Title: Visit Chester Gap: 2026 Travel Guide for Chester Gap, Virginia | Expedia.com [Hotels in Chester Gap](https://expedia.com/Chester-Gap-Hotels.d553248635975865285.Travel-Guide-Hotels)[Vacation Rentals in Chester Gap](https://expedia.com/Chester-Gap-Vacation-Rentals.d553248635975865285.Travel-Guide-VacationRentals)[Car Rentals in Chester Gap](https://expedia.com/Car-Rentals-In-Chester-Gap.d553248635975865285.Car-Rental-Guide)[Chester Gap Vacation Packages](https://expedia.com/Chester-Gap.d553248635975865285.Destination-Travel-Guides) # Chester Gap, VA ## 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) ## Visit Chester Gap ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=DX_SPRING_PROMO_553248635975865285) - 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 $101 nightly $110 total Apr 6 - Apr 7 Total with taxes and 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! (1,101 reviews) Room was great. Front desk man was very friendly and gracious. Breakfast was fine, staff friendly, and a great job of keeping everything spotless. Bob Stanley Reviewed on Mar 2, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F6%2F2026&endDate=4%2F7%2F2026&selected=57958244&PinnedHotelID=57958244&HadPinnedHotel=true®ionId=553248635975865285) ![Ramada by Wyndham Strasburg/Shenandoah Valley](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/220661a2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Ramada by Wyndham Strasburg/Shenandoah Valley 21 Signal Knob Dr Strasburg VA $78 nightly $87 total Mar 15 - Mar 16 Total with taxes and 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 ... 8.4/10 Very Good! (1,008 reviews) Did not have a pool or arcade like the website said... Reviewed on Mar 6, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F15%2F2026&endDate=3%2F16%2F2026&selected=1246311&PinnedHotelID=1246311&HadPinnedHotel=true®ionId=553248635975865285) ![Country Inn & Suites by Radisson, Winchester, VA](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/a391dd61_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Country Inn & Suites by Radisson, Winchester, VA 141 Kernstown Commons Blvd Winchester VA $91 nightly $99 total Mar 15 - Mar 16 Total with taxes and 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 ... 8.8/10 Excellent! (1,002 reviews) Convenient location, clean room, and nice breakfast Reviewed on Mar 1, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F15%2F2026&endDate=3%2F16%2F2026&selected=1652833&PinnedHotelID=1652833&HadPinnedHotel=true®ionId=553248635975865285) [See all 512 properties in Chester Gap](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=3%2F8%2F2026&endDate=3%2F9%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! Newly Renovated Kitchen!](https://images.trvl-media.com/lodging/34000000/33750000/33748300/33748224/4a09aa4b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Falling Leaf Cabin - Rustic Charm With Modern Decor! Newly Renovated Kitchen! 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 ... 9.8/10 Exceptional! (308 reviews) The cabin was cozy and warm in this wintry weather. The host was easy to communicate with and everything went smoothly. Reviewed on Feb 18, 2026 [](https://expedia.com/Rileyville-Hotels-Falling-Leaf-Cabin-Secluded-With-Mountain-View.h33748224.Hotel-Information) ![Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo](https://images.trvl-media.com/lodging/27000000/26970000/26968400/26968349/88605fc6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo Front Royal VA Stay at this cabin in Front Royal. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Glen Manor Vineyards and Shenandoah River State Park ... 9.6/10 Exceptional! (341 reviews) Beautiful view could not be beat and the cabin was cozy. Enjoyed playing some of the board games there and the fireplace. Host was quick to respond whenever we messaged. Reviewed on Mar 3, 2026 [](https://expedia.com/Front-Royal-Hotels-Log-Cabin-With-A-Spectacular-View-Of-The-Shenandoah-River-And-The-Massanutten-Mo.h26968349.Hotel-Information) ![Secluded River Cabin Getaway (Masten Cabin)](https://images.trvl-media.com/lodging/58000000/57920000/57914400/57914375/79bbd46a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Secluded River Cabin Getaway (Masten Cabin) Strasburg VA Stay at this vacation home in Strasburg. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Secret Passage Ranch and Strasburg Museum are located ... 9.8/10 Exceptional! (180 reviews) Had everything we needed to feel at home great location we will be booking again Reviewed on Mar 2, 2026 [](https://expedia.com/Strasburg-Hotels-Secluded-River-Cabin-Getaway.h57914375.Hotel-Information) [See all properties in Chester Gap](https://expedia.com/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.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=2026-03-07&endDate=2026-03-08)[Mar 7 - Mar 8](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=2026-03-07&endDate=2026-03-08) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=2026-03-08&endDate=2026-03-09)[Mar 8 - Mar 9](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=2026-03-08&endDate=2026-03-09) [Next weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=3%2F13%2F2026&endDate=3%2F15%2F2026)[Mar 13 - Mar 15](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=3%2F13%2F2026&endDate=3%2F15%2F2026) ## Cities near Chester Gap ![Trees - Bear Church Rock Trail, Shenandoah National Park, Virginia](https://images.trvl-media.com/place/7312/1e808d74-e702-47a6-a388-ce77751dfd04.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Front Royal ![Grass fields with sheep in the countryside with hills in the background ](https://images.trvl-media.com/place/3000460054/0bfddc8d-2c48-49f8-80e2-0e6081b8b74b.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Huntly - Cities near Chester Gap - Places of interest [Front Royal](https://expedia.com/Front-Royal.dx7312)[Huntly](https://expedia.com/Huntly.dx3000460054) - [Shenandoah National Park ](https://expedia.com/Shenandoah-National-Park-Virginia.d6025893.Vacation-Attraction) - [Front Royal Entrance Shenandoah National Park ](https://expedia.com/Front-Royal-Entrance-Shenandoah-National-Park-Front-Royal.d6129961.Vacation-Attraction) - [George Washington National Forest ](https://expedia.com/George-Washington-National-Forest-United-States-of-America.d6160906.Vacation-Attraction) - [Yogi Bear's Jellystone Park ](https://expedia.com/Yogi-Bears-Jellystone-Park-Luray.d553248621561864671.Vacation-Attraction) - [Shenandoah River ](https://expedia.com/Shenandoah-River-Virginia.d681974697590321152.Vacation-Attraction) - [Thorton Gap Entrance Shenandoah ](https://expedia.com/Thorton-Gap-Entrance-Shenandoah-Luray.d6129963.Vacation-Attraction) - [Shenandoah River State Park ](https://expedia.com/Shenandoah-River-State-Park-Bentonville.d553248621532661809.Vacation-Attraction) - [Skyline Caverns ](https://expedia.com/Skyline-Caverns-Front-Royal.d6093201.Vacation-Attraction) - [Dinosaur Land ](https://expedia.com/Dinosaur-Land-White-Post.d553248621532661835.Vacation-Attraction) - [Mary's Rock Summit Trailhead ](https://expedia.com/Marys-Rock-Summit-Trailhead-Luray.d553248621532661700.Vacation-Attraction) - [Sky Meadows State Park ](https://expedia.com/Sky-Meadows-State-Park-Virginia.d553248621532661864.Vacation-Attraction) - [Little Washington Winery ](https://expedia.com/Little-Washington-Winery-Washington.d553248621532661811.Vacation-Attraction) - [Belle Grove Plantation ](https://expedia.com/Belle-Grove-Plantation-Middletown.d6164020.Vacation-Attraction) - [Front Royal Visitor's Center ](https://expedia.com/Front-Royal-Visitors-Center-Front-Royal.d553248621532661829.Vacation-Attraction) - [Linden Vineyards ](https://expedia.com/Linden-Vineyards-Linden.d553248621532661830.Vacation-Attraction) - [Woodstock Tower Observation Site ](https://expedia.com/Woodstock-Tower-Observation-Site-Woodstock.d553248621561864668.Vacation-Attraction) - [RdV Vineyards ](https://expedia.com/RdV-Vineyards-Delaplane.d553248621532661862.Vacation-Attraction) - [Pinnacles ](https://expedia.com/Pinnacles-Sperryville.d553248621532661749.Vacation-Attraction) - [Dickey Ridge Visitor Center ](https://expedia.com/Dickey-Ridge-Visitor-Center-Front-Royal.d553248621587527599.Vacation-Attraction) - [Naked Mountain Winery & Vineyards ](https://expedia.com/Naked-Mountain-Winery-Vineyards-Delaplane.d553248621532661859.Vacation-Attraction) - [Copper Fox Distillery ](https://expedia.com/Copper-Fox-Distillery-Sperryville.d553248621532661751.Vacation-Attraction) - [Delaplane Cellars ](https://expedia.com/Delaplane-Cellars-Delaplane.d553248621532661863.Vacation-Attraction) - [Virginia River Trips ](https://expedia.com/Virginia-River-Trips-White-Post.d553248621532661838.Vacation-Attraction) - [Cedar Creek and Belle Grove National Historical Park ](https://expedia.com/Cedar-Creek-And-Belle-Grove-National-Historical-Park-Middletown.d6093271.Vacation-Attraction) - [Chester Gap Cellars ](https://expedia.com/Chester-Gap-Cellars-Huntly.d553248621587527596.Vacation-Attraction) - [Glen Manor Vineyards ](https://expedia.com/Glen-Manor-Vineyards-Front-Royal.d553248621587527610.Vacation-Attraction) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save even more - get up to 20% on select hotels 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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