Title: Chester Gap Cottages from CA $516 | 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 # Search Chester Gap Cottage Rentals from CA $516 ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](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) ![](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&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635975865285&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chester Gap Cottages ![Outdoor spa tub](https://images.trvl-media.com/lodging/79000000/78100000/78093100/78093042/63526894.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/79000000/78100000/78093100/78093042/1e065e7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78100000/78093100/78093042/6d4d454a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/79000000/78100000/78093100/78093042/2f7695a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Riverfront! Shenandoah River! Sleeps 4! New Hot Tub Front Royal 9.8/10 Exceptional (13) "What a beautiful little house!! And can’t beat the magnificent view of the river! " CA $348 CA $516 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Front-Royal-Hotels-Stunning-Riverfront-Shenandoah-River-Sleeps-4.h78093042.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/a69388d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/45164b22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/c2c2b573.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/92092e5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Vue - Mountain top hot tub overlooking the Shenandoah River Front Royal 9.8/10 Exceptional (7) "Love the view and beautiful appointed decor throughout the home…" CA $256 CA $573 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Front-Royal-Hotels-The-Vue-Mountain-Top-Hot-Tub-Overlooking-The-Shenandoah-River.h107613898.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/9a2bb6ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/4c56e3e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/b8a5d193.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/dbdd487f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### "Prima BnB" a Superb 4-bedroom cottage on the mountain near Front Royal Front Royal CA $326 CA $720 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Front-Royal-Hotels-Prima-A-Superb-4-Bedroom-Cottage-On-The-Mountain-Near-Front-Royal.h119496330.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=2025-10-24&endDate=2025-10-25®ionId=553248635975865285&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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-Cottages.d553248635975865285-aaCottages.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Gap-Cottages.d553248635975865285-aaCottages.Travel-Guide-Accommodation) ## Top Chester Gap Hotel Reviews ![Fairfield Inn & Suites Strasburg Shenandoah Valley](//images.trvl-media.com/lodging/3000000/2240000/2230900/2230885/2df64736_y.jpg) ### Fairfield Inn & Suites Strasburg Shenandoah Valley 10/10 Excellent "Staff was very nice, check in was a breeze. Room was clean and comfortable, nice area Restaurants nearby" [](https://expedia.ca/Winchester-Hotels-Fairfield-Inn-Suites-Strasburg-Shenandoah-Valley.h2230885.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 "Perfect stop over on our road trip. Clean with friendly staff. Breakfast was great with waffle machines!" [](https://expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) ![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) ![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) ![Falling Leaf Cabin - Rustic Charm With Modern Decor!](//images.trvl-media.com/lodging/34000000/33750000/33748300/33748224/e001c092_y.jpg) ### Falling Leaf Cabin - Rustic Charm With Modern Decor! 10/10 Excellent "Wonderful time. Always a peaceful, quiet respite! 3rd time staying here over the last few years. Andrea is a great host." [](https://expedia.ca/Rileyville-Hotels-Falling-Leaf-Cabin-Secluded-With-Mountain-View.h33748224.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) ## Find out more about Chester Gap ## Chester Gap Cottages information | Number of reviews | 19 | | --- | --- | | Accommodation | 53 Cottages | | Lowest Price | CA $516 | | Highest Price | CA $720 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [Ashville Hotels](https://www.expedia.ca/Ashville-Hotels.d553248635975846883.Travel-Guide-Hotels) - [Luxury Hotels in Bentonville](https://www.expedia.ca/Bentonville-Hotels-Luxury-Hotel.0-0-d6353683-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Bentonville Hotels](https://www.expedia.ca/Bentonville-Hotels.d6353683.Travel-Guide-Hotels) - 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[Book Cottages in Chester Gap on Expedia.com](https://www.expedia.com/Chester-Gap-Cottages.d553248635975865285-aaCottages.Travel-Guide-Accommodation)