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 - 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 Fully refundable $102 nightly $111 total Apr 22 - Apr 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) Great location; easy access off hwy. Very nice staff; clean room; comfortable beds and nice breakfast! Reviewed on Mar 20, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F22%2F2026&endDate=4%2F23%2F2026&selected=57958244&PinnedHotelID=57958244&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 $116 total Apr 12 - Apr 13 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) All the staff members were so nice and kind!! The hotel room I booked were very clean and spotless, and the breakfast was even fresh too! Reviewed on Mar 21, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F12%2F2026&endDate=4%2F13%2F2026&selected=892585&PinnedHotelID=892585&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 $86 total Mar 30 - Mar 31 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! (1,000 reviews) Was a nice stay had a great time at the little restaurant Reviewed on Mar 17, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F30%2F2026&endDate=3%2F31%2F2026&selected=1246311&PinnedHotelID=1246311&HadPinnedHotel=true®ionId=553248635975865285) [See all 510 properties in Chester Gap](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=3%2F23%2F2026&endDate=3%2F24%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! (342 reviews) Amazing place Reviewed on Mar 18, 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! (181 reviews) Host was very responsive and helpful. House was very clean. Loved the layout and decor. It was wonderful being right in the mountains in such a sweet, secluded and very homie, comfortable place. We will definitely try to book again in the future! Reviewed on Mar 5, 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=2026-03-22&endDate=2026-03-23)[Mar 22 - Mar 23](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=2026-03-22&endDate=2026-03-23) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=2026-03-23&endDate=2026-03-24)[Mar 23 - Mar 24](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=2026-03-23&endDate=2026-03-24) [Next weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=3%2F27%2F2026&endDate=3%2F29%2F2026)[Mar 27 - Mar 29](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=3%2F27%2F2026&endDate=3%2F29%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) - [Thorton Gap Entrance Shenandoah ](https://expedia.com/Thorton-Gap-Entrance-Shenandoah-Luray.d6129963.Vacation-Attraction) - [George Washington National Forest ](https://expedia.com/George-Washington-National-Forest-United-States-of-America.d6160906.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) - [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) - [Front Royal Visitor's Center ](https://expedia.com/Front-Royal-Visitors-Center-Front-Royal.d553248621532661829.Vacation-Attraction) - [Little Washington Winery ](https://expedia.com/Little-Washington-Winery-Washington.d553248621532661811.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) - [Dinosaur Land ](https://expedia.com/Dinosaur-Land-White-Post.d553248621532661835.Vacation-Attraction) - [Belle Grove Plantation ](https://expedia.com/Belle-Grove-Plantation-Middletown.d6164020.Vacation-Attraction) - [RdV Vineyards ](https://expedia.com/RdV-Vineyards-Delaplane.d553248621532661862.Vacation-Attraction) - [Linden Vineyards ](https://expedia.com/Linden-Vineyards-Linden.d553248621532661830.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) - [Valerie Hill Winery ](https://expedia.com/Valerie-Hill-Winery-Stephens-City.d553248621532661834.Vacation-Attraction) - [Copper Fox Distillery ](https://expedia.com/Copper-Fox-Distillery-Sperryville.d553248621532661751.Vacation-Attraction) - [Woodstock Tower Observation Site ](https://expedia.com/Woodstock-Tower-Observation-Site-Woodstock.d553248621561864668.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) - [Virginia River Trips ](https://expedia.com/Virginia-River-Trips-White-Post.d553248621532661838.Vacation-Attraction) - [State Arboretum of Virginia ](https://expedia.com/State-Arboretum-Of-Virginia-Virginia.d6164038.Vacation-Attraction) - [Barrel Oak Winery ](https://expedia.com/Barrel-Oak-Winery-Marshall.d553248621532661861.Vacation-Attraction) - [Delaplane Cellars ](https://expedia.com/Delaplane-Cellars-Delaplane.d553248621532661863.Vacation-Attraction) - [Strasburg Town Hall ](https://expedia.com/Strasburg-Town-Hall-Strasburg.d553248621532661821.Vacation-Attraction) - [Pinnacles ](https://expedia.com/Pinnacles-Sperryville.d553248621532661749.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. Scan the QR code with your device camera and download our app