Title: Upperville Apartment Rentals from CA $246 | 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://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Apartment Rentals in Upperville ![](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 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=APARTMENT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=APARTMENT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=APARTMENT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=184116&startDate=2025-12-12&endDate=2025-12-14&adults=2&lodging=APARTMENT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Upperville Apartments ![Property grounds](https://images.trvl-media.com/lodging/84000000/83600000/83591200/83591191/e90c6032.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi](https://images.trvl-media.com/lodging/84000000/83600000/83591200/83591191/4e3d8e20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/84000000/83600000/83591200/83591191/9afb48f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, cookware/dishes/utensils](https://images.trvl-media.com/lodging/84000000/83600000/83591200/83591191/3e63ad06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private apartment on a beautiful private farm! Bluemont 10/10 Exceptional (5) "Stayed here with my 5 month old daughter, my mom and a friend and we had a blast. Kind folks, beautiful grounds and a super cute barn apartment! The fresh flowers in the kitchen were a lovely touch. " CA $189 CA $382 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Bluemont-Hotels-Private-Apartment-On-A-Beautiful-Private-Farm.h83591191.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88520000/88519400/88519350/6413f00b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88520000/88519400/88519350/56b2f1c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/89000000/88520000/88519400/88519350/0beacea7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/89000000/88520000/88519400/88519350/221408fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 1BR Apt Minutes From Skyline Drive!! Amissville 9.6/10 Exceptional (34) "Love the quiet and beautiful surroundings. Very comfortable bed and clean property. Host very responsive. " CA $170 CA $330 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Amissville-Hotels-Cozy-1BR-Apt-Minutes-From-Skyline-Drive.h88519350.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/108000000/107220000/107216300/107216300/w1118h1128x0y0-c29ed3e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107220000/107216300/107216300/w1136h1516x18y15-0867a003.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107220000/107216300/107216300/w1133h1513x0y23-fd248447.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/108000000/107220000/107216300/107216300/a601c23d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rosamond nice downtown studio apt Winchester Historic District 8.0/10 Very good (2) "Small but appropriately priced." CA $154 CA $270 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Winchester-Hotels-Rosamond-Nice-Downtown-Studio-Apt.h107216300.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/119000000/118720000/118716600/118716576/ce69824b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/119000000/118720000/118716600/118716576/e6bb6c5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118720000/118716600/118716576/c0ebbff4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/119000000/118720000/118716600/118716576/9a8809aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries. Bluemont 10/10 Exceptional (1) "Jessica was a wonderful host. Outdoor table was lovely with a great view of a garden with cows as next door neighbors " CA $189 CA $378 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Bluemont-Hotels-Stylish-1-Bd1-Ba-Gardern-Apt-Within-Quaint-Bluemont-Village.h118716576.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/76000000/75840000/75832400/75832325/e75c3693.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/76000000/75840000/75832400/75832325/d9d55f5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/76000000/75840000/75832400/75832325/bc11097d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/76000000/75840000/75832400/75832325/w1284h952x0y7-6504b025.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy English Basement Apt quiet but close to downtown Winchester 9.6/10 Exceptional (7) "Downtown Winchester is charming, and the property was an easy walk from downtown (though in a safe suburban neighborhood). The property itself was just as advertised. I was able to cook meals there; the bed was comfortable; it was much nicer and more varied than a hotel room." CA $140 CA $246 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Winchester-Hotels-Cozy-English-Basement-Apt-Quiet-But-Close-To-Downtown.h75832325.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/76000000/75860000/75853400/75853307/4d85dcf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/76000000/75860000/75853400/75853307/0531b121.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/76000000/75860000/75853400/75853307/6944d33b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/76000000/75860000/75853400/75853307/ccd1e83b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pretty Little Apt by the Train II Old Town Winchester 10/10 Exceptional (4) "Great time. Love this city" CA $182 CA $305 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Winchester-Hotels-Pretty-Little-Apt-By-The-Train-II.h75853307.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/105000000/104060000/104052900/104052857/10901b08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/105000000/104060000/104052900/104052857/48aeb310.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/105000000/104060000/104052900/104052857/4f7ea815.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/105000000/104060000/104052900/104052857/1592611e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apple Mountain Retreat Linden 10/10 Exceptional (19) "Very nice place to stay within convenient distance to Front Royal and Shenandoah Natl Park. " CA $189 CA $324 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Linden-Hotels-Cozy-Spacious-Full-Basement-In-Single-Family-Home-On-Apple-Mountain.h104052857.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/89000000/88210000/88205300/88205213/a2cdbfd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/89000000/88210000/88205300/88205213/ff062017.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/89000000/88210000/88205300/88205213/8bb88bf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, electric kettle, toaster](https://images.trvl-media.com/lodging/89000000/88210000/88205300/88205213/c12bdaf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic apartment in Old Town Warrenton, Virginia Warrenton 9.8/10 Exceptional (54) "Love the 5 minute walk to restaurants! Also loved staying in an apartment in a historic house. Very nicely furnished and had everything we needed. " CA $213 CA $329 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Warrenton-Hotels-Historic-Apartment-In-Old-Town-Warrenton.h88205213.Hotel-Information) ![TV, fireplace, offices](https://images.trvl-media.com/lodging/88000000/87570000/87568700/87568647/73aafe78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/88000000/87570000/87568700/87568647/f1a2a944.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/88000000/87570000/87568700/87568647/af513e86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/88000000/87570000/87568700/87568647/358c6628.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Skyland Hideaway | Mountain Cabin w/ Hot Tub Linden 10/10 Exceptional (14) "We just stayed at SkyLand The house was clean, comfortable and welcoming. Matt is a great host Very responsive. The hot tub needed more water...no big deal. The beds were comfy and the coffee much appreciated upon arrival. Definitely wanna stay again." CA $207 CA $542 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Linden-Hotels-Skyland-Hideaway-Mountain-Cabin-W-Hot-Tub.h87568647.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/114000000/113310000/113303900/113303853/f58c744e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113310000/113303900/113303853/77e9513a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113310000/113303900/113303853/7d8a7274.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/113310000/113303900/113303853/w1280h864x0y96-3ee7358b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Foxwood Cabin | Hot Tub, Screened Porch, Grill Front Royal 10/10 Exceptional (5) "Our stay was positively excellent. The property was extremely well-kept and clean. The king bed was so comfortable, and the master bedroom was magical. The hot tub was the icing on the cake, and the views were stunning. I would recommend this property to anyone looking to get away from the hustle and bustle of every day living." CA $258 CA $623 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Front-Royal-Hotels-The-Foxwood-Cabin-Hot-Tub.h113303853.Hotel-Information) ![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/96000000/95050000/95042500/95042415/w904h683x60y0-64dd4a06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95050000/95042500/95042415/w905h683x59y0-b8703cd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels, soap, shampoo](https://images.trvl-media.com/lodging/96000000/95050000/95042500/95042415/w424h683x300y0-9f1b99bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/96000000/95050000/95042500/95042415/w301h683x362y0-6f04a930.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg. Middleburg 9.8/10 Exceptional (17) "Pamela was wonderful to work with and the loft was so cute!" CA $210 CA $383 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Middleburg-Hotels-Cosy-Studio-On-An-Organic-Farm.h95042415.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/119000000/118100000/118097900/118097810/48866a9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118100000/118097900/118097810/fb88912d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave](https://images.trvl-media.com/lodging/119000000/118100000/118097900/118097810/fe01edb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/119000000/118100000/118097900/118097810/c4d6d514.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 1-bedroom apartment in Old Town Warrenton, walkable to Main Street Warrenton 10/10 Exceptional (3) "Clean, cute, hot water, cool inside. I would stay again!!!" CA $231 CA $374 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Warrenton-Hotels-Charming-1-Bedroom-Apartment-In-Old-Town-Warrenton.h118097810.Hotel-Information) ![Living area](https://images.trvl-media.com/lodging/108000000/107900000/107895800/107895789/w1117h810x5y0-b88c2c12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107900000/107895800/107895789/288bbbf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/108000000/107900000/107895800/107895789/w1025h1046x4y3-ad71c285.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107900000/107895800/107895789/0da8d534.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Morocco Loft 2BR overlooking city walking mall Old Town Winchester 10/10 Exceptional (2) "Great property with all the comforts of home" CA $249 CA $446 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Winchester-Hotels-Morocco-Loft-2BR-Overlooking-City-Walking-Mall.h107895789.Hotel-Information) ![Apartment (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/113000000/112530000/112522800/112522717/ecd62a5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/113000000/112530000/112522800/112522717/10ab8517.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/113000000/112530000/112522800/112522717/f5585755.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/113000000/112530000/112522800/112522717/73607a0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Balcony & Pool Access: Modern Gainesville Home Gainesville CA $226 CA $620 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Gainesville-Hotels-Balcony-Pool-Access-Modern-Gainesville-Home.h112522717.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/76000000/75860000/75853900/75853887/11bbc02b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/76000000/75860000/75853900/75853887/81902a90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/76000000/75860000/75853900/75853887/9e695565.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/76000000/75860000/75853900/75853887/1984db96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Blue Door steps from Handley Library Old Town Winchester 7.0/10 Good (2) "Perfect. Met all expectations. Small but Great." CA $161 CA $270 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Winchester-Hotels-The-Blue-Door-Steps-From-Handley-Library.h75853887.Hotel-Information) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/76000000/75860000/75852300/75852258/434367ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/76000000/75860000/75852300/75852258/ace40b05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/76000000/75860000/75852300/75852258/2359633a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75860000/75852300/75852258/b00d8fd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Nostalgia Lane in the heart of the city Old Town Winchester 8.8/10 Excellent (13) "Great location in the heart of Winchester. Walking distance to everything. " CA $259 CA $454 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Winchester-Hotels-Nostalgia-Lane-In-The-Heart-Of-The-City.h75852258.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75860000/75856800/75856721/765a953b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/76000000/75860000/75856800/75856721/85465173.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/76000000/75860000/75856800/75856721/f2a89cc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/76000000/75860000/75856800/75856721/547de25c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Yellow Submarine trendy basement apt and courtyard Old Town Winchester 9.0/10 Wonderful (2) "Very clean and comfortable. Really cool furniture pieces. Nice kitchen, dining room, living room. Will stay here again when in the area. " CA $204 CA $363 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Winchester-Hotels-Yellow-Submarine-Trendy-Basement-Apt-Wcourtyard.h75856721.Hotel-Information) ![2 bedrooms, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120420000/120414100/120414068/7c5e3f89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120420000/120414100/120414068/5da0117c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/121000000/120420000/120414100/120414068/d0053ed9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/121000000/120420000/120414100/120414068/b0af47e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW! Historic Schoolhouse HotTub+FirePit+Wineries Fauquier County CA $155 CA $486 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Linden-Hotels-NEW-Historic-Schoolhouse-HotTubFirePitWineries.h120414068.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/114000000/113030000/113027300/113027243/17745535.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113030000/113027300/113027243/9b7a2bda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113030000/113027300/113027243/0bb76882.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/114000000/113030000/113027300/113027243/a1533d00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Honeymoon Cabin | Private Retreat w/ hot tub Front Royal CA $182 CA $513 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Front-Royal-Hotels-The-Honeymoon-Cabin-Private-Retreat-W-Hot-Tub.h113027243.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/76000000/75860000/75856500/75856493/80b59f6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/76000000/75860000/75856500/75856493/31a46244.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/76000000/75860000/75856500/75856493/2c3dcc54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/76000000/75860000/75856500/75856493/w1413h1055x0y0-6561893b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### WonderClock House downtown vintage duplex w/ porches, steps to Handley Library Old Town Winchester 9.0/10 Wonderful (6) "Our Wonder Clock stay was great. Everything was as expected. Location to downtown was awesome and very easily walkable. Our stay was cut short unexpectedly, but we would stay here again! The host was very responsive to one concern we had and was willing to fix immediately. " CA $287 CA $511 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Winchester-Hotels-WonderClock-House-Downtown-Vintage-Duplex-W-Porches.h75856493.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=2025-10-27&endDate=2025-10-28®ionId=184116&adults=2&lodging=APARTMENT&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-Apartments.d184116-aaApartments.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FUpperville-Apartments.d184116-aaApartments.Travel-Guide-Accommodation) ## Top Upperville Hotel Reviews ![Hampton Inn Winchester-University/Mall Area](//images.trvl-media.com/lodging/1000000/20000/20000/19971/17b0fc68_y.jpg) ### Hampton Inn Winchester-University/Mall Area 10/10 Excellent "Great stay! Would definitely would stay again!" [](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.Hotel-Information) ![Hilton Garden Inn Dulles North](//images.trvl-media.com/lodging/3000000/2340000/2335200/2335184/b8108f6b_y.jpg) ### Hilton Garden Inn Dulles North 10/10 Excellent "This hotel was a little dated but very clean. The bathroom was very nice. I loved the shower area. But only issue was it water was leaking into the main floor thru the crack while I was taking shower." [](https://expedia.ca/Ashburn-Hotels-Hilton-Garden-Inn-Dulles-North.h2335184.Hotel-Information) ![Travelodge by Wyndham Winchester](//images.trvl-media.com/lodging/1000000/10000/9600/9600/28616e5b_y.jpg) ### Travelodge by Wyndham Winchester 10/10 Excellent "I love this place. Very clean. I've been to many motels in the area and they are horrible, filthy, unkempt properties. Here they have an elevator which is very easy on the legs and arms when getting one's luggage in. Very congenial owner. They don't discriminate against smokers. Other motels in the area put a smoker in rooms that weren't even cleaned. I would recommend this Travel Lodge to all types of guests. Business or leisure." [](https://expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ![Country Inn & Suites by Radisson, Winchester, VA](//images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/d0690cde_y.jpg) ### Country Inn & Suites by Radisson, Winchester, VA 10/10 Excellent "Perfect stop over on our road trip. Clean with friendly staff. Breakfast was great with waffle machines!" [](https://expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) ![Days Inn by Wyndham Charles Town/Harpers Ferry](//images.trvl-media.com/lodging/11000000/10630000/10620700/10620696/6feea908_y.jpg) ### Days Inn by Wyndham Charles Town/Harpers Ferry 10/10 Excellent "Nice place to stay" [](https://expedia.ca/Martinsburg-Hotels-Days-Inn-By-Wyndham-Charles-TownHarpers-Ferry.h10620696.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 10/10 Excellent "2 blocks from city hall/old town. Got married at city hall. Very easy and accessible and the hotel was beautiful. " [](https://expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![SpringHill Suites by Marriott Winchester](//images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/193cda05_y.jpg) ### SpringHill Suites by Marriott Winchester 10/10 Excellent "Convenient " [](https://expedia.ca/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Winchester](//images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb_y.jpg) ### La Quinta Inn & Suites by Wyndham Winchester 10/10 Excellent "Great location." [](https://expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Hotel Burg](//images.trvl-media.com/lodging/115000000/114280000/114275900/114275854/2337af83_y.jpg) ### Hotel Burg 10/10 Excellent "Very Friendly staff. The restaurant was very good, although the chef likes a bit of spice in all the food. " [](https://expedia.ca/Leesburg-Hotels-Hotel-Burg.h114275854.Hotel-Information) ## Find out more about Upperville ## Upperville Apartments information | Number of reviews | 180 | | --- | --- | | Accommodation | 77 Apartments | | Lowest Price | CA $246 | | Highest Price | CA $623 | ## Frequently asked questions ### What's it like to stay at an apartment in Upperville? > There are 6 lodging options in Upperville. Though there aren't many apartments, we can help you locate similar accommodations. When you search on Expedia, you can filter by amenities you might find in an apartment such as a kitchen. You can even filter by similar properties such as vacation homes, condos, or cabins. ### How do you know if an apartment is the best choice for you? > An apartment is often more spacious than a traditional hotel room and includes a kitchen, so you can have some home-cooked meals. Apartments are ideal for families who want the conveniences of home, and also for couples who want to stay away from the tourist areas. ### What's the top apartment for a stay in Upperville? > Below are some of the top apartments in the area: [Apple Mountain Retreat](https://www.expedia.ca/Linden-Hotels-Cozy-Spacious-Full-Basement-In-Single-Family-Home-On-Apple-Mountain.h104052857.Hotel-Information): Located in Linden, 13.2 mi/21.2 km from the heart of Upperville. Includes free WiFi, private patios, and fireplaces. Access to onsite laundry facilities is available on site. [Cozy 1BR Apt Minutes From Skyline Drive!!](https://www.expedia.ca/Amissville-Hotels-Cozy-1BR-Apt-Minutes-From-Skyline-Drive.h88519350.Hotel-Information): Located 21.8 mi/35.2 km away in Amissville. Free WiFi, private patios, and Smart TVs are included. Access to onsite laundry facilities is available on site. [Charming 2-Bedroom Basement Apartment with AC, WiFi in enchanting Leesburg](https://www.expedia.ca/Leesburg-Hotels-Charming-2-Bedroom-Apartment-With-AC.h115358469.Hotel-Information): Located in Leesburg, 19.2 mi/30.9 km away. Includes free WiFi, private patios, and Smart TVs. Onsite laundry facilities and a sauna are on site. [Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.](https://www.expedia.ca/Bluemont-Hotels-Stylish-1-Bd1-Ba-Gardern-Apt-Within-Quaint-Bluemont-Village.h118716576.Hotel-Information): It's situated in Bluemont, 8.6 mi/13.8 km from Upperville. ### What can I expect from the weather in Upperville? > Though weather is just one factor, it can really affect your travel plans, especially when you're planning an extended stay in Upperville. The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 37°F. Average annual precipitation for Upperville is 44 inches. ### What are the must-see places to visit in Upperville? > Explore the area and family-friendly sights such as Great Country Farms, or get out into nature at a spot like Upperville Park. In the larger area, you'll find Sky Meadows State Park and Delaplane Cellars. ### What's the best way to get to and around Upperville? > Knowing a bit about the transportation options can save you time when you get to your destination. Fly into Washington Dulles Intl. Airport (IAD), which is located 23.7 mi (38.2 km) away from the city center. Otherwise, look for flights into Manassas, VA (MNZ-Manassas Regional), which is 27.3 mi (44 km) away. 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