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 ![Many butterflies ](https://images.trvl-media.com/place/553248635975865285/f9238aa1-8e19-4f36-bc38-1a5bd9663644.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Many butterflies ](https://images.trvl-media.com/place/553248635975865285/f9238aa1-8e19-4f36-bc38-1a5bd9663644.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Summer colors](https://images.trvl-media.com/place/553248635975865285/83f369c4-f3a4-4677-9f0c-11b418e7ecb8.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Pretty](https://images.trvl-media.com/place/553248635975865285/cca81612-f52b-42d0-bc80-70a7b4e1cd7e.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ## Visit Chester Gap - Chester Gap Hotel Deals - Vacation Rentals in Chester Gap ![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 Strasburg VA CA $104 CA $115 total Feb 2 - Feb 3 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! (1,000 reviews) Great stay everyone friendly will stay again Reviewed on Jan 19, 2026 [](https://expedia.ca/Hotel-Search?startDate=02%2F02%2F2026&endDate=03%2F02%2F2026&selected=1246311&PinnedHotelID=1246311&HadPinnedHotel=true®ionId=553248635975865285) ![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 $134 CA $146 total Feb 22 - Feb 23 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! (1,098 reviews) All of the above Reviewed on Jan 21, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=57958244&PinnedHotelID=57958244&HadPinnedHotel=true®ionId=553248635975865285) ![DoubleTree by Hilton Front Royal Blue Ridge Shadows](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/204cbf3a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### DoubleTree by Hilton Front Royal Blue Ridge Shadows 111 Hospitality Drive Front Royal VA CA $134 CA $147 total Feb 8 - Feb 9 includes taxes & fees Book a stay at this golf hotel in Front Royal. Enjoy free WiFi, free parking, and a golf course. Our guests praise the helpful staff and the clean rooms in our ... 8.8/10 Excellent! (1,000 reviews) Great room and staff. Nice restaurant and bar also with good prices. Very nice hotel. 5 stars Reviewed on Jan 15, 2026 [](https://expedia.ca/Hotel-Search?startDate=08%2F02%2F2026&endDate=09%2F02%2F2026&selected=1889081&PinnedHotelID=1889081&HadPinnedHotel=true®ionId=553248635975865285) [See all 512 properties in Chester Gap](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=28%2F01%2F2026&endDate=29%2F01%2F2026®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. ![Falling Leaf Cabin - Rustic Charm With Modern Decor!](https://images.trvl-media.com/lodging/34000000/33750000/33748300/33748224/e001c092_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Falling Leaf Cabin - Rustic Charm With Modern Decor! Rileyville VA Book a stay at this family-friendly cabin in Rileyville. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Chalybeate Spring and Fort Valley ... 9.6/10 Exceptional! (281 reviews) It was very nice, peaceful and relaxing! Very cozy. Had everything we needed. Great view too! Reviewed on Dec 8, 2025 [](https://expedia.ca/Rileyville-Hotels-Falling-Leaf-Cabin-Secluded-With-Mountain-View.h33748224.Hotel-Information) ![Riverfront🏕A-Frame/HOT TUB/Fire Pit! FAST Wifi](https://images.trvl-media.com/lodging/77000000/76940000/76936100/76936006/8f9a845e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Riverfront🏕A-Frame/HOT TUB/Fire Pit! FAST Wifi Maurertown VA Stay at this cabin in Maurertown. Enjoy laundry facilities, patios, and cable/satellite TV service. Popular attractions Shenandoah County Park and Natural Art ... 9.8/10 Exceptional! (80 reviews) No problems with the internet, loved tge temperature in the hit tub, available wood fir the firepit. The game room with nice. The kitchen was well furnanced. If i had a question or problem, the owner was very attentive. Its a drive to get there but its worth it! Reviewed on Jan 17, 2026 [](https://expedia.ca/Maurertown-Hotels-RiverfrontA-Frame-King-Bed-Fire-Pit150mbs-Wifi.h76936006.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 VA Stay at this cabin in Rileyville. Enjoy laundry facilities, tennis courts, and patios. Our guests praise the property condition in our reviews. Popular attractions ... 9.6/10 Exceptional! (310 reviews) Excellent location, wonderful home and view. How was very responsive, no service/wifi was tough Reviewed on Jan 6, 2026 [](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 [Tonight ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=2026-01-27&endDate=2026-01-28)[Jan 27 - Jan 28](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=2026-01-27&endDate=2026-01-28) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=2026-01-28&endDate=2026-01-29)[Jan 28 - Jan 29](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=2026-01-28&endDate=2026-01-29) [This weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=30%2F01%2F2026&endDate=01%2F02%2F2026)[Jan 30 - Feb 1](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=30%2F01%2F2026&endDate=01%2F02%2F2026) [Next weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=06%2F02%2F2026&endDate=08%2F02%2F2026)[Feb 6 - Feb 8](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=06%2F02%2F2026&endDate=08%2F02%2F2026) ## 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) - 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