Chester Vacations from $495

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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.
Hotel Indigo Pittsburgh East Liberty by IHG

Hotel Indigo Pittsburgh East Liberty by IHG

3.5 out of 5
East Liberty
Save 100% on your flight
Price was $744, price is now $495 per person
$495
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Pittsburgh (PIT)
8.2/10 Very Good! (1,012 reviews)
Homeless person came into the hotel lobby and sat in the lounge couch across from us, asking for money through PayPal. None of the hotel attendants in the lobby paid any attention, and let it happen. The room was partially cleaned. I've never been to a hotel where they partially cleaned a room. Very odd. The staffs abrasiveness can be less desirable. Probably won't be back to this location.

Reviewed on Sep 16, 2025

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 $1,333, price is now $902 per person
$902
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Pittsburgh (PIT)
8.6/10 Excellent! (1,002 reviews)
It's an excellent hotel in an excellent locale.

Reviewed on Sep 7, 2025

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $979, price is now $663 per person
$663
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Pittsburgh (PIT)
8.2/10 Very Good! (3,030 reviews)
Staff was friendly and place was clean and beds were super comfy. Transportation was close to everything as well!

Reviewed on Sep 16, 2025

Fairmont Pittsburgh

Fairmont Pittsburgh

4.5 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $1,834, price is now $1,269 per person
$1,269
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
8.8/10 Excellent! (1,004 reviews)
Very clean, great location

Reviewed on Sep 16, 2025

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $1,154, price is now $823 per person
$823
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Pittsburgh (PIT)
7.6/10 Good! (22 reviews)
The carpet has a very strong odor. Trash shoot is broken plus smells terrible, just have other people take it out after your stay. Was getting different messages from front desk staff. Ubers go aroud the corner and drop you off around the block because GPS takes you there.

Reviewed on Sep 15, 2025

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Discover the most popular places to visit in Chester

The Mountaineer Race Track & Gaming Resort

Why not try your luck with a visit to The Mountaineer Race Track & Gaming Resort during your time in Chester? Take some time to visit the casinos in this family-friendly area.

The Mountaineer Race Track & Gaming Resort

Chester Hotel Deals

The Piedmont Cabin - LPM

The Piedmont Cabin - LPM

2 out of 5
Chester
$135 nightly
The price is $150 total per night from Sep 22 to Sep 23
$150 total
Sep 22 - Sep 23
Total with taxes and fees
10/10 Exceptional! (1 review)
"Cozy and clean cabin. Very responsive host. Highly recommend."

Reviewed on Aug 30, 2025

The Piedmont Cabin - LPM
The Auburn Home - LPM

The Auburn Home - LPM

2 out of 5
Chester
$170 nightly
The price is $189 total per night from Sep 29 to Sep 30
$189 total
Sep 29 - Sep 30
Total with taxes and fees
9.6/10 Exceptional! (10 reviews)
"Clean, spacious, as advertised"

Reviewed on Jul 23, 2025

The Auburn Home - LPM
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
$201 nightly
The price is $229 total per night from Oct 18 to Oct 19
$229 total
Oct 18 - Oct 19
Total with taxes and fees
9/10 Wonderful! (1,538 reviews)
"I liked that I could walk directly to the airport."

Reviewed on Sep 14, 2025

Hyatt Regency Pittsburgh International Airport
See all 137 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.

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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 $495 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.