Title: Chester Gap Vacation Rentals from $223: Search Short-Term Rentals | Expedia.com [Hotels in Chester Gap](https://expedia.com/Chester-Gap-Hotels.d553248635975865285.Travel-Guide-Hotels)[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) ![Lodging Image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Mar 6 - Mar 8](https://www.expedia.com/Hotel-Search?regionId=553248635975865285&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=553248635975865285&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 15 - May 17](https://www.expedia.com/Hotel-Search?regionId=553248635975865285&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 12 - Jun 14](https://www.expedia.com/Hotel-Search?regionId=553248635975865285&startDate=2026-06-12&endDate=2026-06-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester Gap vacation rentals ![Property grounds](https://images.trvl-media.com/lodging/75000000/74080000/74077300/74077247/92815ab7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/75000000/74080000/74077300/74077247/f9fe7afa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/75000000/74080000/74077300/74077247/16f6f354.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/75000000/74080000/74077300/74077247/435bb49d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blue Mountain Cabin, secluded, perfect for couples, near main road [](https://www.expedia.com/Front-Royal-Hotels-Blue-Mountain-Cabin.h74077247.Hotel-Information) Front Royal 10/10 Exceptional (29 reviews) "Very cozy cabin for two, great for a secluded getaway within range of great places to visit. Had everything we needed." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tom C. $212 nightly $234 total Feb 19 - Feb 20 Total with taxes and fees [](https://www.expedia.com/Front-Royal-Hotels-Blue-Mountain-Cabin.h74077247.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/28000000/27480000/27477100/27477055/e1c41382.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/28000000/27480000/27477100/27477055/633fd344.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/28000000/27480000/27477100/27477055/b23ff435.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/28000000/27480000/27477100/27477055/d4045727.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stepping Stone Cabin [](https://www.expedia.com/Luray-Hotels-Stepping-Stone-Cabin.h27477055.Hotel-Information) Page County 9.8/10 Exceptional (48 reviews) "awesome stay we will love to go again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mark C. $323 nightly $357 total Feb 19 - Feb 20 Total with taxes and fees [](https://www.expedia.com/Luray-Hotels-Stepping-Stone-Cabin.h27477055.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/22000000/21480000/21478100/21478041/3b7c41d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/22000000/21480000/21478100/21478041/310143cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/22000000/21480000/21478100/21478041/aa284bd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/22000000/21480000/21478100/21478041/47a00baa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### "The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA [](https://www.expedia.com/Rileyville-Hotels-The-Chalet-Shenandoah-Valley-Getaway-W-Hot-Tub-Near-Luray.h21478041.Hotel-Information) Rileyville 9.8/10 Exceptional (314 reviews) "beautiful cabin, we wish we could have stayed longer! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Trisha L. $232 nightly $268 total Feb 22 - Feb 23 Total with taxes and fees [](https://www.expedia.com/Rileyville-Hotels-The-Chalet-Shenandoah-Valley-Getaway-W-Hot-Tub-Near-Luray.h21478041.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/23000000/22260000/22255700/22255620/f116a78a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/23000000/22260000/22255700/22255620/2dc032bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/23000000/22260000/22255700/22255620/64d9b733.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/23000000/22260000/22255700/22255620/f2ef318b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### "Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA. [](https://www.expedia.com/Rileyville-Hotels-Solitude-Spectacular-1-BR-Cabin-W-Hot-Tub-Near-Luray.h22255620.Hotel-Information) Rileyville 10/10 Exceptional (345 reviews) "Everything was perfect for our stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Debbie O. $231 nightly $266 total Feb 19 - Feb 20 Total with taxes and fees [](https://www.expedia.com/Rileyville-Hotels-Solitude-Spectacular-1-BR-Cabin-W-Hot-Tub-Near-Luray.h22255620.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/19000000/18950000/18940200/18940115/85f00100.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace, DVD player](https://images.trvl-media.com/lodging/19000000/18950000/18940200/18940115/a0354368.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/18950000/18940200/18940115/e8a0fd90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18950000/18940200/18940115/24a0d857.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Overlook Mountain Cabin [](https://www.expedia.com/Rileyville-Hotels-Overlook-Mountain-Cabin.h18940115.Hotel-Information) Page County 9.8/10 Exceptional (164 reviews) "We loved this little cabin. It’s extremely comfortable and the view is spectacular (and you can enjoy it from the hot tub !) Unless you have a4-wheel drive with good clearance, we recommend taking one of the Jeeps the owner offers up to the house. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) sara r. $386 nightly $427 total Feb 23 - Feb 24 Total with taxes and fees [](https://www.expedia.com/Rileyville-Hotels-Overlook-Mountain-Cabin.h18940115.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/23000000/22250000/22243700/22243657/edab5469.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/23000000/22250000/22243700/22243657/f7fc0dd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/23000000/22250000/22243700/22243657/0c19b755.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/23000000/22250000/22243700/22243657/b116227a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### "Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub [](https://www.expedia.com/Rileyville-Hotels-Walden-Spectacular-Riverfront-Cabin-On-54-Acres-Whot-Tub-Near-Luray.h22243657.Hotel-Information) Rileyville 10/10 Exceptional (355 reviews) "Great place!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donald C. $231 nightly $266 total Feb 19 - Feb 20 Total with taxes and fees [](https://www.expedia.com/Rileyville-Hotels-Walden-Spectacular-Riverfront-Cabin-On-54-Acres-Whot-Tub-Near-Luray.h22243657.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/105000000/104090000/104082100/104082014/3a15610b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/105000000/104090000/104082100/104082014/f205a55f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/105000000/104090000/104082100/104082014/e9d00149.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/105000000/104090000/104082100/104082014/e03b3dac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Shenandoah Twilight | Cozy Cabin w/ hot tub [](https://www.expedia.com/Front-Royal-Hotels-Shenandoah-Twilight-Cozy-Cabin-W-Hot-Tub.h104082014.Hotel-Information) Front Royal 9.0/10 Wonderful (2 reviews) "Shenandoah Twilight is a beautiful spot tgats beautifully appointed. I really enjoyed my time there. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wilson (Wally) W. $424 nightly $468 total Feb 24 - Feb 25 Total with taxes and fees [](https://www.expedia.com/Front-Royal-Hotels-Shenandoah-Twilight-Cozy-Cabin-W-Hot-Tub.h104082014.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/90000000/89100000/89096200/89096108/05515787.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89100000/89096200/89096108/714dfe7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89100000/89096200/89096108/4dc5543d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89100000/89096200/89096108/a53adc59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Riverfront Shenandoah Retreat – Hot Tub, Cold Plunge & Mountain Views! [](https://www.expedia.com/Woodstock-Hotels-Riverside-Heaven-FamilyRomance.h89096108.Hotel-Information) Shenandoah County 9.4/10 Exceptional (18 reviews) "Great stay for a few days over kids' Spring Break. The house is huge with tons of room. Great hiking nearby and the hot tub helped for recovery!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dwayne G. $404 nightly $415 total Feb 19 - Feb 20 Total with taxes and fees [](https://www.expedia.com/Woodstock-Hotels-Riverside-Heaven-FamilyRomance.h89096108.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/94000000/93530000/93522600/93522518/4ff9afaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/94000000/93530000/93522600/93522518/e311c93e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/94000000/93530000/93522600/93522518/fd0c3d26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, foosball, offices](https://images.trvl-media.com/lodging/94000000/93530000/93522600/93522518/76c94669.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Far View Retreat | Hot Tub + Scenic Views [](https://www.expedia.com/Front-Royal-Hotels-The-Far-View-Retreat-Hot-Tub-Scenic-Views.h93522518.Hotel-Information) Front Royal 10/10 Exceptional (15 reviews) "The cabin was spacious and well equipped. The rooms were clean and comfy. The hot tub was clean and refreshing after a long hiking day. Lovd the covered deck for watching sunrises and the deer. I heard a coyote howl early one morning." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gina H. $442 nightly $487 total Feb 24 - Feb 25 Total with taxes and fees [](https://www.expedia.com/Front-Royal-Hotels-The-Far-View-Retreat-Hot-Tub-Scenic-Views.h93522518.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/24000000/23040000/23035900/23035881/27294a86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/24000000/23040000/23035900/23035881/09a1fd28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/24000000/23040000/23035900/23035881/c1492ef4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/24000000/23040000/23035900/23035881/01d3178b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### "Sundance" Spectacular Views on 54 Acres along Shenandoah River w/ Hot Tub [](https://www.expedia.com/Rileyville-Hotels-Sundance-Spectacular-Views-On-54-Acres-Along-Shenandoah-River-W-Hot-Tub.h23035881.Hotel-Information) Rileyville 10/10 Exceptional (320 reviews) "Wonderful stay, as always. Cabin is cozy and comfortable. Views are spectacular. The hot tub is in perfect spot and perfect temp. Couldn't ask for anthing more. 1st thing I look for when we get there are the home baked cookies!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christal P. $232 nightly $268 total Feb 22 - Feb 23 Total with taxes and fees [](https://www.expedia.com/Rileyville-Hotels-Sundance-Spectacular-Views-On-54-Acres-Along-Shenandoah-River-W-Hot-Tub.h23035881.Hotel-Information) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/107000000/106850000/106847100/106847078/8a102757.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/107000000/106850000/106847100/106847078/dcc29f0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106850000/106847100/106847078/a9ab9bb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/107000000/106850000/106847100/106847078/65c860b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Amazing Grace log cabin home with 3 bedrooms, WiFi and AC in breathtaking Luray [](https://www.expedia.com/Luray-Hotels-Amazing-Grace-Log-Cabin-Home-With-3-Bedrooms.h106847078.Hotel-Information) Luray 10/10 Exceptional (52 reviews) "Great stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristen F. $478 nightly $551 total Feb 22 - Feb 23 Total with taxes and fees [](https://www.expedia.com/Luray-Hotels-Amazing-Grace-Log-Cabin-Home-With-3-Bedrooms.h106847078.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/58000000/57400000/57399100/57399073/87b38a20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/58000000/57400000/57399100/57399073/5ee98366.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/58000000/57400000/57399100/57399073/49f31f96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/58000000/57400000/57399100/57399073/a9fd5b2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cast Away Cabin [](https://www.expedia.com/Luray-Hotels-Cast-Away-Cabin.h57399073.Hotel-Information) Page County 10/10 Exceptional (26 reviews) "Wonderful and relaxing stay. Nice peaceful location. Would definitely stay here again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeremy H. $324 nightly $358 total Feb 22 - Feb 23 Total with taxes and fees [](https://www.expedia.com/Luray-Hotels-Cast-Away-Cabin.h57399073.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/71000000/70940000/70934100/70934075/231b9f0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/71000000/70940000/70934100/70934075/f9526f4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/71000000/70940000/70934100/70934075/8c61291f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, streaming services, offices](https://images.trvl-media.com/lodging/71000000/70940000/70934100/70934075/8bbcff96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### River Access Cabin w Hot Tub, Deck, Grill, & Wifi [](https://www.expedia.com/Luray-Hotels-Cabin-With-Hot-Tub.h70934075.Hotel-Information) Luray 8.6/10 Excellent (24 reviews) "As it is described. Clean and peaceful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anna A. $272 nightly $300 total Feb 23 - Feb 24 Total with taxes and fees [](https://www.expedia.com/Luray-Hotels-Cabin-With-Hot-Tub.h70934075.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/73000000/72620000/72615800/72615768/9bd8f097.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player](https://images.trvl-media.com/lodging/73000000/72620000/72615800/72615768/36d96e2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/73000000/72620000/72615800/72615768/324a1cb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/73000000/72620000/72615800/72615768/5d06ee21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Shenandoah Mountain Cabin [](https://www.expedia.com/Rileyville-Hotels-Shenandoah-Mountain-Cabin.h72615768.Hotel-Information) Rileyville 10/10 Exceptional (20 reviews) "Absolutely beautiful property. The house was cozy and very clean. The kitchen was perfect and the hot tub well maintained. Will 100% be back to this property. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ashley T. $389 nightly $431 total Feb 19 - Feb 20 Total with taxes and fees [](https://www.expedia.com/Rileyville-Hotels-Shenandoah-Mountain-Cabin.h72615768.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/84000000/83550000/83542600/83542571/902dd466.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83550000/83542600/83542571/159749b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83550000/83542600/83542571/fb69b272.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/84000000/83550000/83542600/83542571/c6dcd95e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities [](https://www.expedia.com/Luray-Hotels-Dog-Friendly-Shenandoah-Views-Wifi.h83542571.Hotel-Information) Luray 9.6/10 Exceptional (71 reviews) "Very large yard for our dogs to run & play. Convenient firewood available on site (for a fee). Provided great board games to keep us entertained. Very comfortable stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mimosa L. $274 nightly $314 total Feb 19 - Feb 20 Total with taxes and fees [](https://www.expedia.com/Luray-Hotels-Dog-Friendly-Shenandoah-Views-Wifi.h83542571.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19980000/19978300/19978224/3cd13b81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books, stereo, offices](https://images.trvl-media.com/lodging/20000000/19980000/19978300/19978224/540472e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/20000000/19980000/19978300/19978224/9c1f7ef4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/20000000/19980000/19978300/19978224/431a8bf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary [](https://www.expedia.com/Viewtown-Hotels-Surrounded-By-Majestic-Trees-Hilltop-Is-Located-In-The-Piedmont-Of-Virginia.h19978224.Hotel-Information) Amissville 9.8/10 Exceptional (89 reviews) "Hilltop Hideaway is a very charming house out in the middle of beautiful country by itself. We only stayed one night but we were very impressed with how clean the house is." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa S. $401 nightly $422 total Feb 19 - Feb 20 Total with taxes and fees [](https://www.expedia.com/Viewtown-Hotels-Surrounded-By-Majestic-Trees-Hilltop-Is-Located-In-The-Piedmont-Of-Virginia.h19978224.Hotel-Information) ![Fireplace, DVD player](https://images.trvl-media.com/lodging/37000000/36850000/36842400/36842363/37c391be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/37000000/36850000/36842400/36842363/1ddc369e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/37000000/36850000/36842400/36842363/30fa4206.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/37000000/36850000/36842400/36842363/92a0bb64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Clouds Mountain Cabin [](https://www.expedia.com/Rileyville-Hotels-Clouds-Mountain-Cabin.h36842363.Hotel-Information) Rileyville 9.4/10 Exceptional (16 reviews) "We had a very quiet nice stay it was nice to have the woods where we could walk the dogs. The drive up was a little difficult even with four wheel drive but definitely worth the view " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica S. $389 nightly $431 total Feb 19 - Feb 20 Total with taxes and fees [](https://www.expedia.com/Rileyville-Hotels-Clouds-Mountain-Cabin.h36842363.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/32000000/31180000/31175700/31175686/e6d871fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, stereo](https://images.trvl-media.com/lodging/32000000/31180000/31175700/31175686/d18c2b7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, stereo](https://images.trvl-media.com/lodging/32000000/31180000/31175700/31175686/4b193a83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, stereo](https://images.trvl-media.com/lodging/32000000/31180000/31175700/31175686/70601898.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Reel It In Cabin [](https://www.expedia.com/Luray-Hotels-Reel-It-In-Cabin.h31175686.Hotel-Information) Page County 9.6/10 Exceptional (50 reviews) "Beautifully maintained private cabin..Owners were so nice in helping to assist our family getaway. Definitely would recommend... looking forward to planning our next trip." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leo P. $325 nightly $360 total Feb 23 - Feb 24 Total with taxes and fees [](https://www.expedia.com/Luray-Hotels-Reel-It-In-Cabin.h31175686.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/90000000/89800000/89792300/89792293/b8ee4a7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/90000000/89800000/89792300/89792293/b47a597b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/90000000/89800000/89792300/89792293/3bbd1dbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/90000000/89800000/89792300/89792293/0344fe88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spring Retreat! Hot tub, Bar, Game room, Grill & 10 mins to Skyline Drive [](https://www.expedia.com/Front-Royal-Hotels-Spacious-Home-Near-Natl-Park.h89792293.Hotel-Information) Front Royal 9.8/10 Exceptional (34 reviews) "Great place to stay. Will go back! Thanks " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gareth E. $393 nightly $433 total Feb 19 - Feb 20 Total with taxes and fees [](https://www.expedia.com/Front-Royal-Hotels-Spacious-Home-Near-Natl-Park.h89792293.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/122000000/121770000/121766400/121766304/e4739be1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121770000/121766400/121766304/33aedc3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/122000000/121770000/121766400/121766304/234bd7f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/122000000/121770000/121766400/121766304/ccd121a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury tiny home farm stay on historic property with hot tub in Stephens City [](https://www.expedia.com/Stephens-City-Hotels-Luxury-Tiny-Home-Farm-Stay-On-Historic-Property-With-Hot-Tub-In-Stephens-City.h121766304.Hotel-Information) Stephens City 10/10 Exceptional (1 review) "Fresh bread, farm eggs, an amazing host! What a perfect place to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris F. $151 nightly $164 total Feb 23 - Feb 24 Total with taxes and fees [](https://www.expedia.com/Stephens-City-Hotels-Luxury-Tiny-Home-Farm-Stay-On-Historic-Property-With-Hot-Tub-In-Stephens-City.h121766304.Hotel-Information) 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. [View all properties](https://expedia.com/Hotel-Search?startDate=2026-03-04&endDate=2026-03-05®ionId=553248635975865285&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](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=VR_SPRING_PROMO_553248635975865285) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.com/Hotel-Search?destination=Chester+Gap%2C+Virginia%2C+United+States+of+America®ionId=553248635975865285&latLong=38.853485%2C-78.134962&adults=2&startDate=2026-05-19&d1=2026-05-19&endDate=2026-05-22&d2=2026-05-22&lodging=CABIN) Apartments [](https://www.expedia.com/Hotel-Search?destination=Chester+Gap%2C+Virginia%2C+United+States+of+America®ionId=553248635975865285&latLong=38.853485%2C-78.134962&adults=2&startDate=2026-05-19&d1=2026-05-19&endDate=2026-05-22&d2=2026-05-22&lodging=APARTMENT) Villas [](https://www.expedia.com/Hotel-Search?destination=Chester+Gap%2C+Virginia%2C+United+States+of+America®ionId=553248635975865285&latLong=38.853485%2C-78.134962&adults=2&startDate=2026-05-19&d1=2026-05-19&endDate=2026-05-22&d2=2026-05-22&lodging=VILLA) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Chester+Gap%2C+Virginia%2C+United+States+of+America®ionId=553248635975865285&latLong=38.853485%2C-78.134962&adults=2&startDate=2026-05-19&d1=2026-05-19&endDate=2026-05-22&d2=2026-05-22&lodging=VACATION_HOME) Cottages [](https://www.expedia.com/Hotel-Search?destination=Chester+Gap%2C+Virginia%2C+United+States+of+America®ionId=553248635975865285&latLong=38.853485%2C-78.134962&adults=2&startDate=2026-05-19&d1=2026-05-19&endDate=2026-05-22&d2=2026-05-22&lodging=COTTAGE) Chalets [](https://www.expedia.com/Hotel-Search?destination=Chester+Gap%2C+Virginia%2C+United+States+of+America®ionId=553248635975865285&latLong=38.853485%2C-78.134962&adults=2&startDate=2026-05-19&d1=2026-05-19&endDate=2026-05-22&d2=2026-05-22&lodging=CHALET) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChester-Gap-Vacation-Rentals.d553248635975865285.Travel-Guide-VacationRentals)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Gap-Vacation-Rentals.d553248635975865285.Travel-Guide-VacationRentals) ## Top Chester Gap Hotel Reviews ![DoubleTree by Hilton Front Royal Blue Ridge Shadows](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/204cbf3a_y.jpg) ### DoubleTree by Hilton Front Royal Blue Ridge Shadows 10/10 Excellent "Professional staff. Hotel was clean and fresh." [](https://expedia.com/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.Hotel-Information) ![Ramada by Wyndham Strasburg/Shenandoah Valley](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/08da8378_y.jpg) ### Ramada by Wyndham Strasburg/Shenandoah Valley 10/10 Excellent "The facilities were great and the customer service was excellent. We also really appreciated the good complimentary breakfast." [](https://expedia.com/Winchester-Hotels-Ramada-By-Wyndham-Strasburg.h1246311.Hotel-Information) ![Country Inn & Suites by Radisson, Winchester, VA](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/d0690cde_y.jpg) ### Country Inn & Suites by Radisson, Winchester, VA 10/10 Excellent "the room was very comfortable and the hot breakfast was great. the hotel maintenance guy, Steve, was very helpful in offering to jumpstart our car the next morning when it wouldn't start. the only issue was that the TV was set in Spanish and no one could get it reset to be in English." [](https://expedia.com/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) ![Comfort Inn & Suites Winchester](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/cf4c2663_y.jpg) ### Comfort Inn & Suites Winchester 10/10 Excellent "Very friendly staff. Quick easy check in. Comfortable, clean room and a nice breakfast for a great price!" [](https://expedia.com/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information) ![Star view cabin-Riverfront ](https://images.trvl-media.com/lodging/31000000/30790000/30788500/30788475/2cb5e40f_y.jpg) ### Star view cabin-Riverfront 10/10 Excellent "The host was exceptional and quick to respond to questions. Loved the cabin, it was in great condition, clean and very nicely set up. The views to the river and the mountains beyond were breath taking with the snow and ice from a recent storm." [](https://expedia.com/Rileyville-Hotels-Star-View-Cabin-Riverfront.h30788475.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) ### "Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA. 10/10 Excellent "excellent location. Awesome floor plan for this one bedroom one bath cabin. Was very clean and had a perfect view of Shenandoah River.Bed was vm very comfy, large full bathroom & great four person hot tub on the front porch overlooking a great view of the river. Even with it being 90 at night we enjoyed the hot temps of the hot tub.Can’t wait to come back in the spring when everything is green. Highly recommend this cabin. The host was super on communication A" [](https://expedia.com/Rileyville-Hotels-Solitude-Spectacular-1-BR-Cabin-W-Hot-Tub-Near-Luray.h22255620.Hotel-Information) ![Holiday Inn Express Winchester South-Stephens City by IHG](https://images.trvl-media.com/lodging/1000000/40000/34400/34394/ef7d5b18_y.jpg) ### Holiday Inn Express Winchester South-Stephens City by IHG 10/10 Excellent "The room was spotless, staff is excellent. Well, recommend the stay to everyone I know" [](https://expedia.com/Winchester-Hotels-Holiday-Inn-Express-Winchester-South-Stephens-City.h34394.Hotel-Information) ![Magical Riverfront Retreat in Luray – Cozy Getaway with Stunning Views!](https://images.trvl-media.com/lodging/68000000/67280000/67276000/67275918/1986cf55_y.jpg) ### Magical Riverfront Retreat in Luray – Cozy Getaway with Stunning Views! 10/10 Excellent "The property is in a very nice setting and kept very well. Great views and super fire pit! " [](https://expedia.com/Luray-Hotels-Cozy-Riverfront-Cabin-On-The-Shenandoah.h67275918.Hotel-Information) ![Baymont by Wyndham Front Royal Near Shenandoah National Park](https://images.trvl-media.com/lodging/1000000/20000/10600/10535/071235b5_y.jpg) ### Baymont by Wyndham Front Royal Near Shenandoah National Park 10/10 Excellent "Nice staff " [](https://expedia.com/Winchester-Hotels-Baymont-By-Wyndham-Front-Royal-Near-Shenandoah-National-Park.h10535.Hotel-Information) ## Find out more about Chester Gap **Everything you need to know about Chester Gap vacation rentals** Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chester Gap vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on. There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chester Gap vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. **Chester Gap vacation rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Chester Gap. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chester Gap in high season. Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $223 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals! **How to find incredible deals on Chester Gap rentals** At Expedia, we put the best Chester Gap vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. To find some top Chester Gap rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chester Gap vacation. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester Gap. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. ## Explore a world of travel with Expedia - Trending destinations on Expedia.com - All accommodation types in Chester Gap ### Trending destinations on Expedia.com - [Destin Vacation Rentals ](https://www.expedia.com/Destin-Vacation-Rentals.d6906.Travel-Guide-VacationRentals) - [Panama City Vacation Rentals ](https://www.expedia.com/Panama-City-Beach-Vacation-Rentals.d8021.Travel-Guide-VacationRentals) - [Hilton Head Vacation Rentals ](https://www.expedia.com/Hilton-Head-Island-Vacation-Rentals.d601684.Travel-Guide-VacationRentals) - [Gulf Shores Vacation Rentals ](https://www.expedia.com/Gulf-Shores-Vacation-Rentals.d603078.Travel-Guide-VacationRentals) - [Key West Vacation Rentals ](https://www.expedia.com/Key-West-Vacation-Rentals.d1187.Travel-Guide-VacationRentals) - [Gatlinburg Vacation Rentals ](https://www.expedia.com/Gatlinburg-Vacation-Rentals.d7474.Travel-Guide-VacationRentals) - 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[Cabin Rentals in Chester Gap ](https://expedia.com/Chester-Gap-Cabins.d553248635975865285-aaCabins.Travel-Guide-Accommodation) - [Vacation Homes in Chester Gap ](https://expedia.com/Chester-Gap-Private-Vacation-Homes.d553248635975865285-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Cottages in Chester Gap ](https://expedia.com/Chester-Gap-Cottages.d553248635975865285-aaCottages.Travel-Guide-Accommodation) - [Apartments in Chester Gap ](https://expedia.com/Chester-Gap-Apartments.d553248635975865285-aaApartments.Travel-Guide-Accommodation) - [Farmstay in Chester Gap ](https://expedia.com/Chester-Gap-Agritourism.d553248635975865285-aaAgritourism.Travel-Guide-Accommodation) - [Motels in Chester Gap ](https://expedia.com/Chester-Gap-Motels.d553248635975865285-aaMotels.Travel-Guide-Accommodation) - [Chalets in Chester Gap ](https://expedia.com/Chester-Gap-Chalets.d553248635975865285-aaChalets.Travel-Guide-Accommodation) - [Guest Houses in Chester Gap ](https://expedia.com/Chester-Gap-Guest-Houses.d553248635975865285-aaGuestHouses.Travel-Guide-Accommodation) - [Lodges in Chester Gap ](https://expedia.com/Chester-Gap-Lodges.d553248635975865285-aaLodges.Travel-Guide-Accommodation) - [Villas in Chester Gap ](https://expedia.com/Chester-Gap-Villas.d553248635975865285-aaVillas.Travel-Guide-Accommodation) - [B&B in Chester Gap ](https://expedia.com/Chester-Gap-Bed-And-Breakfast.d553248635975865285-aaBedAndBreakfast.Travel-Guide-Accommodation) - [RV Parks in Chester Gap ](https://expedia.com/Chester-Gap-RV-Parks.d553248635975865285-aaRVParks.Travel-Guide-Accommodation) - [Inns in Chester Gap ](https://expedia.com/Chester-Gap-Inns.d553248635975865285-aaInns.Travel-Guide-Accommodation) - [Condo Rentals in Chester Gap ](https://expedia.com/Chester-Gap-Condos.d553248635975865285-aaCondos.Travel-Guide-Accommodation) ## Frequently asked questions ### Are there vacation rentals in Chester Gap? ### What are some of the best vacation rentals in Chester Gap? ### How many vacation rentals will I find in Chester Gap? ### What can I see and do in Chester Gap? ### What are vacation rentals like in Chester Gap? ![](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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