Title: Chester Gap B&B: Find the Best Bed and Breakfast from CA $475 | 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 Next weekend [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=553248635975865285&startDate=2026-02-27&endDate=2026-03-01&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=553248635975865285&startDate=2026-03-06&endDate=2026-03-08&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=553248635975865285&startDate=2026-03-20&endDate=2026-03-22&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=553248635975865285&startDate=2026-04-17&endDate=2026-04-19&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester Gap bed & breakfast ![Exterior](https://images.trvl-media.com/lodging/20000000/19130000/19126100/19126061/6e95af26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/20000000/19130000/19126100/19126061/e1bc7cf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/20000000/19130000/19126100/19126061/df92df6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Private Bathroom (Windsor Suite) | Deep soaking bathtub](https://images.trvl-media.com/lodging/20000000/19130000/19126100/19126061/c20a2340.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Glen Gordon Manor [](https://www.expedia.ca/Huntly-Hotels-Glen-Gordon-Manor.h19126061.Hotel-Information) Huntly 9.8/10 Exceptional (96 reviews) "Staff was all very attentive. Nice and peaceful stay. Wife loved it, very vintage and clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) KYLE CA $435 CA $475 total includes taxes & fees Mar 16 - Mar 17 [](https://www.expedia.ca/Huntly-Hotels-Glen-Gordon-Manor.h19126061.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/28000000/27140000/27137100/27137088/a8e8b9f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 Queen Bed, Balcony](https://images.trvl-media.com/lodging/28000000/27140000/27137100/27137088/e8898863.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/28000000/27140000/27137100/27137088/e996c5c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/28000000/27140000/27137100/27137088/3b25e32e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hopkins Ordinary Bed Breakfast and Ale Works [](https://www.expedia.ca/Sperryville-Hotels-Hopkins-Ordinary-Bed-Breakfast-And-Ale-Works.h27137088.Hotel-Information) Sperryville 9.8/10 Exceptional (32 reviews) "Great place. Good food, great beer." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Phil [](https://www.expedia.ca/Sperryville-Hotels-Hopkins-Ordinary-Bed-Breakfast-And-Ale-Works.h27137088.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/27000000/26680000/26679800/26679788/8458539f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/27000000/26680000/26679800/26679788/1a36bdf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, 1 King Bed](https://images.trvl-media.com/lodging/27000000/26680000/26679800/26679788/390101c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/27000000/26680000/26679800/26679788/fdad32ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gay Street Inn [](https://www.expedia.ca/Washington-Hotels-Gay-Street-Inn.h26679788.Hotel-Information) Washington 10/10 Exceptional (34 reviews) "Beautiful historic Inn with incredible owners and service. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Renee CA $490 CA $528 total includes taxes & fees Mar 11 - Mar 12 [](https://www.expedia.ca/Washington-Hotels-Gay-Street-Inn.h26679788.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=2026-03-04&endDate=2026-03-05®ionId=553248635975865285&adults=2&lodging=BED_AND_BREAKFAST&sort=RECOMMENDED&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) ![](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-Bed-And-Breakfast.d553248635975865285-aaBedAndBreakfast.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Gap-Bed-And-Breakfast.d553248635975865285-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Chester Gap Hotel Reviews ![Comfort Inn & Suites Winchester](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/cf4c2663_y.jpg) ### Comfort Inn & Suites Winchester 10/10 Excellent "clean, well appointed, very nice staff" [](https://expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.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.ca/Winchester-Hotels-Ramada-By-Wyndham-Strasburg.h1246311.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 "Room was very clean, hotel was very clean and quiet. Nice place to stay " [](https://expedia.ca/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.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.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.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.ca/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.ca/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.ca/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.ca/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.ca/Winchester-Hotels-Baymont-By-Wyndham-Front-Royal-Near-Shenandoah-National-Park.h10535.Hotel-Information) ## Find out more about Chester Gap ## Chester Gap B&B information | Number of reviews | 96 | | ----------------- | ------- | | Accommodation | 3 B&B | | Lowest Price | CA $475 | | Highest Price | CA $528 | ## Frequently asked questions ### Searching for B&Bs in Chester Gap? ### Are you thinking about B&Bs over traditional hotel rooms? ### What are the best bed and breakfasts in Chester Gap? ### When should I book my B&B in Chester Gap? ### What is there to do in Chester Gap? ## Explore a world of travel with Expedia - Lodging - 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