Title: Chester Gap Cottages from CA $305 | 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) ![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__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 [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=553248635975865285&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=553248635975865285&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=553248635975865285&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 26 - Jun 28](https://www.expedia.ca/Hotel-Search?regionId=553248635975865285&startDate=2026-06-26&endDate=2026-06-28&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 cottages ![Terrace/patio](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/7f22680b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/0c0a82ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/120000000/119500000/119496400/119496330/212d2c5a.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 [](https://www.expedia.ca/Front-Royal-Hotels-Prima-A-Superb-4-Bedroom-Cottage-On-The-Mountain-Near-Front-Royal.h119496330.Hotel-Information) Front Royal 10/10 Exceptional (5 reviews) "My family and I had a wonderful stay! The property and surrounding views are beautiful. The house was very clean and the host was very responsive when I had a question or two to ask. I highly recommend staying here!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jay L. CA $166 CA $518 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Front-Royal-Hotels-Prima-A-Superb-4-Bedroom-Cottage-On-The-Mountain-Near-Front-Royal.h119496330.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/52000000/51510000/51509100/51509047/4a296327.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/52000000/51510000/51509100/51509047/4383aa6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/52000000/51510000/51509100/51509047/ea22e17f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/52000000/51510000/51509100/51509047/9a866bf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View [](https://www.expedia.ca/Front-Royal-Hotels-Country-Cottage-Beside-Stocked-Pond-On-40-Acres-And-Blue-Ridge-Mountain-View.h51509047.Hotel-Information) Front Royal 9.6/10 Exceptional (17 reviews) "Nice place, comfortable bed. Close to hiking in the area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jake M. CA $203 CA $305 total includes taxes & fees Mar 18 - Mar 19 [](https://www.expedia.ca/Front-Royal-Hotels-Country-Cottage-Beside-Stocked-Pond-On-40-Acres-And-Blue-Ridge-Mountain-View.h51509047.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/f7d693d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/f8332737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/d80b6458.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107620000/107613900/107613898/3d395fb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Vue - Mountain Top hot tub overlooking the Shenandoah River [](https://www.expedia.ca/Front-Royal-Hotels-The-Vue-Mountain-Top-Hot-Tub-Overlooking-The-Shenandoah-River.h107613898.Hotel-Information) Front Royal 10/10 Exceptional (16 reviews) "We had a phenomenal stay! The view was absolutely breathtaking, and the house was well-kept and comfortable. We’re already talking about our next trip!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dan P. CA $230 CA $598 total includes taxes & fees Mar 15 - Mar 16 [](https://www.expedia.ca/Front-Royal-Hotels-The-Vue-Mountain-Top-Hot-Tub-Overlooking-The-Shenandoah-River.h107613898.Hotel-Information) ![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) ![Dining](https://images.trvl-media.com/lodging/79000000/78100000/78093100/78093042/2f7695a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/79000000/78100000/78093100/78093042/ea22ac13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/79000000/78100000/78093100/78093042/197f6c5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Riverfront! Shenandoah River! Sleeps 4! New Hot Tub [](https://www.expedia.ca/Front-Royal-Hotels-Stunning-Riverfront-Shenandoah-River-Sleeps-4.h78093042.Hotel-Information) Front Royal 9.8/10 Exceptional (14 reviews) "Excellent place to stay. Shelly is an excellent host. Nice location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa H. CA $399 CA $592 total includes taxes & fees Mar 12 - Mar 13 [](https://www.expedia.ca/Front-Royal-Hotels-Stunning-Riverfront-Shenandoah-River-Sleeps-4.h78093042.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=2026-03-19&endDate=2026-03-20®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.ca/deals?rfrr=AA_SPRING_PROMO_553248635975865285) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.ca/Hotel-Search?destination=Chester+Gap%2C+Virginia%2C+United+States+of+America®ionId=553248635975865285&latLong=38.853485%2C-78.134962&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=CABIN) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Chester+Gap%2C+Virginia%2C+United+States+of+America®ionId=553248635975865285&latLong=38.853485%2C-78.134962&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=VACATION_HOME) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Chester+Gap%2C+Virginia%2C+United+States+of+America®ionId=553248635975865285&latLong=38.853485%2C-78.134962&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=COTTAGE) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Chester+Gap%2C+Virginia%2C+United+States+of+America®ionId=553248635975865285&latLong=38.853485%2C-78.134962&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=APARTMENT) Villas [](https://www.expedia.ca/Hotel-Search?destination=Chester+Gap%2C+Virginia%2C+United+States+of+America®ionId=553248635975865285&latLong=38.853485%2C-78.134962&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=VILLA) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Chester+Gap%2C+Virginia%2C+United+States+of+America®ionId=553248635975865285&latLong=38.853485%2C-78.134962&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&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.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 ![Ramada by Wyndham Strasburg/Shenandoah Valley](https://images.trvl-media.com/lodging/2000000/1250000/1246400/1246311/220661a2_y.jpg) ### Ramada by Wyndham Strasburg/Shenandoah Valley 6/10 Okay "Bed was clean and comfortable. Enjoyed the online check-in/ check-out procedure. Restaurant onsite was very good. I recommend it! The building had a stale smell to it, including our room. The furniture was old and in poor condition. Many restrooms were out of order and only one slow elevator worked. It kind of needs a complete overhaul. " [](https://expedia.ca/Winchester-Hotels-Ramada-By-Wyndham-Strasburg.h1246311.Hotel-Information) ![Star view cabin-Riverfront ](https://images.trvl-media.com/lodging/31000000/30790000/30788500/30788475/4b1ea453_y.jpg) ### Star view cabin-Riverfront 10/10 Excellent "The cabin is great, perfect for my wife and me. The bed was comfy and the gas fireplace was a plus. We also enjoyed the ease of access to the hot tub and the beautiful views. We loved being able to have our small dog with us, and she gave the experience two paws up! One thing would've been helpful, and that's a larger skillet. There was just one, and it was a bit small, even for the two of us. " [](https://expedia.ca/Rileyville-Hotels-Star-View-Cabin-Riverfront.h30788475.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) ### Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo 10/10 Excellent "Beautiful view could not be beat and the cabin was cozy. Enjoyed playing some of the board games there and the fireplace. Host was quick to respond whenever we messaged. " [](https://expedia.ca/Winchester-Hotels-Log-Cabin-With-A-Spectacular-View-Of-The-Shenandoah-River-And-The-Massanutten-Mo.h26968349.Hotel-Information) ![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 "The check-in staff was excellent. We feel like she went out of her way to take care of us. Also, the restaurant served an excellent dinner. We highly recommend this hotel." [](https://expedia.ca/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.Hotel-Information) ![Fairfield Inn & Suites Strasburg Shenandoah Valley](https://images.trvl-media.com/lodging/3000000/2240000/2230900/2230885/ce971938_y.jpg) ### Fairfield Inn & Suites Strasburg Shenandoah Valley 6/10 Okay "We were told there wasn’t many people staying on property but we received a room with dirty sheets, stuff on the wall, and the mirror cracked. " [](https://expedia.ca/Winchester-Hotels-Fairfield-Inn-Suites-Strasburg-Shenandoah-Valley.h2230885.Hotel-Information) ![Secluded River Cabin Getaway (Masten Cabin)](https://images.trvl-media.com/lodging/58000000/57920000/57914400/57914375/915d9007_y.jpg) ### Secluded River Cabin Getaway (Masten Cabin) 10/10 Excellent "Had everything we needed to feel at home great location we will be booking again " [](https://expedia.ca/Strasburg-Hotels-Secluded-River-Cabin-Getaway.h57914375.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 "Room was great. Front desk man was very friendly and gracious. Breakfast was fine, staff friendly, and a great job of keeping everything spotless. Bob Stanley" [](https://expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information) ![Country Inn & Suites by Radisson, Winchester, VA](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/a391dd61_y.jpg) ### Country Inn & Suites by Radisson, Winchester, VA 10/10 Excellent "Convenient location, clean room, and nice breakfast " [](https://expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) ![Hampton Inn Front Royal](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/810f7f7f_y.jpg) ### Hampton Inn Front Royal 10/10 Excellent "Great one night stay! Friendly, welcoming staff! Room was clean and comfortable. Location was perfect- near dining and highway! " [](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.Hotel-Information) ## Find out more about Chester Gap ## Chester Gap Cottages information | Number of reviews | 52 | | ----------------- | ----------- | | Accommodation | 54 Cottages | | Lowest Price | CA $305 | | Highest Price | CA $598 | ## 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) - [Hotels near Blue Ridge Shadows Golf Club ](https://www.expedia.ca/Blue-Ridge-Shadows-Golf-Club-Hotels.0-l553248621532661832-0.Travel-Guide-Filter-Hotels) - [Rappahannock County Hotels ](https://www.expedia.ca/Destinations-In-Rappahannock-County.d3000400038.Hotel-Destinations) - 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