Title: Chester Vacation Packages 2026 from $508 | Expedia.com [Chester Travel Guide](https://expedia.com/Chester.dx55634)[Hotels in Chester](https://expedia.com/Chester-Hotels.d55634.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.com/Chester-Vacation-Rentals.d55634.Travel-Guide-VacationRentals)[Flights to Chester](https://expedia.com/Cheap-Flights-To-Chester.d55634.Travel-Guide-Flights)[Car Rentals in Chester](https://expedia.com/Car-Rentals-In-Chester.d55634.Car-Rental-Guide) ![](https://images.trvl-media.com/place/55634/4f382586-01ef-4a49-a418-7d9c181425c4.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chester Vacations from $508 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## 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](https://www.expedia.com/Mountaineer-Casino-New-Cumberland.d6292652.Vacation-Attraction), [The Mountaineer Race Track & Gaming Resort](https://www.expedia.com/The-Mountaineer-Race-Track-Gaming-Resort-Chester.d553248621532660254.Vacation-Attraction) and [Tomlinson Run State Park](https://www.expedia.com/Tomlinson-Run-State-Park-West-Virginia.d6295167.Vacation-Attraction). 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. ![DoubleTree by Hilton Pittsburgh Airport](https://images.trvl-media.com/lodging/2000000/1370000/1364000/1363975/06914b18_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### DoubleTree by Hilton Pittsburgh Airport $508 per person May 26 - May 31 found 14 hours ago Roundtrip flight included Boston (BOS) to Pittsburgh (PIT) 8.6/10 Excellent! (1,006 reviews) Clean room and great airport shuttle service Reviewed on Mar 18, 2026 ![The Westin Pittsburgh, a Marriott Hotel](https://images.trvl-media.com/lodging/1000000/20000/14300/14295/17a40a56_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Westin Pittsburgh, a Marriott Hotel Downtown Pittsburgh $1,240 per person May 19 - May 23 found 11 hours ago Roundtrip flight included Los Angeles (LAX) to Pittsburgh (PIT) 8.6/10 Excellent! (1,001 reviews) Staff and amenities were great! We loved our room. However, it looks like there were some drinks left in the mini fridge from the patron before us. Other than this, we had a wonderful stay. Reviewed on Jan 10, 2026 ![Placemakr Downtown Pittsburgh at The Pennsylvanian](https://images.trvl-media.com/lodging/115000000/114320000/114312800/114312743/0729901f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Placemakr Downtown Pittsburgh at The Pennsylvanian Downtown Pittsburgh Save 100% on your flight $937 per person May 21 - May 25 found 20 hours ago Roundtrip flight included Boston (BOS) to Pittsburgh (PIT) 8.2/10 Very Good! (71 reviews) Best place I have stayed in Pittsburgh Reviewed on Mar 16, 2026 ![DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown](https://images.trvl-media.com/lodging/1000000/10000/6200/6149/9f3454ce_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown Downtown Pittsburgh Save 100% on your flight $935 per person May 4 - May 8 found 1 day ago Roundtrip non-stop flight included Los Angeles (LAX) to Pittsburgh (PIT) 8.2/10 Very Good! (1,069 reviews) There was a finger nail on the carpet on our room (ewwww) and they ran out of cookies! Parking is non-existent at this location other than valet. Outside of that, staff was friendly. Would stay again Reviewed on Mar 16, 2026 ![Omni William Penn Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2998/7eb3a999_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Omni William Penn Hotel Downtown Pittsburgh Save 100% on your flight $782 per person May 21 - May 25 found 20 hours ago Roundtrip flight included Boston (BOS) to Pittsburgh (PIT) 9.2/10 Wonderful! (1,967 reviews) Excellent stay in downtown. Parking is very close to the building also. Near many great restaurants as well Reviewed on Mar 15, 2026 Don't see what you're looking for? See all available trips from Columbus to Chester [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-19/2026-04-26/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=PIT&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ### 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. [](https://expedia.com/Mountaineer-Casino-Resort-Chester.d553248621532660254.Vacation-Attraction) ## Chester Hotel Deals ![The Piedmont Cabin - LPM](https://images.trvl-media.com/lodging/107000000/106140000/106134400/106134341/2b4adca5_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Piedmont Cabin - LPM Chester WV $158 nightly $176 total Mar 20 - Mar 21 Total with taxes and fees 10/10 Exceptional! (3 reviews) Perfect place! Reviewed on Nov 30, 2025 [](https://expedia.com/Hotel-Search?startDate=3%2F20%2F2026&endDate=3%2F21%2F2026&selected=106134341&PinnedHotelID=106134341&HadPinnedHotel=true®ionId=55634) ![Hyatt Regency Pittsburgh International Airport](https://images.trvl-media.com/lodging/1000000/470000/464100/464013/34b3bae6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hyatt Regency Pittsburgh International Airport 710 Aviation Avenue Pittsburgh PA Fully refundableReserve now, pay when you stay $162 nightly $185 total Apr 4 - Apr 5 Total with taxes and fees 9.2/10 Wonderful! (1,597 reviews) Johannah at the front desk and Luann at breakfast made our stay! Had a flight cancellation and had to stay an extra night, rooms were clean and the hotel was quiet. Reviewed on Mar 19, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F4%2F2026&endDate=4%2F5%2F2026&selected=464013&PinnedHotelID=464013&HadPinnedHotel=true®ionId=55634) ![La Quinta Inn by Wyndham Pittsburgh Airport](https://images.trvl-media.com/lodging/1000000/10000/2500/2472/688276da_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### La Quinta Inn by Wyndham Pittsburgh Airport 8507 University Blvd Coraopolis PA Fully refundableReserve now, pay when you stay $71 nightly $81 total Mar 29 - Mar 30 Total with taxes and fees 8/10 Very Good! (2,235 reviews) The room was neat and clean and smelled of disinfectant. The bathroom clean with a facelift. Breakfast ok. Staff okay. They were conversing with each other in their native language as they checked us in which is rude and unprofessional and made me uncomfortable. Reviewed on Mar 17, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=2472&PinnedHotelID=2472&HadPinnedHotel=true®ionId=55634) [See all 153 properties in Chester](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F20%2F2026&endDate=3%2F21%2F2026®ionId=55634) 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](https://www.expedia.com/Mountaineer-Casino-New-Cumberland.d6292652.Vacation-Attraction) and [The Mountaineer Race Track & Gaming Resort](https://www.expedia.com/The-Mountaineer-Race-Track-Gaming-Resort-Chester.d553248621532660254.Vacation-Attraction) | ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) 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Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Honeymoon Vacations [](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Mountain Vacations [](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does a Chester vacation package cost? ### What are the cheapest months to go to Chester? ### How many days is enough for Chester? ### How to find the best Chester package deals? ### Is it cheaper to book a Chester vacation as a package? ### When to book a vacation package to Chester? ### Does Expedia offer Book Now, Pay Later Chester vacation packages? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Mountaineer Casino Resort ](https://www.expedia.com/The-Mountaineer-Race-Track-Gaming-Resort-Hotels.0-l553248621532660254-0.Travel-Guide-Filter-Hotels) - [Newell Hotels ](https://www.expedia.com/Newell-Hotels.d6047380.Travel-Guide-Hotels) - [Romantic Hotels in Newell ](https://www.expedia.com/Newell-Hotels-Romantic-Hotel.0-0-d6047380-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Casino Hotels in Newell ](https://www.expedia.com/Newell-Hotels-Casino-Hotel.0-0-d6047380-tCasinoHotel.Travel-Guide-Filter-Hotels) - [B&B in Newell ](https://www.expedia.com/Newell-Bed-And-Breakfast.d6047380-aaBedAndBreakfast.Travel-Guide-Accommodation) - [5 Star Hotels in Newell 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