Title: Chester Vacation Packages & Trips 2026 from CA $800 | Expedia.ca [Hotels in Chester](https://expedia.ca/Chester-Hotels.d55634.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d55634.Travel-Guide-VacationRentals)[Chester Car Rentals](https://expedia.ca/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 Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 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.ca/Mountaineer-Casino-New-Cumberland.d6292652.Vacation-Attraction), [The Mountaineer Race Track & Gaming Resort](https://www.expedia.ca/The-Mountaineer-Race-Track-Gaming-Resort-Chester.d553248621532660254.Vacation-Attraction) and [Tomlinson Run State Park](https://www.expedia.ca/Tomlinson-Run-State-Park-West-Virginia.d6295167.Vacation-Attraction). 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. ![Stay Pittsburgh](https://images.trvl-media.com/lodging/78000000/77870000/77861900/77861820/7b586e0e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Stay Pittsburgh Downtown Pittsburgh CA $800 per person Apr 2 - Apr 6 found 1 day ago Roundtrip flight included Halifax (YHZ) to Pittsburgh (PIT) 7.8/10 Good! (203 reviews) Clean and very cozy Reviewed on Feb 1, 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 CA $1,293 per person Apr 2 - Apr 6 found 1 day ago Roundtrip flight included Halifax (YHZ) to Pittsburgh (PIT) 8.6/10 Excellent! (1,003 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 ![Ramada by Wyndham Butler/Tesla Biohealing Resort](https://images.trvl-media.com/lodging/84000000/83140000/83130900/83130847/fe34f7c8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ramada by Wyndham Butler/Tesla Biohealing Resort CA $1,206 per person Mar 15 - Mar 22 found 20 hours ago Roundtrip non-stop flight included Montreal (YMQ) to Pittsburgh (PIT) 7.8/10 Good! (109 reviews) Everything is brand new, awesome pillows and mattresses! Parking close to room. The FLOOR in my room was cold, my only negative. Reviewed on Feb 1, 2026 ![Hilton Garden Inn Pittsburgh Area Beaver Valley, PA](https://images.trvl-media.com/lodging/37000000/36270000/36261800/36261745/3812b330_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Garden Inn Pittsburgh Area Beaver Valley, PA CA $1,321 per person Mar 15 - Mar 22 found 20 hours ago Roundtrip non-stop flight included Montreal (YMQ) to Pittsburgh (PIT) 9/10 Wonderful! (371 reviews) Rverything was top tier! Reviewed on Feb 1, 2026 ![DoubleTree by Hilton Pittsburgh - Cranberry](https://images.trvl-media.com/lodging/1000000/10000/1200/1172/a953fc19_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### DoubleTree by Hilton Pittsburgh - Cranberry CA $1,466 per person Mar 15 - Mar 22 found 20 hours ago Roundtrip non-stop flight included Montreal (YMQ) to Pittsburgh (PIT) 8.8/10 Excellent! (913 reviews) Breakfast was delicious and the entire stay was great! The kids especially loved the indoor pool! Reviewed on Jan 19, 2026 ## Ready to book your vacation to Chester? Choose your dates ## Chester Hotel Deals ![The Piedmont Cabin - LPM](https://images.trvl-media.com/lodging/107000000/106140000/106134400/106134341/962b85b0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Piedmont Cabin - LPM Chester WV CA $189 CA $240 total Mar 8 - Mar 9 includes taxes & fees 10/10 Exceptional! (3 reviews) Perfect place! Reviewed on Nov 30, 2025 [](https://expedia.ca/Hotel-Search?startDate=08%2F03%2F2026&endDate=09%2F03%2F2026&selected=106134341&PinnedHotelID=106134341&HadPinnedHotel=true®ionId=55634) ![Hyatt Regency Pittsburgh International Airport](https://images.trvl-media.com/lodging/1000000/470000/464100/464013/1caa2404_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 CA $204 CA $232 total Feb 27 - Feb 28 includes taxes & fees 9/10 Wonderful! (1,608 reviews) Clean room, comfy bed and bedding. Reviewed on Feb 1, 2026 [](https://expedia.ca/Hotel-Search?startDate=27%2F02%2F2026&endDate=28%2F02%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/b3836cb9_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 CA $84 CA $96 total Feb 22 - Feb 23 includes taxes & fees 8/10 Very Good! (2,227 reviews) All was great Reviewed on Feb 5, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=2472&PinnedHotelID=2472&HadPinnedHotel=true®ionId=55634) [See all 151 properties in Chester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=07%2F02%2F2026&endDate=08%2F02%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. ![](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.ca/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.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## 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. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app