Title: Book The Best Hotels in Upperville, VA for 2025 from CA $99 - Fully Refundable Options - Expedia.ca [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 # Find hotels in Upperville, VA from CA $99 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Go beyond your typical stay in Upperville Spa [](https://www.expedia.ca/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America®ionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2025-10-14&d1=2025-10-14&endDate=2025-10-16&d2=2025-10-16&amenities=SPA_ON_SITE) Cabin [](https://www.expedia.ca/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America®ionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2025-10-14&d1=2025-10-14&endDate=2025-10-16&d2=2025-10-16&lodging=CABIN) Family friendly [](https://www.expedia.ca/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America®ionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2025-10-14&d1=2025-10-14&endDate=2025-10-16&d2=2025-10-16&travelerType=family_friendly) Cottage [](https://www.expedia.ca/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America®ionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2025-10-14&d1=2025-10-14&endDate=2025-10-16&d2=2025-10-16&lodging=COTTAGE) Apart­ment [](https://www.expedia.ca/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America®ionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2025-10-14&d1=2025-10-14&endDate=2025-10-16&d2=2025-10-16&lodging=APARTMENT) Hot tub [](https://www.expedia.ca/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America®ionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2025-10-14&d1=2025-10-14&endDate=2025-10-16&d2=2025-10-16&amenities=HOT_TUB) Pool [](https://www.expedia.ca/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America®ionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2025-10-14&d1=2025-10-14&endDate=2025-10-16&d2=2025-10-16&amenities=POOL) Pet friendly [](https://www.expedia.ca/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America®ionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2025-10-14&d1=2025-10-14&endDate=2025-10-16&d2=2025-10-16&amenities=PETS) Chalet [](https://www.expedia.ca/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America®ionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2025-10-14&d1=2025-10-14&endDate=2025-10-16&d2=2025-10-16&lodging=CHALET) Farm [](https://www.expedia.ca/Hotel-Search?destination=Upperville%2C+Virginia%2C+United+States+of+America®ionId=184116&latLong=38.992939%2C-77.886375&adults=2&startDate=2025-10-14&d1=2025-10-14&endDate=2025-10-16&d2=2025-10-16&lodging=AGRITOURISM) ## Check prices for these dates Tonight [Sep 30 - Oct 1](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2025-09-30&endDate=2025-10-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 1 - Oct 2](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2025-10-01&endDate=2025-10-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Compare 704 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable. ![Indoor pool](https://images.trvl-media.com/lodging/1000000/980000/977400/977326/a9078e90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/980000/977400/977326/75fa7cd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/980000/977400/977326/cba53522.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/980000/977400/977326/627db10f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Clarion Inn Harpers Ferry - Charles Town Harpers Ferry 8.0/10 Very good (1035) "Great stay" CA $139 CA $156 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Martinsburg-Hotels-Clarion-Inn-Harpers-Ferry-Charles-Town.h977326.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/7000000/6030000/6022300/6022232/21ca3455.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; local cuisine](https://images.trvl-media.com/lodging/7000000/6030000/6022300/6022232/b8f43b35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/7000000/6030000/6022300/6022232/8a0b17e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Couples treatment rooms, sauna, hot tub, steam room, hot springs](https://images.trvl-media.com/lodging/7000000/6030000/6022300/6022232/43873b99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Salamander Resort And Spa Middleburg 9.2/10 Wonderful (365) "The property is at a close proximity to the downtown area. We were able to walk everywhere. Our room was spacious and immaculate. " CA $730 CA $905 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Middleburg-Hotels-Salamander-Resort-And-Spa.h6022232.Hotel-Information) ![2 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5a07226c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/d6b37fa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/a8e7d0d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5707228d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The George Washington Hotel, A Wyndham Grand Hotel Old Town Winchester 9.4/10 Exceptional (1004) "Perfect location to visit for business or pleasure!" CA $176 CA $200 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![Rooftop terrace](https://images.trvl-media.com/lodging/2000000/1560000/1554900/1554858/89e72fbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1560000/1554900/1554858/202ce6ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed with Sofa bed](https://images.trvl-media.com/lodging/2000000/1560000/1554900/1554858/8910bd36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free buffet breakfast](https://images.trvl-media.com/lodging/2000000/1560000/1554900/1554858/fcd6e875.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Charles Town by IHG Charles Town 9.2/10 Wonderful (1000) "Had a great stay, close to area attractions" CA $160 CA $181 total includes taxes & fees Oct 2 - Oct 3 [](https://www.expedia.ca/Martinsburg-Hotels-Holiday-Inn-Express-Charles-Town.h1554858.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/74000000/73570000/73560200/73560131/79fcba7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/74000000/73570000/73560200/73560131/0d6997c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed, City View | City view](https://images.trvl-media.com/lodging/74000000/73570000/73560200/73560131/20a3d6ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, dinner, brunch served; American cuisine ](https://images.trvl-media.com/lodging/74000000/73570000/73560200/73560131/07cd4f83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Haymarket Haymarket 9.4/10 Exceptional (225) "Great place to stay" CA $216 CA $250 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Haymarket-Hotels-Hilton-Garden-Inn-Haymarket.h73560131.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/77000000/76880000/76876900/76876848/fd85fd97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/77000000/76880000/76876900/76876848/a19abecc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/77000000/76880000/76876900/76876848/29d89638.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/77000000/76880000/76876900/76876848/a984ecc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Charles Town - Hollywood Casino Charles Town 8.6/10 Excellent (494) "It is convenient to the casino and racetrack. The continental breakfast was average at best. For a tremendous breakfast try the Charlestown Family Diner across the street from this property." CA $145 CA $176 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Charles-Town-Hotels-The-Inn-At-Charles-Town.h76876848.Hotel-Information) ![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/3000000/2940000/2933800/2933741/6a58d545.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Studio, Non Smoking, Refrigerator & Microwave](https://images.trvl-media.com/lodging/3000000/2940000/2933800/2933741/671381db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Studio, Non Smoking, Refrigerator & Microwave](https://images.trvl-media.com/lodging/3000000/2940000/2933800/2933741/c1ac9b70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2940000/2933800/2933741/5aa6585c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Extended Stay America Select Suites Gainesville Gainesville 6.2/10 (462) "Great stay. " CA $117 CA $133 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Gainesville-Hotels-WoodSpring-Suites-Gainesville-VA.h2933741.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/b1a55fc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/41cd029b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/ffce1877.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Winchester Winchester 9.2/10 Wonderful (2175) "Nicely renovated hotel with great room. " CA $151 CA $164 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652870/0a2d8398.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652870/61e9f06d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast meal](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652870/a5945e18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652870/3c75b4dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Candlewood Suites Winchester by IHG Winchester 8.8/10 Excellent (515) "The suites we're clean and spacious. The perfect stay for a family weekend!" CA $129 CA $141 total includes taxes & fees Oct 2 - Oct 3 [](https://www.expedia.ca/Winchester-Hotels-Candlewood-Suites-Winchester.h1652870.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1830000/1828900/1828858/50197254.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1830000/1828900/1828858/2387a9d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/2000000/1830000/1828900/1828858/95b54325.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1830000/1828900/1828858/028e64b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn by Hilton Gainesville-Haymarket Gainesville 8.8/10 Excellent (956) "Nice hotel, convenient location, lots of shopping and dining options close by." CA $176 CA $201 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Gainesville-Hotels-Hampton-Inn-By-Hilton-Gainesville-Haymarket.h1828858.Hotel-Information) ![Premium bedding, pillowtop beds, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/73000000/72030000/72023600/72023562/fc21f98c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/73000000/72030000/72023600/72023562/w3000h1998x0y0-156eb7d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Laundry room](https://images.trvl-media.com/lodging/73000000/72030000/72023600/72023562/617e781a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free continental breakfast](https://images.trvl-media.com/lodging/73000000/72030000/72023600/72023562/c6b45b54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Travelodge By Wyndham Charles Town/Harpers Ferry Charles Town 7.0/10 Good (243) "Wasn’t the cleanest but it’s good for a quick stop" CA $88 CA $99 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Charles-Town-Hotels-Travelodge-By-Wyndham-Charles-TownHarpers-Ferry.h72023562.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/1000000/20000/10100/10086/ad87d83f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/1000000/20000/10100/10086/5d8b5ff4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/10100/10086/80605b25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/20000/10100/10086/af8ba0cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Baymont by Wyndham Warrenton Warrenton 6.4/10 (1000) "Staff had easy check in and out " CA $103 CA $111 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Warrenton-Hotels-Baymont-By-Wyndham-Warrenton.h10086.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/0fd2f943.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/7e51069b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/cd85ec17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/c7da6581.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Winchester Winchester 9.2/10 Wonderful (1000) "We will be staying there again" CA $117 CA $127 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Winchester-Hotels-Quality-Inn.h172810.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/33000000/32440000/32431200/32431174/6cb6a218.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/33000000/32440000/32431200/32431174/56e9357e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Middleburg Cottage | Living area](https://images.trvl-media.com/lodging/33000000/32440000/32431200/32431174/f6f51ac5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/33000000/32440000/32431200/32431174/c883192a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Red Fox Inn & Tavern Middleburg 9.6/10 Exceptional (391) "Beautiful old inn with lots of character. Very friendly staff, spacious room, incredibly comfortable bed!" CA $472 CA $538 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Middleburg-Hotels-The-Red-Fox-Inn-Tavern.h32431174.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/c68804b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed (Additional Living Area)](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/aeec97ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/b6f40366.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/ee4df7fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Winchester Se-Historic Gateway by IHG Winchester 9.0/10 Wonderful (1016) "Great hotel! " CA $129 CA $145 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/5000000/4540000/4532700/4532660/4441f7ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4540000/4532700/4532660/ad3e0e1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/5000000/4540000/4532700/4532660/39c165a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/5000000/4540000/4532700/4532660/ec2efbf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Charles Town Charles Town 9.4/10 Exceptional (1004) "Overall it was a nice stop over stay" CA $176 CA $197 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Martinsburg-Hotels-Hampton-Inn-Suites-Charles-Town.h4532660.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/w4000h2662x0y0-b556d792.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/fb0da257.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/b20fa3f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/27064e98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Winchester Winchester 9.0/10 Wonderful (768) "This was a very clean well run hotel and the staff was friendly and accomodating. Would definitely stay here again." CA $135 CA $147 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Winchester-Hotels-Fairfield-Inn-Suites-By-Marriott-Winchester.h1066410.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/1600/1578/81ded6bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Room, 1 King Bed (Smoke Free)](https://images.trvl-media.com/lodging/1000000/10000/1600/1578/8dd8ff22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/10000/1600/1578/4f2ee97c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/10000/1600/1578/74ddf85a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Red Roof Inn Warrenton Warrenton 6.2/10 (770) ""Had a pleasant stay at Red Roof Inn — the room was clean and comfortable, perfect for a quick stop. The price was affordable, and the location was convenient with easy access to nearby restaurants and highways. Great value for the money!" " CA $120 CA $131 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Warrenton-Hotels-Red-Roof-Inn-Warrenton.h1578.Hotel-Information) ![Premium bedding, down comforters, in-room safe, individually decorated](https://images.trvl-media.com/lodging/2000000/1370000/1360400/1360309/e6e66ad4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/2000000/1370000/1360400/1360309/c0f63216.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 9:00 AM to 8:00 PM, sun loungers](https://images.trvl-media.com/lodging/2000000/1370000/1360400/1360309/0a61ab6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch served; local and international cuisine](https://images.trvl-media.com/lodging/2000000/1370000/1360400/1360309/fb2943f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Goodstone Inn & Restaurant Middleburg 9.6/10 Exceptional (47) "It was a delightful quaint exclusive country inn - a real treat to stay. " CA $396 CA $575 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Middleburg-Hotels-Goodstone-Inn-Restaurant.h1360309.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1110000/1101900/1101849/5a11bccc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/2000000/1110000/1101900/1101849/820c5413.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Refrigerator](https://images.trvl-media.com/lodging/2000000/1110000/1101900/1101849/ae854ecc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free on-the-go breakfast](https://images.trvl-media.com/lodging/2000000/1110000/1101900/1101849/60a92697.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Warrenton by IHG Warrenton 8.6/10 Excellent (753) "Staff was very friendly and helpful. Breakfast was good. The room was clean with a nice king size bed." CA $195 CA $213 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Warrenton-Hotels-Holiday-Inn-Express-Hotel-Suites-Warrenton.h1101849.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=2025-10-14&endDate=2025-10-15®ionId=184116&adults=2&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-Hotels.d184116.Travel-Guide-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FUpperville-Hotels.d184116.Travel-Guide-Hotels) ## More cheap stays in Upperville ![Travelodge by Wyndham Winchester](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/28616e5b_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Travelodge by Wyndham Winchester 160 Front Royal Pike, Winchester, VA CA $100 CA $109 total Oct 1 - Oct 2 includes taxes & fees 8.4/10 Very Good! (1,100 reviews) [](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?impolicy=resizecrop&rw=402&ra=fit) ### Microtel Inn & Suites by Wyndham Winchester 150 Faraday Plaza, Winchester, VA CA $108 CA $117 total Oct 31 - Nov 1 includes taxes & fees 9/10 Wonderful! (1,346 reviews) [](https://expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information) ![Baymont by Wyndham Warrenton](https://images.trvl-media.com/lodging/1000000/20000/10100/10086/ad87d83f_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Baymont by Wyndham Warrenton 7379 Comfort Inn Drive, U.S. 29, Warrenton, VA CA $103 CA $111 total Oct 6 - Oct 7 includes taxes & fees 6.4/10 (1,002 reviews) [](https://expedia.ca/Warrenton-Hotels-Baymont-By-Wyndham-Warrenton.h10086.Hotel-Information) ![Hampton Inn Winchester-University/Mall Area](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/17b0fc68_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hampton Inn Winchester-University/Mall Area 640 East Jubal Early Drive, Winchester, VA CA $115 CA $130 total Oct 31 - Nov 1 includes taxes & fees 9/10 Wonderful! (1,014 reviews) [](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.Hotel-Information) ![SpringHill Suites by Marriott Winchester](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/193cda05_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### SpringHill Suites by Marriott Winchester 280 MARKET STREET, Winchester, VA CA $162 CA $176 total Oct 5 - Oct 6 includes taxes & fees 9.4/10 Exceptional! (726 reviews) [](https://expedia.ca/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information) ![Best Western Leesburg Hotel & Conference Center](https://images.trvl-media.com/lodging/1000000/20000/12700/12669/af96bac4_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Best Western Leesburg Hotel & Conference Center 726 E Market St, Leesburg, VA CA $149 CA $171 total Oct 6 - Oct 7 includes taxes & fees 7.8/10 Good! (1,000 reviews) [](https://expedia.ca/Leesburg-Hotels-Best-Western-Leesburg-Hotel-Conference-Center.h12669.Hotel-Information) ## Hotels in Upperville with star-rating ![5 Star Hotels](https://images.trvl-media.com/lodging/7000000/6030000/6022300/6022232/21ca3455_w.jpg) 5 Star Hotels 2 properties [](https://expedia.ca/5Star-Upperville-Hotels.s50-0-d184116.Travel-Guide-Filter-Hotels) ![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/27700/27700/5ae32850_w.jpg) 4 Star Hotels 12 properties [](https://expedia.ca/4Star-Upperville-Hotels.s40-0-d184116.Travel-Guide-Filter-Hotels) ![3 Star Hotels](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb_w.jpg) 3 Star Hotels 92 properties [](https://expedia.ca/3Star-Upperville-Hotels.s30-0-d184116.Travel-Guide-Filter-Hotels) ![2 Star Hotels](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/28616e5b_w.jpg) 2 Star Hotels 99 properties [](https://expedia.ca/2Star-Upperville-Hotels.s20-0-d184116.Travel-Guide-Filter-Hotels) ## Recent reviews of Upperville hotels ![Hilton Garden Inn Dulles North](//images.trvl-media.com/lodging/3000000/2340000/2335200/2335184/b8108f6b_y.jpg) ### Hilton Garden Inn Dulles North 5/5 Excellent "Very clean! Everyone was so kind!" A verified traveller from Bristol stayed at Hilton Garden Inn Dulles North Posted 2 days ago [](https://expedia.ca/Ashburn-Hotels-Hilton-Garden-Inn-Dulles-North.h2335184.Hotel-Information) ![Hampton Inn Winchester-University/Mall Area](//images.trvl-media.com/lodging/1000000/20000/20000/19971/17b0fc68_y.jpg) ### Hampton Inn Winchester-University/Mall Area 5/5 Excellent "We needed a break with a long family care situation. We took a break and stayed in Winchester and relaxed. Hampton Inn was just perfect. Breakfast was great! Thank you! " A verified traveller stayed at Hampton Inn Winchester-University/Mall Area Posted 3 days ago [](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.Hotel-Information) ![Travelodge by Wyndham Winchester](//images.trvl-media.com/lodging/1000000/10000/9600/9600/28616e5b_y.jpg) ### Travelodge by Wyndham Winchester 5/5 Excellent "Restaurants were nearby and there was plenty of room to walk my dog. The staff was efficient and pleasant. The room felt humid to me. Some maintenance leftovers are sitting around in the back of the property. Overall, nice place to stay but needs some TLC." A verified traveller stayed at Travelodge by Wyndham Winchester Posted 3 days ago [](https://expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ![Holiday Inn Express Charles Town by IHG](//images.trvl-media.com/lodging/2000000/1560000/1554900/1554858/89e72fbd_y.jpg) ### Holiday Inn Express Charles Town by IHG 5/5 Excellent "The hotel is very clean and comfortable. The breakfast is good and the shuttle service is very convenient and was a nice surprise (they'll take you anywhere within 2 miles and pick you up). The staff was all very nice and helpful. " A verified traveller stayed at Holiday Inn Express Charles Town by IHG Posted 5 days ago [](https://expedia.ca/Martinsburg-Hotels-Holiday-Inn-Express-Charles-Town.h1554858.Hotel-Information) ![Courtyard by Marriott Winchester](//images.trvl-media.com/lodging/2000000/1500000/1497900/1497898/8f242b36_y.jpg) ### Courtyard by Marriott Winchester 5/5 Excellent "Very friendly staff and clean facilities." A verified traveller stayed at Courtyard by Marriott Winchester Posted 6 days ago [](https://expedia.ca/Winchester-Hotels-Courtyard-By-Marriott-Winchester.h1497898.Hotel-Information) ![Red Roof Inn Leesburg, VA](//images.trvl-media.com/lodging/1000000/20000/17600/17577/610f0a4e_y.jpg) ### Red Roof Inn Leesburg, VA 5/5 Excellent "staff was exceptional very clean rooms only issue if there was one beds are a little uncomfortable otherwise very nice stay" A verified traveller stayed at Red Roof Inn Leesburg, VA Posted 6 days ago [](https://expedia.ca/Leesburg-Hotels-Red-Roof-Inn-Leesburg.h17577.Hotel-Information) ![Holiday Inn Winchester Se-Historic Gateway by IHG](//images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/c68804b2_y.jpg) ### Holiday Inn Winchester Se-Historic Gateway by IHG 5/5 Excellent "Everything was great except I feel the website should have updated that the restaurant was closed. The beds were amazing and had some issues connecting to the WiFi, but overall a good stay. " A verified traveller stayed at Holiday Inn Winchester Se-Historic Gateway by IHG Posted 6 days ago [](https://expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information) ![The George Washington Hotel, A Wyndham Grand Hotel](//images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5a07226c_y.jpg) ### The George Washington Hotel, A Wyndham Grand Hotel 5/5 Excellent "The beauty of the property to begin with. Old world charm but modernized without detracting from the original character. The grand mailbox, each floor having a mailbox which directly connects with and is fed by gravity to the “grand” collection box on the ground floor! Beautiful! The basement pool is a spectacle to behold! The beauty along with the perfect water temperature provided a perfect ending to our evening!" A verified traveller stayed at The George Washington Hotel, A Wyndham Grand Hotel Posted 7 days ago [](https://expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![Clarion Inn Harpers Ferry - Charles Town](//images.trvl-media.com/lodging/1000000/980000/977400/977326/a9078e90_y.jpg) ### Clarion Inn Harpers Ferry - Charles Town 5/5 Excellent "The close proximity to harpers ferry " A verified traveller stayed at Clarion Inn Harpers Ferry - Charles Town Posted 7 days ago [](https://expedia.ca/Martinsburg-Hotels-Clarion-Inn-Harpers-Ferry-Charles-Town.h977326.Hotel-Information) ## Frequently asked questions ### When is the best time to go to Upperville? > The most popular time to visit Upperville is in May, when the countryside bursts into bloom and the weather is pleasantly warm. With average temperatures hovering around 20°C, it's an excellent period for enjoying the scenic landscapes and participating in outdoor activities such as hiking, horseback riding, and visiting local wineries. > > > > During the peak season, which spans from April to June, Upperville attracts numerous visitors eager to experience its charming atmosphere and vibrant events. This thriving time of year is superb for those who appreciate quality experiences, as you can immerse yourself in the local culture with various festivals and community gatherings. The delightful climate complements outdoor adventures, allowing you to explore the picturesque trails and enjoy the breathtaking views that this region has to offer. > > > > If you're seeking a more tranquil experience, consider visiting in October. This month tends to be less crowded, offering a peaceful ambience while still allowing you to appreciate the stunning fall foliage and partake in seasonal activities like apple picking and vineyard tours. ### Can I cancel my hotel reservation on Expedia? > You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Upperville. ### How can I save on a Upperville hotel booking with Expedia? > With Expedia, you'll unlock our lowest prices by becoming a member. It's free and easy to join, and you can even access member perks too. Just remember to sign in to get our best prices on Upperville hotels. Another way to save is by booking your hotel and flights together on Expedia, where bundling can lead to significant savings. ### How much is the nightly rate at a Upperville hotel? > Prices for hotels in Upperville often vary, but you can find a great deal from CA $99 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. 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