Title: Upperville Villas from CA $493 | 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) ![Hiking Sky Meadows State Park...](https://images.trvl-media.com/place/553248621532661864/008a9705-5d69-4bff-87e9-dd23f82e56ed.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Michael Gibson # Search Upperville Villa Rentals from CA $493 - ![](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 [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Upperville villas ![Exterior](https://images.trvl-media.com/lodging/118000000/117640000/117633900/117633812/53039378.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117640000/117633900/117633812/da130fd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels, soap, shampoo](https://images.trvl-media.com/lodging/118000000/117640000/117633900/117633812/a06f42c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/118000000/117640000/117633900/117633812/0a67bc1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Red Cherry Oasis - Charming 2 bedroom villa with AC, WiFi in serene Aldie [](https://www.expedia.ca/Aldie-Hotels-Red-Cherry-Oasis-Charming-2-Bedroom-Villa-With-AC.h117633812.Hotel-Information) Aldie 9.0/10 Wonderful (4) "Our experience at Red Cherry Oasis was wonderful. The villa was clean and the host was responsive. The community is very family-friendly and close to shopping and local attractions. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tracy G. CA $220 CA $493 total includes taxes & fees Jan 3 - Jan 4, 2026 [](https://www.expedia.ca/Aldie-Hotels-Red-Cherry-Oasis-Charming-2-Bedroom-Villa-With-AC.h117633812.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=2026-01-12&endDate=2026-01-13®ionId=184116&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%2FUpperville-Villas.d184116-aaVillas.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FUpperville-Villas.d184116-aaVillas.Travel-Guide-Accommodation) ## Top Upperville Hotel Reviews ![La Quinta Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb_y.jpg) ### La Quinta Inn & Suites by Wyndham Winchester 10/10 Excellent "Everything was great" [](https://expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Hotel Burg](https://images.trvl-media.com/lodging/115000000/114280000/114275900/114275854/2337af83_y.jpg) ### Hotel Burg 10/10 Excellent "Very clean, new, quiet. Friendly staff. Loved it." [](https://expedia.ca/Leesburg-Hotels-Hotel-Burg.h114275854.Hotel-Information) ![TRU By Hilton Winchester](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/b9c1387b_y.jpg) ### TRU By Hilton Winchester 10/10 Excellent "Clean rooms, courteous staff" [](https://expedia.ca/Winchester-Hotels-TRU-By-Hilton-Winchester.h39493421.Hotel-Information) ![Travelodge by Wyndham Winchester](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/9d44a9b1_y.jpg) ### Travelodge by Wyndham Winchester 10/10 Excellent "All of the above mentioned and a great, nutritious and varied breakfast. Also, both regular and decaf coffee were available in the breakfast area whenever I wanted it. Lastly, plentiful parking." [](https://expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ![Microtel Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657_y.jpg) ### Microtel Inn & Suites by Wyndham Winchester 10/10 Excellent "My go to when visiting my parents. No frills, great price. Clean, decent coffee and breakfast (what you expect for the price) nice gym. Rooms are quiet. Bed comfortable and super easy parking. " [](https://expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.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 "Very nice hotel for an overnight stop on way north. Right next to I-81 so we asked for (and received) a room on the parking lot side. Clean and comfortable room, but be sure to unfold the pillows before trying to sleep! Definitely recommend the nearby Bruster's Real Ice Cream for a treat, and the Sclafani's New York Bagels and Bread for breakfast!" [](https://expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information) ![The George Washington Hotel, A Wyndham Grand Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5a07226c_y.jpg) ### The George Washington Hotel, A Wyndham Grand Hotel 10/10 Excellent "It would be nice if they had a business center that was actually a business center and not a storage room" [](https://expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![Clarion Inn Harpers Ferry - Charles Town](https://images.trvl-media.com/lodging/1000000/980000/977400/977326/a9078e90_y.jpg) ### Clarion Inn Harpers Ferry - Charles Town 10/10 Excellent "Rooms were clean, staffs were friendly and the breakfast was good." [](https://expedia.ca/Martinsburg-Hotels-Clarion-Inn-Harpers-Ferry-Charles-Town.h977326.Hotel-Information) ![Quality Inn Winchester](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/0fd2f943_y.jpg) ### Quality Inn Winchester 10/10 Excellent "Great staff, clean room" [](https://expedia.ca/Winchester-Hotels-Quality-Inn.h172810.Hotel-Information) ## Find out more about Upperville ## Upperville Villas information | Number of reviews | 3 | | ----------------- | -------- | | Accommodation | 6 Villas | | Lowest Price | CA $493 | | Highest Price | CA $493 | ## Frequently asked questions ### Why book your villa in Upperville with Expedia? ### How can I find cheap villas in Upperville? ## 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) - 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