Title: Chester Gap Guest Houses from CA $548 | 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 Guest Houses in Chester Gap from CA $548 ![](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 [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635975865285&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635975865285&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=553248635975865285&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635975865285&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chester Gap Guest Houses ![Interior](https://images.trvl-media.com/lodging/110000000/109390000/109384200/109384177/w1348h899x0y1-14db6c75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/110000000/109390000/109384200/109384177/w1349h899x1y1-276582f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/110000000/109390000/109384200/109384177/1efb01b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109390000/109384200/109384177/9950b501.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Guest House at Mt Independence Delaplane 10/10 Exceptional (4) "Great property, conveniently located to attractions. Host was extremely responsive and friendly. Home and surrounding property was immaculate. We will be staying here again when back in the area. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Scott S. CA $238 CA $548 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Delaplane-Hotels-Guest-House-At-Mt-Independence.h109384177.Hotel-Information) ![Premier Villa, 1 King Bed, Mountain View | Terrace/patio](https://images.trvl-media.com/lodging/14000000/13400000/13391000/13390991/a36aa267.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Romantic Room, 1 King Bed, Non Smoking (The Cottage)](https://images.trvl-media.com/lodging/14000000/13400000/13391000/13390991/4c371a72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/14000000/13400000/13391000/13390991/12f25c36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/14000000/13400000/13391000/13390991/445f5296.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### White Moose Inn Washington 9.8/10 Exceptional (146) "Amazing trip! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rebecca CA $548 CA $591 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Washington-Hotels-White-Moose-Inn.h13390991.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/39540000/39532100/39532065/baa1c471.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/40000000/39540000/39532100/39532065/3166dbe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/40000000/39540000/39532100/39532065/a816723a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/40000000/39540000/39532100/39532065/99c8f223.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment The Plains 10/10 Exceptional (6) "Absolutely loved our stay at Unicorn Hollow. So peaceful. Clean and had everything you needed. Loved the horses and Guiseppe (the donkey) along with the deer and alpacas. Can stroll about the property. Anna and Pino were wonderful to meet. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jan I. CA $346 CA $564 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Marshall-Hotels-Private-Unicorn-Hollow-AptWineries-Twilight-PoloMiddleburg.h39532065.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=2025-11-08&endDate=2025-11-09®ionId=553248635975865285&adults=2&lodging=GUEST_HOUSE&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-Guest-Houses.d553248635975865285-aaGuestHouses.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Gap-Guest-Houses.d553248635975865285-aaGuestHouses.Travel-Guide-Accommodation) ## Top Chester Gap Hotel Reviews ![Hampton Inn Front Royal](//images.trvl-media.com/lodging/1000000/900000/892600/892585/737257e0_y.jpg) ### Hampton Inn Front Royal 10/10 Excellent "We thoroughly enjoyed all aspects of our stay, and look forward to the next time." [](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.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 "Our room was great and fresh. Dinner at the hotel restaurant was delicious and the staff was friendly and welcoming. " [](https://expedia.ca/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.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 rooms and comfortable beds and bedding. Plentiful bath towels. Convenient location " [](https://expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.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 "It was good." [](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 "Everythign was great. staff was friendly and room was clean. Complimentary breakfast was good. " [](https://expedia.ca/Winchester-Hotels-TownePlace-Suites-By-Marriott-Front-Royal.h36342604.Hotel-Information) ![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 "Always a pleasure staying here " [](https://expedia.ca/Winchester-Hotels-Fairfield-Inn-Suites-Strasburg-Shenandoah-Valley.h2230885.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 "Staff was friendly. Room was clean. Restaurant attached to hotel was tasty. Thumbs up." [](https://expedia.ca/Winchester-Hotels-Ramada-By-Wyndham-Strasburg.h1246311.Hotel-Information) ![Baymont by Wyndham Front Royal Near Shenandoah National Park](//images.trvl-media.com/lodging/1000000/20000/10600/10535/071235b5_y.jpg) ### Baymont by Wyndham Front Royal Near Shenandoah National Park 10/10 Excellent "The staff was very friendly and helpful. The hotel is older but clean, quit and comfortable. The breakfast had a great variery and was well stocked. There was plenty of seating. We stayed for one night on our way to Shenandoah and Luray Caverns." [](https://expedia.ca/Winchester-Hotels-Baymont-By-Wyndham-Front-Royal-Near-Shenandoah-National-Park.h10535.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 "Stay here every year in October on a fall foliage trip to Shenandoah. Never disappoints. Will book again next year!" [](https://expedia.ca/Winchester-Hotels-Super-8-By-Wyndham-Front-Royal.h855557.Hotel-Information) ## Find out more about Chester Gap ## Chester Gap Guest Houses information | Number of reviews | 155 | | --- | --- | | Accommodation | 5 Guest Houses | | Lowest Price | CA $548 | | Highest Price | CA $591 | ## 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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