Title: Book the Best ADVENTURE Hotels in Winchester Historic District in 2025 | Expedia.ca [Winchester Historic District Travel Guide](https://expedia.ca/Winchester-Winchester-Historic-District.dx918789051029594112)[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)[Winchester Historic District Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester-Historic-District.d918789051029594112.Car-Rental-Guide)[Winchester Historic District Vacations](https://expedia.ca/Winchester-Historic-District.d918789051029594112.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/720fb116634761161ecda43d4ca150e7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels & Resorts for Couples in Winchester Historic District, VA ![](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 Winchester Historic District Hotels & Resorts for Couples Tonight [Oct 19 - Oct 20](https://www.expedia.ca/Hotel-Search?regionId=918789051029594112&startDate=2025-10-19&endDate=2025-10-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 20 - Oct 21](https://www.expedia.ca/Hotel-Search?regionId=918789051029594112&startDate=2025-10-20&endDate=2025-10-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=918789051029594112&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=918789051029594112&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winchester Historic District Hotels & Resorts for Couples ![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) ![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) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/bff9ad76.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) ### The George Washington Hotel, A Wyndham Grand Hotel Old Town Winchester 9.4/10 Exceptional (1018) "Very nice hotel " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul CA $178 CA $201 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/737257e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/bb49c17d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/810f7f7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/afbe118c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Front Royal Front Royal 9.0/10 Wonderful (1015) "convenient to Shenandoah Park" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tariq CA $149 CA $166 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.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) ![Reception](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066410/27064e98.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) ![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) ### Fairfield Inn & Suites by Marriott Winchester Winchester 9.0/10 Wonderful (777) "Super friendly staff, clean rooms, very convenient. I would definitely stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathleen CA $130 CA $141 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Winchester-Hotels-Fairfield-Inn-Suites-By-Marriott-Winchester.h1066410.Hotel-Information) ![Snack bar](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/cba33bb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/be60c3ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/b2c8e1ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One king study sofabed non smoking](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/311c50f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Winchester N/Conference Center, VA Winchester 9.2/10 Wonderful (819) "Great place to stay. Super clean and comfortable beds." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roy Allen CA $148 CA $168 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-NConference-Center.h424883.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/17b0fc68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout drapes, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/a888dfb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/769f9c2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/16920465.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Winchester-University/Mall Area Winchester 9.0/10 Wonderful (1022) "Staff was excellent !!! Hotel was clean and comfortable in great location !!! Would stay here again !!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary CA $160 CA $181 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-UniversityMall-Area.h19971.Hotel-Information) ![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) ![Smart TV, books](https://images.trvl-media.com/lodging/115000000/114350000/114349200/114349198/w506h683x259y0-56e475a8.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) "Host communicated well. Great location right on the river. Family had a great time. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Geoff C. CA $175 CA $425 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Charles-Town-Hotels-The-River-House.h114349198.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) ![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) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/119000000/118930000/118929700/118929649/32a5f0df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain View Bungalow in Front Royal Front Royal 10/10 Exceptional (4) "Property was just what we were looking for " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tim C. CA $189 CA $309 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Front-Royal-Hotels-Mountain-View-Bungalow-In-Front-Royal.h118929649.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/119000000/118170000/118168400/118168351/50f1c901.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, travel crib, free WiFi](https://images.trvl-media.com/lodging/119000000/118170000/118168400/118168351/001a3838.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/119000000/118170000/118168400/118168351/0a85581d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/119000000/118170000/118168400/118168351/10bb3434.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Emberwood | Modern Chalet + Nature Spa + Trails, & Wineries Bluemont 10/10 Exceptional (1) "Perfect escape/getaway!!! Beautiful surroundings, beautiful decor and super clean. The home has everything available if you never want to leave the premises. Hot tub, sauna, cold plunge, fire pit, grill and Zen Den made this an easy decision to book. 5 Stars" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Allison K. CA $462 CA $967 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Bluemont-Hotels-Emberwood-Modern-Chalet-Nature-Spa-Trails.h118168351.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. 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[Luxury Hotels in Winchester](https://www.expedia.ca/Winchester-Hotels-Luxury-Hotel.0-0-d6056879-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Winchester](https://www.expedia.ca/Winchester-Hotels-Pet-Friendly-Hotel.0-0-d6056879-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Shopping Hotels in Winchester](https://www.expedia.ca/Winchester-Hotels-Shopping-Hotel.0-0-d6056879-tShoppingHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Winchester](https://www.expedia.ca/Winchester-Hotels-Spa-Hotel.0-0-d6056879-tSpaHotel.Travel-Guide-Filter-Hotels) - [Hotel Wedding Venues Hotels in Winchester](https://www.expedia.ca/Winchester-Hotels-Wedding-Hotels.0-0-d6056879-tWeddingHotels.Travel-Guide-Filter-Hotels) - [Winchester Hotels](https://www.expedia.ca/Winchester-Hotels.d6056879.Travel-Guide-Hotels) - [Inns in Winchester](https://www.expedia.ca/Winchester-Inns.d6056879-aaInns.Travel-Guide-Accommodation) - [Hotels near Winchester Medical Center](https://www.expedia.ca/Winchester-Medical-Center-Hotels.0-l6164057-0.Travel-Guide-Filter-Hotels) - [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 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)