Title: Book the Best SHOPPING Hotels in Old Town Winchester in 2025 | Expedia.ca [Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d6056879.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.ca/Cheap-Flights-To-Winchester.d6056879.Travel-Guide-Flights)[Things to do in Winchester](https://expedia.ca/Things-To-Do-In-Winchester.d6056879.Travel-Guide-Activities)[Old Town Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Old-Town-Winchester.d6164092.Car-Rental-Guide)[Old Town Winchester Vacations](https://expedia.ca/Old-Town-Winchester.d6164092.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/720fb116634761161ecda43d4ca150e7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Shopping Hotels in Old Town Winchester, VA from CA $222 - ![](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 availability on Old Town Winchester Shopping Hotels Tonight [Nov 5 - Nov 6](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2025-11-05&endDate=2025-11-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 6 - Nov 7](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2025-11-06&endDate=2025-11-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=6164092&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Old Town Winchester Shopping Hotels ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/115000000/114350000/114349200/114349198/w905h683x59y0-9f28244e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/115000000/114350000/114349200/114349198/w905h683x60y0-4183e173.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/115000000/114350000/114349200/114349198/w905h683x60y0-c1839f94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114350000/114349200/114349198/07522565.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The River House Charles Town 10/10 Exceptional (9) "Excellent experience. Super clean house. Excellent location right on the river! Would definitely rent again!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Casey W. CA $161 CA $406 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Charles-Town-Hotels-The-River-House.h114349198.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/118000000/117740000/117735000/117734997/w2999h2002x1y1-de179e9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/118000000/117740000/117735000/117734997/w2998h2002x1y1-e4dac9a1.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/118000000/117740000/117735000/117734997/w2999h2002x0y1-34023d2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117740000/117735000/117734997/58d98b30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Welcome to the Ladybug Retreat! Boyce 10/10 Exceptional (1) "This home is lovely and the host has thought of everything. We will definitely stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Catherine A. CA $246 CA $569 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Paris-Hotels-Welcome-To-The-Ladybug-Retreat.h117734997.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/88000000/87550000/87542000/87541976/f93df358.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/88000000/87550000/87542000/87541976/fb9145f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, stereo](https://images.trvl-media.com/lodging/88000000/87550000/87542000/87541976/11a5455c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, stereo](https://images.trvl-media.com/lodging/88000000/87550000/87542000/87541976/36ca568c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Willow Suite ~ 1 of 5 Unique Stays at Basswood ~ Ground Floor, Ramp Access Capon Bridge 9.8/10 Exceptional (7) "Very nice accommodations. Really enjoyed our stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mark B. CA $122 CA $222 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Capon-Bridge-Hotels-Willow-Suite-1-Of-5-Unique-Stays-At-Basswood-Ground-Floor.h87541976.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/99000000/98500000/98495800/98495723/83125d77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/99000000/98500000/98495800/98495723/450f7eab.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/99000000/98500000/98495800/98495723/f36ecf04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/99000000/98500000/98495800/98495723/5879ce85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Little Red Schoolhouse Cross Junction 9.8/10 Exceptional (13) "We had a great time. Hot tub was nice and house was clean and well put together. Would stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joshua R. CA $96 CA $261 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Cross-Junction-Hotels-The-Little-Red-Schoolhouse.h98495723.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118930000/118929700/118929649/1520d4f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/119000000/118930000/118929700/118929649/cad5963c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118930000/118929700/118929649/88d4dc47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118930000/118929700/118929649/928d407e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain View Bungalow in Front Royal Front Royal 10/10 Exceptional (7) "Excelente propiedad " ![Mexico](https://a.travel-assets.com/egds/marks/flags/mx.svg) Miguel CA $190 CA $310 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Front-Royal-Hotels-Mountain-View-Bungalow-In-Front-Royal.h118929649.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=2025-11-19&endDate=2025-11-20®ionId=6164092&adults=2&location_highlights_explore=shopping&sort=RECOMMENDED&openPlayBack=true) ## Top Old Town Winchester 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 "good breakfast and service. room felt a bit cramped and tv did not work " [](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 10/10 Excellent "Clean. Comfortable. Nice staff. Breakfast was good. " [](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 "XXXX" [](https://expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.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 "very clean room" [](https://expedia.ca/Winchester-Hotels-Super-8-By-Wyndham-Front-Royal.h855557.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 "Service was great!!" [](https://expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.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 "We had a pleasant stay, staff was really nice and the room was spotless. Easy check in, the breakfast in the morning was enjoyable. " [](https://expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.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 "Staff were great. Beautiful property. Registration process was hampered by slow computers. Breakfast service was really slow at Houlihans " [](https://expedia.ca/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.Hotel-Information) ![Hampton Inn Front Royal](//images.trvl-media.com/lodging/1000000/900000/892600/892585/737257e0_y.jpg) ### Hampton Inn Front Royal 10/10 Excellent "The staff was amazing! As we zipped in and out we were always welcomed or wished a good day. Big smiles and just super nice! Loved the coffee/tea area. Talk about coming home. My one comment would be that the trash cans were never emptied in our room or bathroom. And because the cans are so small by end of day two they were overflowing. When the gal came to do our room we were just getting ready to leave and she said she couldn’t come in while guests were in the room. (Think that is a good safety concept for both her and guests.). So we told her we were leaving almost immediately and could she please empty our trash. Never came in as trash remained over flowing. When checking out Monday morning I mentioned this and the woman at the desk said “next time just put the trash outside your room in the hallway.” My comment is “When paying as much as was for stay of three nights - your trash cans should definitely be emptied!” All in all can not say enough about the quality and helpfulness of all the rest of the staff. Excellent group! " [](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.Hotel-Information) ![Candlewood Suites Winchester by IHG](//images.trvl-media.com/lodging/2000000/1660000/1652900/1652870/0a2d8398_y.jpg) ### Candlewood Suites Winchester by IHG 10/10 Excellent "Clean room friendly staff" [](https://expedia.ca/Winchester-Hotels-Candlewood-Suites-Winchester.h1652870.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - [4 Star Hotels in Stephens City](https://www.expedia.ca/4Star-Stephens-City-Hotels.s40-0-d12076.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Winchester](https://www.expedia.ca/4Star-Winchester-Hotels.s40-0-d6056879.Travel-Guide-Filter-Hotels) - [Hotels near Apple Blossom Mall](https://www.expedia.ca/Apple-Blossom-Mall-Hotels.0-l6164018-0.Travel-Guide-Filter-Hotels) - [Historic Hotels in Berryville](https://www.expedia.ca/Berryville-Hotels-Historic-Hotel.0-0-d184082-tHistoricHotel.Travel-Guide-Filter-Hotels) - 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[Motels in Winchester](https://www.expedia.ca/Winchester-Motels.d6056879-aaMotels.Travel-Guide-Accommodation) - [Flights to Boyce](https://www.expedia.ca/Cheap-Flights-To-Boyce.d184084.Travel-Guide-Flights) - [Flights to Millwood](https://www.expedia.ca/Cheap-Flights-To-Millwood.d3000460156.Travel-Guide-Flights) - [Flights to Winchester](https://www.expedia.ca/Cheap-Flights-To-Winchester.d6056879.Travel-Guide-Flights) - [Flights from Winchester Regional](https://www.expedia.ca/lp/airports/wgo/flights-from-winchester-regional-airport) - [Flights from Clear Brook](https://www.expedia.ca/lp/flights/553248635975870250/flights-from-clear-brook) - [Flights from Blacksburg (BCB) to Winchester (WGO)](https://www.expedia.ca/lp/flights/bcb/wgo/blacksburg-to-winchester) - [Flights from Hartford (BDL) to Winchester (WGO)](https://www.expedia.ca/lp/flights/bdl/wgo/hartford-to-winchester) - [Flights from Baltimore (BWI) to Winchester (WGO)](https://www.expedia.ca/lp/flights/bwi/wgo/baltimore-to-winchester) - [Flights from Denver (DEN) to Winchester (WGO)](https://www.expedia.ca/lp/flights/den/wgo/denver-to-winchester) - [Flights from Dallas (DFW) to Winchester (WGO)](https://www.expedia.ca/lp/flights/dfw/wgo/dallas-to-winchester) - [Flights from El Paso (ELP) to Winchester (WGO)](https://www.expedia.ca/lp/flights/elp/wgo/el-paso-to-winchester) - [Flights from Fort Lauderdale (FLL) to Winchester (WGO)](https://www.expedia.ca/lp/flights/fll/wgo/fort-lauderdale-to-winchester) - [Flights from Greenville (GSP) to Winchester (WGO)](https://www.expedia.ca/lp/flights/gsp/wgo/greenville-to-winchester) - [Flights from Jacksonville (JAX) to Winchester (WGO)](https://www.expedia.ca/lp/flights/jax/wgo/jacksonville-to-winchester) - [Flights from Melbourne (MEL) to Winchester (WGO)](https://www.expedia.ca/lp/flights/mel/wgo/melbourne-to-winchester) - [Flights from Sarasota (SRQ) to Winchester (WGO)](https://www.expedia.ca/lp/flights/srq/wgo/sarasota-to-winchester) - [Flights from Syracuse (SYR) to Winchester (WGO)](https://www.expedia.ca/lp/flights/syr/wgo/syracuse-to-winchester) - [Flights from Calgary (YYC) to Winchester (WGO)](https://www.expedia.ca/lp/flights/yyc/wgo/calgary-to-winchester) - [Flights from Toronto (YYZ) to Winchester (WGO)](https://www.expedia.ca/lp/flights/yyz/wgo/toronto-to-winchester) - [Appleland Sports Center](https://www.expedia.ca/Appleland-Sports-Center-Stephens-City.d553248621587477489.Vacation-Attraction) - [Jim Barnett Park](https://www.expedia.ca/Jim-Barnett-Park-Winchester.d6164028.Vacation-Attraction) - [Winchester Vacations](https://www.expedia.ca/Winchester.d6056879.Destination-Travel-Guides) - [Budget Rental Cars in Winchester](https://www.expedia.ca/Budget-Car-Rentals-In-Winchester.d6056879-c39.Car-Rental-Guide-Suppliers) - [Car rental Winchester](https://www.expedia.ca/Car-Rentals-In-Winchester.d6056879.Car-Rental-Guide) - [National Car Rental Rental Cars in Winchester](https://www.expedia.ca/National-Car-Rental-Car-Rentals-In-Winchester.d6056879-c42.Car-Rental-Guide-Suppliers) - [Winchester Vacation Rentals](https://www.expedia.ca/Winchester-Vacation-Rentals.d6056879.Travel-Guide-VacationRentals) - [Things to do in Winchester](https://www.expedia.ca/Things-To-Do-In-Winchester.d6056879.Travel-Guide-Activities)