Title: Chester Gap Vacation Home Rentals from CA $289: Search Top Private Vacation Homes for Rent | Expedia.ca [Chester Gap Travel Guide](https://expedia.ca/Chester-Gap.dx553248635975865285)[Hotels in Chester Gap](https://expedia.ca/Chester-Gap-Hotels.d553248635975865285.Travel-Guide-Hotels)[Vacation Rentals in Chester Gap](https://expedia.ca/Chester-Gap-Vacation-Rentals.d553248635975865285.Travel-Guide-VacationRentals)[Chester Gap Car Rentals](https://expedia.ca/Car-Rentals-In-Chester-Gap.d553248635975865285.Car-Rental-Guide)[Chester Gap Vacation Packages](https://expedia.ca/Chester-Gap.d553248635975865285.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/a636e33b71dd87047fd3a46ed8933b8f.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Brian V. Rowe # Chester Gap Vacation Rentals ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635975865285&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=553248635975865285&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635975865285&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=553248635975865285&startDate=2026-01-30&endDate=2026-02-01&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chester Gap Vacation Homes ![Exterior detail](https://images.trvl-media.com/lodging/113000000/112770000/112761300/112761217/3fb8f14c_edited_6688.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/113000000/112770000/112761300/112761217/w1290h2284x0y0-8ada8d72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112770000/112761300/112761217/w1290h982x0y0-a74e1c0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels, soap, shampoo](https://images.trvl-media.com/lodging/113000000/112770000/112761300/112761217/w1290h1720x0y7-db264944.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 1-bedroom house with WiFi, AC in Pleasant Rixeyville, VA on 13 acres! Rixeyville 10/10 Exceptional (2) "Great little place. Perfect for one or two travelers.Super nice hosts. Would highly recommend." CA $124 CA $316 total includes taxes & fees Oct 11 - Oct 12 [](https://www.expedia.ca/Rixeyville-Hotels-Charming-1-Bedroom-House-With-WiFi.h112761217.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118930000/118929700/118929649/1520d4f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118930000/118929700/118929649/88d4dc47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/119000000/118930000/118929700/118929649/cad5963c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118930000/118929700/118929649/928d407e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain View Bungalow in Front Royal Front Royal 10/10 Exceptional (4) "Property was just what we were looking for " CA $188 CA $307 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Front-Royal-Hotels-Mountain-View-Bungalow-In-Front-Royal.h118929649.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/121000000/120880000/120875700/120875632/a0fc17d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi](https://images.trvl-media.com/lodging/121000000/120880000/120875700/120875632/ba35ee79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/121000000/120880000/120875700/120875632/91e77a30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/121000000/120880000/120875700/120875632/4a222dc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain Summit Views Hot Tub-Fire Pit-BBQ, Pets Page County CA $194 CA $428 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Rileyville-Hotels-Mountain-Summit-Views-Hot-Tub-Fire-Pit-BBQ.h120875632.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115820000/115816400/115816319/72d53a97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/115820000/115816400/115816319/9d7eeb9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/116000000/115820000/115816400/115816319/a89dd629.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/116000000/115820000/115816400/115816319/f6dfde7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jacuzzi • Gym • Deck + Near VA Wineries Linden 10/10 Exceptional (1) "Had a lovely stay. " CA $256 CA $627 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Linden-Hotels-3BR-Family-Home-W-Yard-5-Mi-To-Wineries.h115816319.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119610000/119607400/119607329/aece8443.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi](https://images.trvl-media.com/lodging/120000000/119610000/119607400/119607329/7d28e89f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119610000/119607400/119607329/5c5701ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119610000/119607400/119607329/aaca8b6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bear Ridge Cabin-Views & Hot tub Page County CA $223 CA $467 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Rileyville-Hotels-Bear-Ridge-Cabin-Views-Hot-Tub.h119607329.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/61000000/60280000/60275500/60275491/a448a4eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/61000000/60280000/60275500/60275491/7966de65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/61000000/60280000/60275500/60275491/73acc693.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/61000000/60280000/60275500/60275491/fcd07d5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Cottage w Hot Tub, Fire Pit, WiFi & Sunroom! Front Royal 9.0/10 Wonderful (26) "Everything was as described. We had a lovely weekend relaxing under the stars in the hot tub and spending time with family in the Shenandoah Valley. We can't wait to come back to this oasis!" CA $236 CA $424 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Front-Royal-Hotels-Hot-Tub.h60275491.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/120000000/119580000/119575200/119575138/7767ff33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119580000/119575200/119575138/ed03a07f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119580000/119575200/119575138/6ca1da62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/120000000/119580000/119575200/119575138/4f193834.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Screened Porch w/Swing, Fire Pit, Grill & Deck Luray CA $221 CA $434 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Luray-Hotels-Screened-Porch-WSwing.h119575138.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/90000000/89670000/89661800/89661737/447b9317.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/90000000/89670000/89661800/89661737/3d01944d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89670000/89661800/89661737/8f100ddb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/90000000/89670000/89661800/89661737/bc0d2448.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Completely Private Suite in Historic Colonial House right beside from The Inn! Washington 10/10 Exceptional (16) "an excellent option if dining at the INN" CA $169 CA $289 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Washington-Hotels-Across-The-Inn-Completely-Private-Half-House-With-Kitchen.h89661737.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106120000/106119000/106118941/w1199h800x1y1-0ba358b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/107000000/106120000/106119000/106118941/w1199h800x1y1-faf2077f.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/107000000/106120000/106119000/106118941/w1199h800x1y1-20a50c5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106120000/106119000/106118941/aa1c40d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious & Fun Family Oasis ~ Games ~ Hot Tub ~ View Rileyville 10/10 Exceptional (4) "Very welcoming home. It was a great place to relax and enjoy time with our family. It served as a perfect “base camp” for hikes at Shenandoah National Park. The home owner has provided additional amenities (soap, shampoo, k-cups, games,…) which was an added bonus. We really enjoyed our stay." CA $312 CA $683 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Rileyville-Hotels-Spacious-Fun-Family-Oasis-Games-Hot-Tub-View.h106118941.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/90000000/89800000/89794800/89794757/15fd4469.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89800000/89794800/89794757/8e6ba5b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/90000000/89800000/89794800/89794757/3bc90753.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89800000/89794800/89794757/bc1a175e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Newly renovated Farm cottage with Mountain views Strasburg 10/10 Exceptional (36) "Very clean cottage with well-stocked kitchen with a great outdoors area for grilling and hanging out. Quiet relaxing location way up off the road. The hosts were unobtrusive but available. We have already recommended this cottage to our immediate family for future stays. " CA $223 CA $443 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Strasburg-Hotels-Newly-Renovated-Farm-Cottage-With-Mountain-Views.h89794757.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/118000000/117740000/117735000/117734997/w2999h2002x1y1-de179e9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117740000/117735000/117734997/58d98b30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/118000000/117740000/117735000/117734997/w3000h2002x0y1-874ebd45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/118000000/117740000/117735000/117734997/w2998h2002x1y1-e4dac9a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Welcome to the Ladybug Retreat! Boyce 10/10 Exceptional (1) "This home is lovely and the host has thought of everything. We will definitely stay here again. " CA $254 CA $566 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Paris-Hotels-Welcome-To-The-Ladybug-Retreat.h117734997.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106390000/106383400/106383324/45f17d6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/107000000/106390000/106383400/106383324/a9c7237d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/107000000/106390000/106383400/106383324/52f27a00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/107000000/106390000/106383400/106383324/6f531793.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dream Dome - Romantic Retreat + Wifi A/C + Hot Tub Luray 10/10 Exceptional (5) "This was a great place to stay for a change of setting. So much more fun than a hotel room. The hot tub was a nice extra and bed was super comfortable. Nice to be able to have a cup of coffee and sit outside at picnic table. Great place!" [](https://www.expedia.ca/Luray-Hotels-Dream-Dome-Romantic-Retreat-Wifi-AC-Hot-Tub.h106383324.Hotel-Information) ![Fireplace, DVD player](https://images.trvl-media.com/lodging/37000000/36850000/36842400/36842363/9be3191b.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) ![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) ### Clouds Mountain Cabin Rileyville 9.4/10 Exceptional (15) "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 " CA $290 CA $547 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Rileyville-Hotels-Clouds-Mountain-Cabin.h36842363.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) ![TV, fireplace, stereo](https://images.trvl-media.com/lodging/28000000/27480000/27477100/27477055/cb868b5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi](https://images.trvl-media.com/lodging/28000000/27480000/27477100/27477055/ffb104c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, dishwasher, toaster, cookware/dishes/utensils](https://images.trvl-media.com/lodging/28000000/27480000/27477100/27477055/41c4b581.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stepping Stone Cabin Page County 9.8/10 Exceptional (48) "awesome stay we will love to go again" CA $274 CA $470 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Luray-Hotels-Stepping-Stone-Cabin.h27477055.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) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19980000/19978300/19978224/41352bf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/20000000/19980000/19978300/19978224/d8c4682d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/20000000/19980000/19978300/19978224/18816cd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary Amissville 9.8/10 Exceptional (87) "Great place that works well for Rixey Manor weddings " CA $286 CA $577 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Viewtown-Hotels-Surrounded-By-Majestic-Trees-Hilltop-Is-Located-In-The-Piedmont-Of-Virginia.h19978224.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/112000000/112000000/111990300/111990276/e139efbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/112000000/111990300/111990276/76a4647a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/112000000/111990300/111990276/88dda1a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/112000000/112000000/111990300/111990276/d0fdda42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 2-bedroom condo in charming Stephens City Stephens City 10/10 Exceptional (1) "This was the perfect location for our little get away. We had Easter lunch, played games, and stayed in a very clean nice place!!" CA $234 CA $325 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Stephens-City-Hotels-Cozy-2-Bedroom-Condo-In-Charming-Stephens-City.h111990276.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/110000000/109880000/109878800/109878773/73389cdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, foosball, table tennis](https://images.trvl-media.com/lodging/110000000/109880000/109878800/109878773/7e2afb22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109880000/109878800/109878773/e77f0b8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109880000/109878800/109878773/4dc2f433.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hidden Hollow 3BD Cabin - Hot Tub+ Wifi+ Game Room Luray 10/10 Exceptional (1) "Very nice place. As advertised. Great for families. Can easily fit 2 families. Very quiet, great location. Seems newly renovated which is a plus so everything is updated. Great communication with owner. The separate game room hacienda is a real plus and a lot of fun. A couple of minor new place kinks to be worked out; for example no hangers in closets, and need to make sure the hottub is ready to use. Otherwise, a good find and would happily stay again. " CA $439 CA $669 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Luray-Hotels-Hidden-Hollow-3BD-Cabin-Hot-Tub-Wifi-Game-Room.h109878773.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/114000000/113940000/113933300/113933293/25a6efcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, offices, computer monitors](https://images.trvl-media.com/lodging/114000000/113940000/113933300/113933293/563df015.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113940000/113933300/113933293/ea0185a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, offices, computer monitors](https://images.trvl-media.com/lodging/114000000/113940000/113933300/113933293/a2c39a40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Apple Mountain House Front Royal 9.6/10 Exceptional (4) "Amazing place to relax." CA $264 CA $640 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Front-Royal-Hotels-The-Apple-Mountain-House.h113933293.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/73000000/72620000/72615800/72615768/324a1cb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/73000000/72620000/72615800/72615768/de8d068b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/73000000/72620000/72615800/72615768/acc3e895.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/efb0dc0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Shenandoah Mountain Cabin Rileyville 10/10 Exceptional (16) "This place is amazing! So clean and comfortable. Drive up to the cabin is very bumpy but so very worth it. " CA $277 CA $522 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Rileyville-Hotels-Shenandoah-Mountain-Cabin.h72615768.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106670000/106661600/106661557/9943899e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/107000000/106670000/106661600/106661557/5f8b6abe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/107000000/106670000/106661600/106661557/db9fd57a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/107000000/106670000/106661600/106661557/994e7769.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Zen Dome - Romantic Retreat + Wifi A/C + Hot Tub Luray CA $403 CA $608 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Luray-Hotels-Zen-Dome-Romantic-Retreat-Wifi-AC-Hot-Tub.h106661557.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.ca/Hotel-Search?startDate=2025-10-22&endDate=2025-10-23®ionId=553248635975865285&adults=2&lodging=VACATION_HOME&sort=RECOMMENDED&openPlayBack=true) ![](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.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChester-Gap-Private-Vacation-Homes.d553248635975865285-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Gap-Private-Vacation-Homes.d553248635975865285-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Chester Gap Hotel Reviews ![Ramada by Wyndham Strasburg/Shenandoah Valley](//images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/08da8378_y.jpg) ### Ramada by Wyndham Strasburg/Shenandoah Valley 10/10 Excellent "The room was perfect for a one night stay while passing through the area. The room was clean, the bed was comfortable and the location was convenient. Check in was fast and easy." [](https://expedia.ca/Winchester-Hotels-Ramada-By-Wyndham-Strasburg.h1246311.Hotel-Information) ![Country Inn & Suites by Radisson, Winchester, VA](//images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/d0690cde_y.jpg) ### Country Inn & Suites by Radisson, Winchester, VA 10/10 Excellent "Great stay. Pleasant staff. Price was good. Quick, easy check in. Room clean and pet free (as requested). Breakfast was biscuits and gravy, waffles, danishes but no eggs. Would stay again if in area. " [](https://expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) ![Hampton Inn Front Royal](//images.trvl-media.com/lodging/1000000/900000/892600/892585/75c26333_y.jpg) ### Hampton Inn Front Royal 10/10 Excellent "Friendly staff and good breakfast. " [](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.Hotel-Information) ![Adorable river front cabin ,with hot tub on the River](//images.trvl-media.com/lodging/100000000/99530000/99521700/99521601/84599548_y.jpg) ### Adorable river front cabin ,with hot tub on the River 10/10 Excellent "Excellent " [](https://expedia.ca/Luray-Hotels-The-Blue-Heron-Cabin-On-The-River.h99521601.Hotel-Information) ![Comfort Inn & Suites Winchester](//images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/cf4c2663_y.jpg) ### Comfort Inn & Suites Winchester 10/10 Excellent "Clean room and spacious" [](https://expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information) ![DoubleTree by Hilton Front Royal Blue Ridge Shadows](//images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/204cbf3a_y.jpg) ### DoubleTree by Hilton Front Royal Blue Ridge Shadows 10/10 Excellent "Everything was what I expected friendly staff. Everything was clean. Everything worked Pleasant property decent attached restaurant" [](https://expedia.ca/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.Hotel-Information) ![Holiday Inn Express Winchester South-Stephens City by IHG](//images.trvl-media.com/lodging/1000000/40000/34400/34394/4d102079_y.jpg) ### Holiday Inn Express Winchester South-Stephens City by IHG 10/10 Excellent "always a pleasure to stay here. checkin and out is flawless. staff are very friendly." [](https://expedia.ca/Winchester-Hotels-Holiday-Inn-Express-Winchester-South-Stephens-City.h34394.Hotel-Information) ![TownePlace Suites by Marriott Front Royal](//images.trvl-media.com/lodging/37000000/36350000/36342700/36342604/0776aa15_y.jpg) ### TownePlace Suites by Marriott Front Royal 10/10 Excellent "Has everything " [](https://expedia.ca/Winchester-Hotels-TownePlace-Suites-By-Marriott-Front-Royal.h36342604.Hotel-Information) ![Super 8 by Wyndham Front Royal](//images.trvl-media.com/lodging/1000000/860000/855600/855557/10b5cc1e_y.jpg) ### Super 8 by Wyndham Front Royal 10/10 Excellent "Area " [](https://expedia.ca/Winchester-Hotels-Super-8-By-Wyndham-Front-Royal.h855557.Hotel-Information) ## Find out more about Chester Gap ## Chester Gap Vacation Homes information | Number of reviews | 211 | | --- | --- | | Accommodation | 156 Vacation Homes | | Lowest Price | CA $289 | | Highest Price | CA $683 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - 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