Chester Vacations from $370

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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.

The Latest Chester vacation packages

Price found within the past 48 hours. Click for updated prices.
Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
Price was $469, price is now $370 per person
$370
per person
Aug 16 - Aug 18
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)
8/10 Very Good! (298 reviews)
Affordable

Reviewed on Jul 4, 2026

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $1,358, price is now $981 per person
$981
per person
Aug 13 - Aug 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8.6/10 Excellent! (1,000 reviews)
It was just ok. Maybe Pittsburgh needs to get a Ritz or Four Seasons.

Reviewed on Jun 24, 2026

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was $1,046, price is now $808 per person
$808
per person
Aug 13 - Aug 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8.6/10 Excellent! (146 reviews)
Right near the bus terminal so it can get sketchy walking around. Loved the washer and dryer in the room. Heads up to bring unscented detergent if fragrances bother you.

Reviewed on Jul 2, 2026

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
Price was $946, price is now $742 per person
$742
per person
Aug 13 - Aug 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
8.6/10 Excellent! (1,543 reviews)
The bartender Russ was phenomenal. The service at the front desk was excellent.

Reviewed on Jul 3, 2026

DoubleTree by Hilton Pittsburgh - Green Tree

DoubleTree by Hilton Pittsburgh - Green Tree

4 out of 5
Price was $712, price is now $562 per person
$562
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
8.6/10 Excellent! (1,038 reviews)
Room looked clean but the base of the standing lamp behind the sofa was disgustfully filthy that questions about the rest, it does not look like it was cleaned for some time

Reviewed on Jul 3, 2026

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Stay near popular Chester attractions

Mountaineer Casino Resort

7.8/10 (118 reviews)
This all-in-one entertainment venue combines thrilling casino gaming with live thoroughbred racing in West Virginia. Enhance your visit with a round on the championship golf course or rejuvenate at the full-service spa.
See properties

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
$82 nightly
The price is $93 total per night from Jul 20 to Jul 21
$93 total
Jul 20 - Jul 21
Total with taxes and fees
8.2/10 Very Good! (2,331 reviews)
"The room felt very modern. Love that."

Reviewed on Jul 4, 2026

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
$169 nightly
The price is $193 total per night from Jul 12 to Jul 13
$193 total
Jul 12 - Jul 13
Total with taxes and fees
9.2/10 Wonderful! (1,694 reviews)
"Unable to change or refund stay for wrong night."

Reviewed on Jul 4, 2026

Hyatt Regency Pittsburgh International Airport
Sheraton Pittsburgh Airport Hotel

Sheraton Pittsburgh Airport Hotel

3.5 out of 5
1160 Thorn Run Rd Coraopolis PA
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $108 total per night from Jul 12 to Jul 13
$108 total
Jul 12 - Jul 13
Total with taxes and fees
8.6/10 Excellent! (1,001 reviews)
"Very close to airport and worth the money."

Reviewed on Jul 2, 2026

Sheraton Pittsburgh Airport Hotel
See all 172 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.

Find the Best Chester Vacation Packages

Chester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Pittsburgh Intl. Airport (PIT)
Population
2,500
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Mountaineer Casino and The Mountaineer Race Track & Gaming Resort

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Frequently asked questions

How much does a Chester vacation package cost?
You can grab a vacation package to this top destination from $370 on Expedia. However, how much your vacation to Chester costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Chester?
If you're looking to book a cheap Chester vacation package, consider planning a trip in September, October and November. You're likely to find better rates on accommodations and flights during these months — perfect for a budget-friendly break.
How many days is enough for Chester?
With a well-organized schedule, you can easily hit the most popular Chester attractions in a few days. But if you want to explore off the beaten track or go on day trips, consider booking your Chester vacation for longer.
How to find the best Chester package deals?
Use Expedia's filter tool to help you find some great Chester package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or search for Chester package deals in the off-peak season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book a Chester vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll usually snag a better deal than booking each component individually. And you'll still enjoy the freedom to create a personalized Chester vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Chester?
If you're planning a spontaneous Chester getaway, check out our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can find amazing deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Chester vacation packages?
Jet off on your dream trip to Chester with our Book Now, Pay Later vacations. There's no need to scrimp and save or wait until payday — we've partnered with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans let you split the cost over 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to stay on budget and snag great deals while they last.

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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.