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.
Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
Price was CA $1,054, price is now CA $792 per person
CA $792
per person
Nov 10 - Nov 14
found 17 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8.4/10 Very Good! (1,333 reviews)
My room had a mildewy smell, and wasn’t properly cleaned.

Reviewed on Aug. 22, 2025

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was CA $2,180, price is now CA $1,561 per person
CA $1,561
per person
Oct 11 - Oct 14
found 23 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Pittsburgh (PIT)
7.6/10 Good! (16 reviews)
Highly recommend! The property was great - with the stunning lobby, fast elevators, and clean, bright unit. Check was not required (after completing the online process & getting my code). The fully furnished apartment with lots of kitchen appliances & coffee! Bed was firm & comfortable, shower was hot with lots of pressure. It even had a washer/dryer. Great location - near restaurants & it really felt like it was connected to the city. Everyone (desk clerk, valet & manager) was friendly & helpful. Finding the parking was a challenge - I suggest calling ahead for directions to the garage.

Reviewed on Aug. 23, 2025

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Price was CA $1,722, price is now CA $1,291 per person
CA $1,291
per person
Oct 11 - Oct 14
found 23 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Pittsburgh (PIT)
8.6/10 Excellent! (1,001 reviews)
The property was great the and the sfaff were awesome.

Reviewed on Aug. 17, 2025

Kimpton Hotel Monaco Pittsburgh by IHG

Kimpton Hotel Monaco Pittsburgh by IHG

4.5 out of 5
Downtown Pittsburgh
Price was CA $1,147, price is now CA $861 per person
CA $861
per person
Nov 10 - Nov 13
found 20 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
9.4/10 Exceptional! (1,212 reviews)
One of my favorites! Always clean and comfortable Great bar/restaurant.

Reviewed on Aug. 24, 2025

Fairmont Pittsburgh

Fairmont Pittsburgh

4.5 out of 5
Downtown Pittsburgh
Price was CA $1,181, price is now CA $908 per person
CA $908
per person
Nov 10 - Nov 13
found 20 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8.8/10 Excellent! (1,000 reviews)
Everything was great

Reviewed on Aug. 12, 2025

Ready to book your vacation to Chester?

 

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Chester Hotel Deals

The Piedmont Cabin - LPM

The Piedmont Cabin - LPM

2 out of 5
Chester
The price is CA $207 per night from Aug 26 to Aug 27
CA $207
CA $275 total
Aug 26 - Aug 27
includes taxes & fees
The Piedmont Cabin - LPM
The Auburn Home - LPM

The Auburn Home - LPM

2 out of 5
Chester
The price is CA $252 per night from Aug 27 to Aug 28
CA $252
CA $355 total
Aug 27 - Aug 28
includes taxes & fees
10/10 Exceptional! (8 reviews)
"Clean, spacious, as advertised"

Reviewed on Jul. 23, 2025

The Auburn Home - LPM
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 $110 per night from Aug 31 to Sep 1
CA $110
CA $126 total
Aug 31 - Sep 1
includes taxes & fees
7.8/10 Good! (2,029 reviews)
"Very good place for a quick one night stay on the way."

Reviewed on Aug. 22, 2025

La Quinta Inn by Wyndham Pittsburgh Airport
See all 135 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 $792 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.