Chester Vacations from $285

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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.
Hampton Inn Pittsburgh/West Mifflin

Hampton Inn Pittsburgh/West Mifflin

2.5 out of 5
Price was $423, price is now $285 per person
$285
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
17.2/10 Exceptional! (737 reviews)
Stayed here on two separate occasions during a visit to the area. On both occasions the rooms were to the usual standard expected from a Hampton and the large TV provided crisp images. The lady on the front desk recognised us from our first stay.

Reviewed on Nov 13, 2025

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $505, price is now $311 per person
$311
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
16.4/10 Exceptional! (3,142 reviews)
The pillows are way too small. For the cost per night, I expected better.

Reviewed on Nov 18, 2025

Hotel Indigo Pittsburgh East Liberty by IHG

Hotel Indigo Pittsburgh East Liberty by IHG

3.5 out of 5
East Liberty
Price was $468, price is now $297 per person
$297
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
16/10 Exceptional! (1,003 reviews)
Their breakfast deal was a wonderful meal at their in house restaurant.

Reviewed on Nov 7, 2025

Kimpton Hotel Monaco Pittsburgh by IHG

Kimpton Hotel Monaco Pittsburgh by IHG

4.5 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $739, price is now $495 per person
$495
per person
Jan 11 - Jan 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
18.8/10 Exceptional! (1,253 reviews)
The room was amazing and the staff was wonderful!

Reviewed on Nov 13, 2025

Renaissance Pittsburgh Hotel

Renaissance Pittsburgh Hotel

4 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $696, price is now $478 per person
$478
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
18/10 Exceptional! (1,001 reviews)
The hotel is nice but most of the rooms have very bad views. You are looking at parking garages or other rooms. It's in a great location if you are going to a Pirates game.

Reviewed on Nov 12, 2025

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Discover the most popular places to visit in Chester

Mountaineer Casino Resort

4/5(56 reviews)

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

Mountaineer Casino Resort

Chester Hotel Deals

The Piedmont Cabin - LPM

The Piedmont Cabin - LPM

2 out of 5
Chester WV
$158 nightly
The price is $176 total per night from Nov 30 to Dec 1
$176 total
Nov 30 - Dec 1
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
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
$189 nightly
The price is $215 total per night from Dec 5 to Dec 6
$215 total
Dec 5 - Dec 6
Total with taxes and fees
9/10 Wonderful! (1,588 reviews)
Yes

Reviewed on Nov 14, 2025

Hyatt Regency Pittsburgh International Airport
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
$73 nightly
The price is $83 total per night from Nov 23 to Nov 24
$83 total
Nov 23 - Nov 24
Total with taxes and fees
8/10 Very Good! (2,118 reviews)
Great place to stay and very safe and friendly environment

Reviewed on Nov 15, 2025

La Quinta Inn by Wyndham Pittsburgh Airport
See all 140 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 $285 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.