Title: Book the Best Winchester Historic District LUXURY Hotels - Upscale Hotels in Winchester Historic District, Winchester | 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 Luxury Hotels in Winchester Historic District, Winchester ![](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 Luxury Hotels Tonight [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=918789051029594112&startDate=2025-10-13&endDate=2025-10-14&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=918789051029594112&startDate=2025-10-14&endDate=2025-10-15&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=918789051029594112&startDate=2025-10-17&endDate=2025-10-19&adults=2&propertyStyle=LUXURY&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&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winchester Historic District Luxury Hotels ## Top Winchester Historic District Hotel Reviews ![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 "Was just one night with group of friends. Location was great, easy check in and out, good breakfast and comfy beds. Would highly recommend. " [](https://expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Rodeway Inn & Suites - Charles Town, WV](//images.trvl-media.com/lodging/10000000/9870000/9868900/9868848/b6dd3662_y.jpg) ### Rodeway Inn & Suites - Charles Town, WV 10/10 Excellent "Fast check in" [](https://expedia.ca/Martinsburg-Hotels-Rodeway-Inn-Suites.h9868848.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 10/10 Excellent "Great stay! Would definitely would stay again!" [](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 "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) ![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 "Very nice hotel " [](https://expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.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 "Area " [](https://expedia.ca/Winchester-Hotels-Super-8-By-Wyndham-Front-Royal.h855557.Hotel-Information) ## Frequently asked questions ### Are you looking for a luxury hotel for your stay in Winchester Historic District? > Use Expedia to help you arrange a flight to Martinsburg, WV (MRB-Eastern West Virginia Regional) airport or Washington Dulles Intl. Airport (IAD) airport, and then choose from a variety of places to stay that will deliver the luxury you want. Amenities are an important consideration when you plan a trip, so we make it easy to get what you need to make your stay special. If you want a posh hotel with fine dining, a spa, or several swimming pools, Expedia can assist you in finding the best luxury hotel experience that Winchester Historic District has to offer. Winchester Historic District has some interesting things to see and do including Bright Box Theater and Winchester Little Theater, so you might want to take in the local sights during your visit. ### What's there to see and do in Winchester Historic District? > When you're in Winchester Historic District, enjoy exploring the sights and attractions here including Bright Box Theater, Winchester Little Theater, and Shenandoah Valley Discovery Museum. If you have a little extra time during your trip, you might want to make a stop at Handley Regional Library and Stonewall Jackson's Headquarters. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - [3 Star Hotels in Old Town Winchester](https://www.expedia.ca/3Star-Old-Town-Winchester-Winchester-Hotels.s30-n6164092-0.Travel-Guide-Filter-Hotels) - [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) - [Berryville Hotels](https://www.expedia.ca/Berryville-Hotels.d184082.Travel-Guide-Hotels) - [Inns in Berryville](https://www.expedia.ca/Berryville-Inns.d184082-aaInns.Travel-Guide-Accommodation) - [Apartments in Boyce](https://www.expedia.ca/Boyce-Apartments.d184084-aaApartments.Travel-Guide-Accommodation) - [B&B in Boyce](https://www.expedia.ca/Boyce-Bed-And-Breakfast.d184084-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Boyce Hotels](https://www.expedia.ca/Boyce-Hotels.d184084.Travel-Guide-Hotels) - [Motels in Boyce](https://www.expedia.ca/Boyce-Motels.d184084-aaMotels.Travel-Guide-Accommodation) - [Hotels near Bright Box Theater](https://www.expedia.ca/Bright-Box-Theater-Hotels.0-l553248621561864843-0.Travel-Guide-Filter-Hotels) - [Motels in Brucetown](https://www.expedia.ca/Brucetown-Motels.d3000355042-aaMotels.Travel-Guide-Accommodation) - [Cheap Hotels in Clear Brook](https://www.expedia.ca/Clear-Brook-Hotels-Cheap-Hotels.0-0-d553248635975870250-tCheapHotels.Travel-Guide-Filter-Hotels) - [Clear Brook Hotels](https://www.expedia.ca/Clear-Brook-Hotels.d553248635975870250.Travel-Guide-Hotels) - [B&B in College Park](https://www.expedia.ca/College-Park-Bed-And-Breakfast.d553248635975870482-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Vacation Homes in College Park](https://www.expedia.ca/College-Park-Private-Vacation-Homes.d553248635975870482-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Hotels near Dinosaur Land](https://www.expedia.ca/Dinosaur-Land-Hotels.0-l553248621532661835-0.Travel-Guide-Filter-Hotels) - [B&B in Frederick County](https://www.expedia.ca/Frederick-County-Bed-And-Breakfast.d553248635976431672-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cottages in Frederick County](https://www.expedia.ca/Frederick-County-Cottages.d553248635976431672-aaCottages.Travel-Guide-Accommodation) - [Gainesboro Hotels](https://www.expedia.ca/Gainesboro-Hotels.d553248635976006643.Travel-Guide-Hotels) - [Hotels near George Washington's Office](https://www.expedia.ca/George-Washingtons-Office-Hotels.0-l6164042-0.Travel-Guide-Filter-Hotels) - [B&B in Jordan Springs](https://www.expedia.ca/Jordan-Springs-Bed-And-Breakfast.d553248635975872368-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cottages in Jordan Springs](https://www.expedia.ca/Jordan-Springs-Cottages.d553248635975872368-aaCottages.Travel-Guide-Accommodation) - [Villas in Jordan Springs](https://www.expedia.ca/Jordan-Springs-Villas.d553248635975872368-aaVillas.Travel-Guide-Accommodation) - [Luxury Hotels in Kernstown](https://www.expedia.ca/Kernstown-Hotels-Luxury-Hotel.0-0-d553248635975850140-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Kernstown Hotels](https://www.expedia.ca/Kernstown-Hotels.d553248635975850140.Travel-Guide-Hotels) - [Hotels near Mt Hebron Cemetery](https://www.expedia.ca/Mt-Hebron-Cemetery-Hotels.0-l553248621532661845-0.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Old Town Winchester](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Boutique-Hotel.0-n6164092-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Old Town Winchester](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Cheap-Hotels.0-n6164092-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Historic Hotels in Old Town Winchester](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Historic-Hotel.0-n6164092-0-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Hotels with Balconies in Old Town Winchester](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Hotels-With-Balconies.0-n6164092-0-tHotelswithBalconies.Travel-Guide-Filter-Hotels) - [Hotels with Free Breakfast in Old Town Winchester](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Hotels-With-Free-Breakfast.0-n6164092-0-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels) - [Hotels with Free Parking in Old Town Winchester](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Hotels-With-Free-Parking.0-n6164092-0-tHotelswithFreeParking.Travel-Guide-Filter-Hotels) - [Hotels with smoking rooms in Old Town Winchester](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Hotels-With-Smoking-Rooms.0-n6164092-0-tHotelswithsmokingrooms.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Old Town Winchester](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Luxury-Hotel.0-n6164092-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Old Town Winchester](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Pet-Friendly-Hotel.0-n6164092-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Old Town Winchester](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels-Spa-Hotel.0-n6164092-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Old Town Winchester Hotels](https://www.expedia.ca/Old-Town-Winchester-Winchester-Hotels.0-n6164092-0.Travel-Guide-Filter-Hotels) - [Hotels near Patsy Cline Historic House](https://www.expedia.ca/Patsy-Cline-Historic-House-Hotels.0-l553248621532661841-0.Travel-Guide-Filter-Hotels) - [Hotels near Rock Harbor Golf Course](https://www.expedia.ca/Rock-Harbor-Golf-Course-Hotels.0-l553248621561864838-0.Travel-Guide-Filter-Hotels) - [Cottages in Shawnee Land](https://www.expedia.ca/Shawnee-Land-Cottages.d553248635975849755-aaCottages.Travel-Guide-Accommodation) - [Hotels near Shenandoah University](https://www.expedia.ca/Shenandoah-University-Hotels.0-l6127311-0.Travel-Guide-Filter-Hotels) - [B&B in Stephens City](https://www.expedia.ca/Stephens-City-Bed-And-Breakfast.d12076-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Hotels & Resorts for Couples in Stephens City](https://www.expedia.ca/Stephens-City-Hotels-Couples-Resorts-Hotels.0-0-d12076-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Historic Hotels in Stephens City](https://www.expedia.ca/Stephens-City-Hotels-Historic-Hotel.0-0-d12076-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Stephens City Hotels](https://www.expedia.ca/Stephens-City-Hotels.d12076.Travel-Guide-Hotels) - [Hotels near Valerie Hill Winery](https://www.expedia.ca/Valerie-Hill-Winery-Hotels.0-l553248621532661834-0.Travel-Guide-Filter-Hotels) - [White Post Hotels](https://www.expedia.ca/White-Post-Hotels.d184119.Travel-Guide-Hotels) - [Apartments in Winchester](https://www.expedia.ca/Winchester-Apartments.d6056879-aaApartments.Travel-Guide-Accommodation) - [B&B in Winchester](https://www.expedia.ca/Winchester-Bed-And-Breakfast.d6056879-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cottages in Winchester](https://www.expedia.ca/Winchester-Cottages.d6056879-aaCottages.Travel-Guide-Accommodation) - [Hotels near Winchester-Frederick County Convention & Visitors Bureau](https://www.expedia.ca/Winchester-Frederick-County-Convention-Visitors-Bureau-Hotels.0-l553248621561864842-0.Travel-Guide-Filter-Hotels) - [Guest Houses in Winchester](https://www.expedia.ca/Winchester-Guest-Houses.d6056879-aaGuestHouses.Travel-Guide-Accommodation) - [Beach Hotel Hotels in Winchester](https://www.expedia.ca/Winchester-Hotels-Beach-Hotel.0-0-d6056879-tBeachHotel.Travel-Guide-Filter-Hotels) - [Best Western Hotels in Winchester](https://www.expedia.ca/Winchester-Hotels-Best-Western.0-0-d6056879--bBestWestern.Travel-Guide-Filter-Hotels) - [Casino Hotels in Winchester](https://www.expedia.ca/Winchester-Hotels-Casino-Hotel.0-0-d6056879-tCasinoHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Winchester](https://www.expedia.ca/Winchester-Hotels-Cheap-Hotels.0-0-d6056879-tCheapHotels.Travel-Guide-Filter-Hotels) - [Historic Hotels in Winchester](https://www.expedia.ca/Winchester-Hotels-Historic-Hotel.0-0-d6056879-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Hotels with Balconies in Winchester](https://www.expedia.ca/Winchester-Hotels-Hotels-With-Balconies.0-0-d6056879-tHotelswithBalconies.Travel-Guide-Filter-Hotels) - [Hotels with Free Breakfast in Winchester](https://www.expedia.ca/Winchester-Hotels-Hotels-With-Free-Breakfast.0-0-d6056879-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels) - [Hotels with Free Parking in Winchester](https://www.expedia.ca/Winchester-Hotels-Hotels-With-Free-Parking.0-0-d6056879-tHotelswithFreeParking.Travel-Guide-Filter-Hotels) - [Hotels with an Indoor Pool in Winchester](https://www.expedia.ca/Winchester-Hotels-Hotels-With-Indoor-Pool.0-0-d6056879-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels) - [Hotels with Kitchenettes in Winchester](https://www.expedia.ca/Winchester-Hotels-Hotels-With-Kitchenettes.0-0-d6056879-tHotelswithKitchenettes.Travel-Guide-Filter-Hotels) - [Hotels with smoking rooms in Winchester](https://www.expedia.ca/Winchester-Hotels-Hotels-With-Smoking-Rooms.0-0-d6056879-tHotelswithsmokingrooms.Travel-Guide-Filter-Hotels) - [Lgbt Friendly Hotels in Winchester](https://www.expedia.ca/Winchester-Hotels-LGBT-Friendly-Hotel.0-0-d6056879-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - [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)