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) ![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 Mar 22 - Mar 23 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! (1,091 reviews) Best hotel we have been in in a long time-a repeat!! Clean, everything worked, great friendly staff. Reviewed on Mar 14, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F22%2F2026&endDate=3%2F23%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 $77 nightly $85 total Mar 22 - Mar 23 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! (1,001 reviews) Our room was clean and the two staff members I spoke with were friendly. Reviewed on Mar 14, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F22%2F2026&endDate=3%2F23%2F2026&selected=1246311&PinnedHotelID=1246311&HadPinnedHotel=true®ionId=553248635975865285) ![Hampton Inn Front Royal](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/810f7f7f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn Front Royal 9800 Winchester Rd Front Royal VA $104 nightly $115 total Mar 29 - Mar 30 Total with taxes and 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! (1,001 reviews) Excellent Reviewed on Mar 15, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=892585&PinnedHotelID=892585&HadPinnedHotel=true®ionId=553248635975865285) [See all 508 properties in Chester Gap](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=3%2F16%2F2026&endDate=3%2F17%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) !["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! (347 reviews) This cabin is as exactly as promised. It is the perfect secluded retreat and getaway location. The amenities and house are well taken care of. During our stay, we had an issue with the hot water. In this day and age, it would be so easy to lose your cool, but we can't say enough about how responsive ... Reviewed on Feb 18, 2026 [](https://expedia.com/Rileyville-Hotels-Solitude-Spectacular-1-BR-Cabin-W-Hot-Tub-Near-Luray.h22255620.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) [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=2026-03-15&endDate=2026-03-16)[Mar 15 - Mar 16](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=2026-03-15&endDate=2026-03-16) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=2026-03-16&endDate=2026-03-17)[Mar 16 - Mar 17](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=2026-03-16&endDate=2026-03-17) [Next weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=3%2F20%2F2026&endDate=3%2F22%2F2026)[Mar 20 - Mar 22](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=3%2F20%2F2026&endDate=3%2F22%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) - [Thorton Gap Entrance Shenandoah ](https://expedia.com/Thorton-Gap-Entrance-Shenandoah-Luray.d6129963.Vacation-Attraction) - [Shenandoah River ](https://expedia.com/Shenandoah-River-Virginia.d681974697590321152.Vacation-Attraction) - [Yogi Bear's Jellystone Park ](https://expedia.com/Yogi-Bears-Jellystone-Park-Luray.d553248621561864671.Vacation-Attraction) - [Skyline Caverns ](https://expedia.com/Skyline-Caverns-Front-Royal.d6093201.Vacation-Attraction) - [Shenandoah River State Park ](https://expedia.com/Shenandoah-River-State-Park-Bentonville.d553248621532661809.Vacation-Attraction) - [Mary's Rock Summit Trailhead ](https://expedia.com/Marys-Rock-Summit-Trailhead-Luray.d553248621532661700.Vacation-Attraction) - [Dinosaur Land ](https://expedia.com/Dinosaur-Land-White-Post.d553248621532661835.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) - [Dickey Ridge Visitor Center ](https://expedia.com/Dickey-Ridge-Visitor-Center-Front-Royal.d553248621587527599.Vacation-Attraction) - [RdV Vineyards ](https://expedia.com/RdV-Vineyards-Delaplane.d553248621532661862.Vacation-Attraction) - [Copper Fox Distillery ](https://expedia.com/Copper-Fox-Distillery-Sperryville.d553248621532661751.Vacation-Attraction) - [Pinnacles ](https://expedia.com/Pinnacles-Sperryville.d553248621532661749.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) - [Delaplane Cellars ](https://expedia.com/Delaplane-Cellars-Delaplane.d553248621532661863.Vacation-Attraction) - [Naked Mountain Winery & Vineyards ](https://expedia.com/Naked-Mountain-Winery-Vineyards-Delaplane.d553248621532661859.Vacation-Attraction) - [Little Washington Theatre ](https://expedia.com/Little-Washington-Theatre-Washington.d553248621587586984.Vacation-Attraction) - [River District Arts ](https://expedia.com/River-District-Arts-Sperryville.d553248621532661750.Vacation-Attraction) - [Virginia River Trips ](https://expedia.com/Virginia-River-Trips-White-Post.d553248621532661838.Vacation-Attraction) - [Valerie Hill Winery ](https://expedia.com/Valerie-Hill-Winery-Stephens-City.d553248621532661834.Vacation-Attraction) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save even more - 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