Title: Upperville Guest Houses from CA $525 | Expedia.ca [Hotels in Upperville](https://expedia.ca/Upperville-Hotels.d184116.Travel-Guide-Hotels)[Vacation Rentals in Upperville](https://expedia.ca/Upperville-Vacation-Rentals.d184116.Travel-Guide-VacationRentals)[Upperville Car Rentals](https://expedia.ca/Car-Rentals-In-Upperville.d184116.Car-Rental-Guide)[Upperville Vacation Packages](https://expedia.ca/Upperville.d184116.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Guest Houses in Upperville from CA $525 - ![](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 [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2025-12-12&endDate=2025-12-14&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2026-01-09&endDate=2026-01-11&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Upperville 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) ![Terrace/patio](https://images.trvl-media.com/lodging/110000000/109390000/109384200/109384177/1efb01b0.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) ![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) "The house was perfect for our family gathering. We ate most of our meals out but the kitchen was well equipped. Stephen was very easy to work with and helped us out when our plans had to be adjusted. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) deb l. CA $210 CA $515 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Delaplane-Hotels-Guest-House-At-Mt-Independence.h109384177.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/91000000/90760000/90758600/90758569/3fdfbac9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/91000000/90760000/90758600/90758569/51d4e57d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/91000000/90760000/90758600/90758569/2aa76f56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/91000000/90760000/90758600/90758569/dad200f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Briar Patch Bed & Breakfast Inn Middleburg 7.6/10 Good (10) "Property seems to have deteriorated over the years. Needs cleaning up. Hot tub water was green." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Samantha [](https://www.expedia.ca/Middleburg-Hotels-Briar-Patch-Bed-Breakfast-Inn.h90758569.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) ![Property grounds](https://images.trvl-media.com/lodging/40000000/39540000/39532100/39532065/99c8f223.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) ![Terrace/patio](https://images.trvl-media.com/lodging/40000000/39540000/39532100/39532065/3166dbe9.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) "This is one of the best VRBO places we have stayed. It is very well stocked with everything you would need. The bright interior is lovely. You feel like you are staying in someone’s home. The grounds are beautiful and it is very private and peaceful. Pino is a marvelous host. Just be aware that the house is at the end of a long country lane. I would assuredly stay again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carolyn C. CA $347 CA $565 total includes taxes & fees Nov 17 - Nov 18 [](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=2025-11-29&endDate=2025-11-30®ionId=184116&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%2FUpperville-Guest-Houses.d184116-aaGuestHouses.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FUpperville-Guest-Houses.d184116-aaGuestHouses.Travel-Guide-Accommodation) ## Top Upperville Hotel Reviews ### Travelodge by Wyndham Winchester 10/10 Excellent "The room was cleaned and fully stocked with supplies daily. A descent breakfast. Convenient location." [](https://expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ### Hampton Inn & Suites Charles Town 10/10 Excellent "Room was beautiful" [](https://expedia.ca/Martinsburg-Hotels-Hampton-Inn-Suites-Charles-Town.h4532660.Hotel-Information) ![Red Roof Inn Leesburg, VA](//images.trvl-media.com/lodging/1000000/20000/17600/17577/610f0a4e_y.jpg) ### Red Roof Inn Leesburg, VA 10/10 Excellent "Clean nice rooms , friendly staff and helpful , convenient " [](https://expedia.ca/Leesburg-Hotels-Red-Roof-Inn-Leesburg.h17577.Hotel-Information) ### Holiday Inn Express Charles Town by IHG 10/10 Excellent "This was a wonderful property and I would absolutely stay here again. It is close to stores, restaurants, gas, and the casino. Staff were very friendly, and the breakfast was delicious! Spacious, clean, and quiet rooms! I truly enjoyed my stay here!" [](https://expedia.ca/Martinsburg-Hotels-Holiday-Inn-Express-Charles-Town.h1554858.Hotel-Information) ### Country Inn & Suites by Radisson, Winchester, VA 10/10 Excellent "Ws a clean and comfy place" [](https://expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) ### Microtel Inn & Suites by Wyndham Winchester 10/10 Excellent "Quick, efficient and friendly. Just like I like it " [](https://expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information) ### Hilton Garden Inn Dulles North 10/10 Excellent "Clean room and the staff was excellent. " [](https://expedia.ca/Ashburn-Hotels-Hilton-Garden-Inn-Dulles-North.h2335184.Hotel-Information) ### Clarion Hotel & Conference Center Leesburg 8/10 Good "Solid but dated property" [](https://expedia.ca/Leesburg-Hotels-Clarion-Hotel-Conference-Center-Leesburg.h24372.Hotel-Information) ### The George Washington Hotel, A Wyndham Grand Hotel 10/10 Excellent "Yes great hotel!!" [](https://expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ## Find out more about Upperville ## Upperville Guest Houses information | Number of reviews | 19 | | --- | --- | | Accommodation | 10 Guest Houses | | Lowest Price | CA $525 | | Highest Price | CA $565 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [Ashville Hotels](https://www.expedia.ca/Ashville-Hotels.d553248635975846883.Travel-Guide-Hotels) - [Luxury Hotels in Blue Ridge](https://www.expedia.ca/Blue-Ridge-Hotels-Luxury-Hotel.0-0-d553248635976006713-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Marriott Hotels & Resorts in Blue Ridge](https://www.expedia.ca/Blue-Ridge-Hotels-Marriott-Hotels-Resorts.0-0-d553248635976006713--bMarriottHotelsResorts.Travel-Guide-Filter-Hotels) - [Blue Ridge Hotels](https://www.expedia.ca/Blue-Ridge-Hotels.d553248635976006713.Travel-Guide-Hotels) - [Aparthotels in Bluemont](https://www.expedia.ca/Bluemont-Apart-Hotels.d6348602-aaApartHotels.Travel-Guide-Accommodation) - 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