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 ![Chester Gap](https://images.trvl-media.com/place/553248635975865285/f9238aa1-8e19-4f36-bc38-1a5bd9663644.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Chester Gap](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 $103 nightly $112 total Apr 27 - Apr 28 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! (1,094 reviews) We enjoyed having a large room with a sofa but found numerous dog hairs and human hair in towels and carpet. My grandson is allergic to certain dogs and he coughed the entire 3 days. Reviewed on Apr 4, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F27%2F2026&endDate=4%2F28%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 $79 nightly $88 total Apr 15 - Apr 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! (1,005 reviews) Nice Reviewed on Apr 4, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F15%2F2026&endDate=4%2F16%2F2026&selected=1246311&PinnedHotelID=1246311&HadPinnedHotel=true®ionId=553248635975865285) ![Hampton Inn Front Royal](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/w3840h2556x0y4-810f7f7f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn Front Royal 9800 Winchester Rd Front Royal VA $98 nightly $109 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) Friendly and helpful staff; great free breakfast - my kids loved making their own waffles! Reviewed on Apr 4, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F12%2F2026&endDate=4%2F13%2F2026&selected=892585&PinnedHotelID=892585&HadPinnedHotel=true®ionId=553248635975865285) [See all 517 properties in Chester Gap](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=4%2F5%2F2026&endDate=4%2F6%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! (351 reviews) Everything was absolutely amazing! Thank you! Reviewed on Apr 3, 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! (344 reviews) Amazing views! Comfortable and clean. Excellent communications with host. Great location. Highly recommend! Reviewed on Apr 2, 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=2026-04-04&endDate=2026-04-05)[Apr 4 - Apr 5](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=2026-04-04&endDate=2026-04-05) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=2026-04-05&endDate=2026-04-06)[Apr 5 - Apr 6](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=2026-04-05&endDate=2026-04-06) [Next weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=4%2F10%2F2026&endDate=4%2F12%2F2026)[Apr 10 - Apr 12](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975865285&startDate=4%2F10%2F2026&endDate=4%2F12%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) - [Thorton Gap Entrance Shenandoah ](https://expedia.com/Thorton-Gap-Entrance-Shenandoah-Luray.d6129963.Vacation-Attraction) - [Front Royal Entrance Shenandoah National Park ](https://expedia.com/Front-Royal-Entrance-Shenandoah-National-Park-Front-Royal.d6129961.Vacation-Attraction) - [Shenandoah River ](https://expedia.com/Shenandoah-River-Virginia.d681974697590321152.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) - [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) - [Little Washington Winery ](https://expedia.com/Little-Washington-Winery-Washington.d553248621532661811.Vacation-Attraction) - [Sky Meadows State Park ](https://expedia.com/Sky-Meadows-State-Park-Virginia.d553248621532661864.Vacation-Attraction) - [Mary's Rock Summit Trailhead ](https://expedia.com/Marys-Rock-Summit-Trailhead-Luray.d553248621532661700.Vacation-Attraction) - [Front Royal Visitor's Center ](https://expedia.com/Front-Royal-Visitors-Center-Front-Royal.d553248621532661829.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) - [Linden Vineyards ](https://expedia.com/Linden-Vineyards-Linden.d553248621532661830.Vacation-Attraction) - [RdV Vineyards ](https://expedia.com/RdV-Vineyards-Delaplane.d553248621532661862.Vacation-Attraction) - [Naked Mountain Winery & Vineyards ](https://expedia.com/Naked-Mountain-Winery-Vineyards-Delaplane.d553248621532661859.Vacation-Attraction) - [Dickey Ridge Visitor Center ](https://expedia.com/Dickey-Ridge-Visitor-Center-Front-Royal.d553248621587527599.Vacation-Attraction) - [Secret Passage Ranch ](https://expedia.com/Secret-Passage-Ranch-Fort-Valley.d553248621561864680.Vacation-Attraction) - [Valerie Hill Winery ](https://expedia.com/Valerie-Hill-Winery-Stephens-City.d553248621532661834.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) - [State Arboretum of Virginia ](https://expedia.com/State-Arboretum-Of-Virginia-Virginia.d6164038.Vacation-Attraction) - [Woodstock Tower Observation Site ](https://expedia.com/Woodstock-Tower-Observation-Site-Woodstock.d553248621561864668.Vacation-Attraction) - [Copper Fox Distillery ](https://expedia.com/Copper-Fox-Distillery-Sperryville.d553248621532661751.Vacation-Attraction) - [Barrel Oak Winery ](https://expedia.com/Barrel-Oak-Winery-Marshall.d553248621532661861.Vacation-Attraction) - [Strasburg Town Hall ](https://expedia.com/Strasburg-Town-Hall-Strasburg.d553248621532661821.Vacation-Attraction) - [Pinnacles ](https://expedia.com/Pinnacles-Sperryville.d553248621532661749.Vacation-Attraction)