Title: Visit Chester Gap: Best of Chester Gap Tourism | Expedia Travel Guide - Expedia.ca [Hotels in Chester Gap](https://expedia.ca/Chester-Gap-Hotels.d553248635975865285.Travel-Guide-Hotels)[Vacation Rentals in Chester Gap](https://expedia.ca/Chester-Gap-Vacation-Rentals.d553248635975865285.Travel-Guide-VacationRentals)[Chester Gap Car Rentals](https://expedia.ca/Car-Rentals-In-Chester-Gap.d553248635975865285.Car-Rental-Guide)[Chester Gap Vacation Packages](https://expedia.ca/Chester-Gap.d553248635975865285.Destination-Travel-Guides) # Chester Gap ## Travel Guide ![Photo by Brian V. Rowe](https://mediaim.expedia.com/destination/2/a636e33b71dd87047fd3a46ed8933b8f.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Brian V. Rowe](https://mediaim.expedia.com/destination/2/a636e33b71dd87047fd3a46ed8933b8f.jpg) ![Photo by Brian V. Rowe](https://mediaim.expedia.com/destination/2/3693a13aef9836c5256bfe062da947d1.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Brian V. Rowe](https://mediaim.expedia.com/destination/2/3693a13aef9836c5256bfe062da947d1.jpg) ![Photo by Brian V. Rowe](https://mediaim.expedia.com/destination/2/b83bb6602399ec0fdb7e11b9ff676491.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Brian V. Rowe](https://mediaim.expedia.com/destination/2/b83bb6602399ec0fdb7e11b9ff676491.jpg) ## Visit Chester Gap - Chester Gap Hotel Deals - Vacation Rentals in Chester Gap ![Comfort Inn & Suites Winchester](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/cf4c2663_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Comfort Inn & Suites Winchester 195 Kernstown Commons Blvd Winchester VA CA $135 CA $147 total Jan 11 - Jan 12, 2026 includes taxes & fees Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ... 9.4/10 Exceptional! (1,072 reviews) Great accomodations!! Reviewed on Dec 6, 2025 [](https://expedia.ca/Hotel-Search?startDate=11%2F01%2F2026&endDate=12%2F01%2F2026&selected=57958244&PinnedHotelID=57958244&HadPinnedHotel=true®ionId=553248635975865285) ![Hampton Inn Front Royal](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/737257e0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn Front Royal 9800 Winchester Rd Front Royal VA CA $148 CA $164 total Dec 21 - Dec 22 includes taxes & fees Book a stay at this business-friendly hotel in Front Royal. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ... 9/10 Wonderful! (1,002 reviews) All great Reviewed on Dec 11, 2025 [](https://expedia.ca/Hotel-Search?startDate=21%2F12%2F2025&endDate=22%2F12%2F2025&selected=892585&PinnedHotelID=892585&HadPinnedHotel=true®ionId=553248635975865285) ![Country Inn & Suites by Radisson, Winchester, VA](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/d0690cde_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Country Inn & Suites by Radisson, Winchester, VA 141 Kernstown Commons Blvd Winchester VA CA $115 CA $125 total Jan 11 - Jan 12, 2026 includes taxes & fees Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ... 8.6/10 Excellent! (1,006 reviews) Room was large, very clean and very comfortable. Reviewed on Dec 7, 2025 [](https://expedia.ca/Hotel-Search?startDate=11%2F01%2F2026&endDate=12%2F01%2F2026&selected=1652833&PinnedHotelID=1652833&HadPinnedHotel=true®ionId=553248635975865285) [See all 511 properties in Chester Gap](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=14%2F12%2F2025&endDate=15%2F12%2F2025®ionId=553248635975865285) 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. !["Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub ](https://images.trvl-media.com/lodging/23000000/22250000/22243700/22243657/edab5469_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### "Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub Rileyville VA Stay at this cabin in Rileyville. Enjoy free WiFi, a garden, and laundry facilities. Our guests praise the property condition in our reviews. Popular attractions ... 9.8/10 Exceptional! (331 reviews) My husband and I stayed at The Walden from November 21st to November 23rd, and it was an unforgettable experience. The home was spotless, beautifully maintained, and thoughtfully designed inside and out. The views from the property are absolutely stunning, adding to the peaceful and romantic atmosphere.We ... Reviewed on Nov 23, 2025 [](https://expedia.ca/Rileyville-Hotels-Walden-Spectacular-Riverfront-Cabin-On-54-Acres-Whot-Tub-Near-Luray.h22243657.Hotel-Information) !["Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.](https://images.trvl-media.com/lodging/23000000/22260000/22255700/22255620/f116a78a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### "Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA. Rileyville VA Stay at this cabin in Rileyville. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Chalybeate Spring and Fort Valley Public Library are ... 10/10 Exceptional! (324 reviews) Appreciated the great communication the host provided. We REALLY appreciated just how clean the cabin was. It was such a nice cabin to stay in for a quick 2-night get-away. It was the perfect layout and size for a cozy place for just the two of us. Hot tub was wonderful (and so clean!!!). The firepit ... Reviewed on Nov 19, 2025 [](https://expedia.ca/Rileyville-Hotels-Solitude-Spectacular-1-BR-Cabin-W-Hot-Tub-Near-Luray.h22255620.Hotel-Information) ![The Vue - Mountain top hot tub overlooking the Shenandoah River](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/a69388d0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Vue - Mountain top hot tub overlooking the Shenandoah River Front Royal VA Stay at this cottage in Front Royal. Enjoy laundry facilities, patios, and an in-room coffeemaker. Popular attractions John T Shipe JR Park and Deer Lake are ... 9.8/10 Exceptional! (10 reviews) Wonderful stay! House was just as amazing as pictured, we had the best time for our girls trip! Can’t wait to come back!! Highly recommend. Reviewed on Nov 9, 2025 [](https://expedia.ca/Front-Royal-Hotels-The-Vue-Mountain-Top-Hot-Tub-Overlooking-The-Shenandoah-River.h107613898.Hotel-Information) [See all properties in Chester Gap](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=553248635975865285&sort=VACATION_RENTAL) 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. ## Check Chester Gap hotel availability [Tonight ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=2025-12-13&endDate=2025-12-14)[Dec 13 - Dec 14](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=2025-12-13&endDate=2025-12-14) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=2025-12-14&endDate=2025-12-15)[Dec 14 - Dec 15](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=2025-12-14&endDate=2025-12-15) [Next weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=19%2F12%2F2025&endDate=21%2F12%2F2025)[Dec 19 - Dec 21](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=19%2F12%2F2025&endDate=21%2F12%2F2025) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - [Hotels near Blue Ridge Shadows Golf Club ](https://www.expedia.ca/Blue-Ridge-Shadows-Golf-Club-Hotels.0-l553248621532661832-0.Travel-Guide-Filter-Hotels) - [Hotels near Dickey Ridge Visitor Center ](https://www.expedia.ca/Dickey-Ridge-Visitor-Center-Hotels.0-l553248621587527599-0.Travel-Guide-Filter-Hotels) - [Flint Hill Hotels ](https://www.expedia.ca/Flint-Hill-Hotels.d184090.Travel-Guide-Hotels) - [Rv Parks in Flint Hill ](https://www.expedia.ca/Flint-Hill-RV-Parks.d184090-aaRVParks.Travel-Guide-Accommodation) - [Resorts in Flint Hill ](https://www.expedia.ca/Flint-Hill-Resort-Hotels.d184090-aaResortHotels.Travel-Guide-Accommodation) - [B&B in Front Royal ](https://www.expedia.ca/Front-Royal-Bed-And-Breakfast.d7312-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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Places of interest - [Shenandoah National Park ](https://expedia.ca/Shenandoah-National-Park-Virginia.d6025893.Vacation-Attraction) - [Front Royal Entrance Shenandoah National Park ](https://expedia.ca/Front-Royal-Entrance-Shenandoah-National-Park-Front-Royal.d6129961.Vacation-Attraction) - [Skyline Caverns ](https://expedia.ca/Skyline-Caverns-Front-Royal.d6093201.Vacation-Attraction) - [Mary's Rock Summit Trailhead ](https://expedia.ca/Marys-Rock-Summit-Trailhead-Luray.d553248621532661700.Vacation-Attraction) - [Naked Mountain Winery & Vineyards ](https://expedia.ca/Naked-Mountain-Winery-Vineyards-Delaplane.d553248621532661859.Vacation-Attraction) ![](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. 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