short walking distance to the park and baseball stadium.

Reviewed on Jul. 8, 2025

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Pittsburgh (PIT)
8.2/10 Very Good! (1,303 reviews)
Very friendly and kind front desk staff. The room is beautiful, clean and comfortable! Top notch. I highly recommend this property.

Reviewed on Jul. 5, 2025

Placemakr Downtown Pittsburgh

Placemakr Downtown Pittsburgh

4 out of 5
Downtown Pittsburgh
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Pittsburgh (PIT)
9.4/10 Exceptional! (6 reviews)
It was a difficult time getting in to park - there were no clear instructions, and their main portico was blocked off for a wedding the next day. We were let in by Valet, who wasn't supposed to let us get in until we had a code, but we couldn't park anywhere to get in to get said code. Once inside, the onsite person was friendly, but clueless. We actually had to help him check us in. A little embarrassing, but we got in. The unit was very clean! The space was perfect for our stay.

Reviewed on Jul. 7, 2025

Fairfield Inn & Suites by Marriott Pittsburgh Downtown

Fairfield Inn & Suites by Marriott Pittsburgh Downtown

2.5 out of 5
Downtown Pittsburgh
per person
Sep 12 - Sep 16
found 21 hours ago
Roundtrip flight included
Spokane (GEG) to Pittsburgh (PIT)
8.8/10 Excellent! (766 reviews)
Panhandling and homeless people in areas outside of building. We were nervous about walking around and saw several homeless camps by the river area.

Reviewed on Jul. 8, 2025

Ready to book your vacation to Chester?

 

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Chester Hotel Deals

La Quinta Inn by Wyndham Pittsburgh Airport
La Quinta Inn by Wyndham Pittsburgh Airport
3 out of 5
8507 University Blvd, Coraopolis, PA
Fully refundableReserve now, pay when you stay
The price is CA $116 per night from Jul 27 to Jul 28
CA $116
CA $132 total
Jul 27 - Jul 28
includes taxes & fees
7.8/10 Good! (1,987 reviews)
"Everyone was fantastic"

Reviewed on Jul. 6, 2025

La Quinta Inn by Wyndham Pittsburgh Airport
Hyatt Regency Pittsburgh International Airport
Hyatt Regency Pittsburgh International Airport
3.5 out of 5
710 Aviation Avenue, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is CA $286 per night from Jul 20 to Jul 21
CA $286
CA $326 total
Jul 20 - Jul 21
includes taxes & fees
9/10 Wonderful! (1,492 reviews)
"On-site at airport. Clean comfortable room. Hotel bar with good snacks"

Reviewed on Jul. 5, 2025

Hyatt Regency Pittsburgh International Airport
Sleep Inn & Suites Pittsburgh
Sleep Inn & Suites Pittsburgh
2.5 out of 5
1000 Park Lane Drive Sleep Inn Bldg B, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is CA $103 per night from Jul 13 to Jul 14
CA $103
CA $118 total
Jul 13 - Jul 14
includes taxes & fees
8/10 Very Good! (1,008 reviews)
"The room had a small partition the separated the living rooms from the sleeping area."

Reviewed on Jul. 7, 2025

Sleep Inn & Suites Pittsburgh
See all 130 properties in Chester
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Chester vacation package cost?
You can grab a vacation package to this top destination from CA $747 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?

  1. Choose your travel dates: The things you'd like to do in Chester and your favourite season will help you decide when to go.
  2. 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.
  3. 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.
  4. 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.