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 $136 CA $148 total Oct 20 - Oct 21 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! (1,019 reviews) "The breakfast was good and a quiet place to stay" Reviewed on Oct 13, 2025 [](https://expedia.ca/Hotel-Search?startDate=20%2F10%2F2025&endDate=21%2F10%2F2025&selected=57958244&PinnedHotelID=57958244&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 $128 CA $139 total Nov 9 - Nov 10 includes taxes & fees Stay at this 3-star 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! (1,017 reviews) "Nice hotel! Breakfast needs work" Reviewed on Oct 14, 2025 [](https://expedia.ca/Hotel-Search?startDate=09%2F11%2F2025&endDate=10%2F11%2F2025&selected=1652833&PinnedHotelID=1652833&HadPinnedHotel=true®ionId=553248635975865285) ![Ramada by Wyndham Strasburg/Shenandoah Valley](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/08da8378_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Ramada by Wyndham Strasburg/Shenandoah Valley 21 Signal Knob Dr, GPS: 35 Brandy court, Strasburg, VA CA $113 CA $126 total Oct 26 - Oct 27 includes taxes & fees Book a stay at this business-friendly hotel in Strasburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ... 8.2/10 Very Good! (1,022 reviews) "Stayed here while on a golf trip with friends. Was very please with every aspect of stay. Tex-Mex cantina adjacent to hotel was excellent food and drink without having to leave hotel. Will definitely stay there again." Reviewed on Oct 12, 2025 [](https://expedia.ca/Hotel-Search?startDate=26%2F10%2F2025&endDate=27%2F10%2F2025&selected=1246311&PinnedHotelID=1246311&HadPinnedHotel=true®ionId=553248635975865285) [See all 509 properties in Chester Gap](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=18%2F10%2F2025&endDate=19%2F10%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 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 ... 10/10 Exceptional! (322 reviews) "Great place!" Reviewed on Sep 25, 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 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! (319 reviews) "Beautiful pet friendly cabin perfectly named as Solitude. I needed a place to get away from the city for a quick weekend getaway with my dog and it was perfect. I enjoyed sitting in the sun in the chairs around the fire pit, the hot tub, and just easing into my day watching the sun come up on the ..." Reviewed on Sep 21, 2025 [](https://expedia.ca/Rileyville-Hotels-Solitude-Spectacular-1-BR-Cabin-W-Hot-Tub-Near-Luray.h22255620.Hotel-Information) ![Star view cabin-Riverfront ](https://images.trvl-media.com/lodging/31000000/30790000/30788500/30788475/2cb5e40f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Star view cabin-Riverfront Rileyville Stay at this cabin in Rileyville. Enjoy laundry facilities, tennis courts, and patios. Our guests praise the property condition in our reviews. Popular attractions ... 9.8/10 Exceptional! (300 reviews) "This property is in a beautiful and very peaceful location. It was very clean. I would 100% recommend this cabin to anyone who will be staying in or around the Rileyville area, you will not be disappointed." Reviewed on Oct 11, 2025 [](https://expedia.ca/Rileyville-Hotels-Star-View-Cabin-Riverfront.h30788475.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 [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=2025-10-17&endDate=2025-10-18) [Tonight](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=2025-10-17&endDate=2025-10-18) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=2025-10-17&endDate=2025-10-18) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=2025-10-17&endDate=2025-10-18)[Oct 17 - Oct 18](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=2025-10-17&endDate=2025-10-18) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=2025-10-18&endDate=2025-10-19) [Tomorrow night](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=2025-10-18&endDate=2025-10-19) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=2025-10-18&endDate=2025-10-19) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=2025-10-18&endDate=2025-10-19)[Oct 18 - Oct 19](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=2025-10-18&endDate=2025-10-19) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=17%2F10%2F2025&endDate=19%2F10%2F2025) [This weekend](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=17%2F10%2F2025&endDate=19%2F10%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=17%2F10%2F2025&endDate=19%2F10%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=17%2F10%2F2025&endDate=19%2F10%2F2025)[Oct 17 - Oct 19](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=17%2F10%2F2025&endDate=19%2F10%2F2025) ## Explore a world of travel with Expedia - 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[Car rentals in Avis 17375 Collins Ave-Doubletree Hotel Lobby](https://www.expedia.ca/Avis-at-17375-Collins-Ave-Doubletree-Hotel-Lobby-Sunny-Isles-Beach-Florida-USA.v56034.Car-Rental-Guide-Location) - [Budget Rental Cars in Front Royal](https://www.expedia.ca/Budget-Car-Rentals-In-Front-Royal.d7312-c39.Car-Rental-Guide-Suppliers) - [Car rental Front Royal](https://www.expedia.ca/Car-Rentals-In-Front-Royal.d7312.Car-Rental-Guide) - Cities near Chester Gap - 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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