Title: 10 Best Hotels in Winchester Historic District, Winchester for 2026 | 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) ![A nice 3 block outdoor downtown shopping area with dining and bars also. ](https://images.trvl-media.com/place/6056879/3acc501a-a330-4063-b538-b2368ef6a4c5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Fernando Begay # 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 ## Go beyond your typical stay in Winchester Historic District Family friendly [](https://www.expedia.ca/Hotel-Search?destination=Winchester+Historic+District%2C+Winchester%2C+Virginia%2C+United+States+of+America®ionId=918789051029594112&latLong=39.184877%2C-78.167913&adults=2&startDate=2025-12-28&d1=2025-12-28&endDate=2025-12-30&d2=2025-12-30&travelerType=family_friendly) Cabin [](https://www.expedia.ca/Hotel-Search?destination=Winchester+Historic+District%2C+Winchester%2C+Virginia%2C+United+States+of+America®ionId=918789051029594112&latLong=39.184877%2C-78.167913&adults=2&startDate=2025-12-28&d1=2025-12-28&endDate=2025-12-30&d2=2025-12-30&lodging=CABIN) Pool [](https://www.expedia.ca/Hotel-Search?destination=Winchester+Historic+District%2C+Winchester%2C+Virginia%2C+United+States+of+America®ionId=918789051029594112&latLong=39.184877%2C-78.167913&adults=2&startDate=2025-12-28&d1=2025-12-28&endDate=2025-12-30&d2=2025-12-30&amenities=POOL) Hot tub [](https://www.expedia.ca/Hotel-Search?destination=Winchester+Historic+District%2C+Winchester%2C+Virginia%2C+United+States+of+America®ionId=918789051029594112&latLong=39.184877%2C-78.167913&adults=2&startDate=2025-12-28&d1=2025-12-28&endDate=2025-12-30&d2=2025-12-30&amenities=HOT_TUB) Pet friendly [](https://www.expedia.ca/Hotel-Search?destination=Winchester+Historic+District%2C+Winchester%2C+Virginia%2C+United+States+of+America®ionId=918789051029594112&latLong=39.184877%2C-78.167913&adults=2&startDate=2025-12-28&d1=2025-12-28&endDate=2025-12-30&d2=2025-12-30&amenities=PETS) Apart­ment [](https://www.expedia.ca/Hotel-Search?destination=Winchester+Historic+District%2C+Winchester%2C+Virginia%2C+United+States+of+America®ionId=918789051029594112&latLong=39.184877%2C-78.167913&adults=2&startDate=2025-12-28&d1=2025-12-28&endDate=2025-12-30&d2=2025-12-30&lodging=APARTMENT) Cottage [](https://www.expedia.ca/Hotel-Search?destination=Winchester+Historic+District%2C+Winchester%2C+Virginia%2C+United+States+of+America®ionId=918789051029594112&latLong=39.184877%2C-78.167913&adults=2&startDate=2025-12-28&d1=2025-12-28&endDate=2025-12-30&d2=2025-12-30&lodging=COTTAGE) ## Check prices for these dates Tonight [Dec 14 - Dec 15](https://www.expedia.ca/Hotel-Search?regionId=918789051029594112&startDate=2025-12-14&endDate=2025-12-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 15 - Dec 16](https://www.expedia.ca/Hotel-Search?regionId=918789051029594112&startDate=2025-12-15&endDate=2025-12-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=918789051029594112&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=918789051029594112&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Recommended Price (low to high) Distance Star rating ## Our top choices for Winchester Historic District hotels ![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) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/50dde1f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/31f87045.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) ### The George Washington Hotel, A Wyndham Grand Hotel [](https://www.expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) Winchester Historic District 9.4/10 Exceptional (1008) "Great hotel!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) CHARLES CA $174 CA $198 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/3eaf7092.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/5447905f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/e8922549.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Microtel Inn & Suites by Wyndham Winchester [](https://www.expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information) 4.2 km from Winchester Historic District 9.2/10 Wonderful (1378) "Excellent accommodations" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Loretta CA $98 CA $107 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information) ![Snack bar](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/b9c1387b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/bf8dce02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/25562c26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/40000000/39500000/39493500/39493421/e84bf2ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### TRU By Hilton Winchester [](https://www.expedia.ca/Winchester-Hotels-TRU-By-Hilton-Winchester.h39493421.Hotel-Information) 4.4 km from Winchester Historic District 9.0/10 Wonderful (766) "The hotel was clean and the staff was pleasant." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sherri CA $98 CA $107 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Winchester-Hotels-TRU-By-Hilton-Winchester.h39493421.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/cf4c2663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/8506bf92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily self-serve breakfast](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/c6c8c1e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/557f4fea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Winchester [](https://www.expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information) 7.8 km from Winchester Historic District 9.4/10 Exceptional (1075) "Very clean, helpful staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathleen CA $135 CA $147 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/11000000/10630000/10620700/10620696/cb7df1a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free self parking](https://images.trvl-media.com/lodging/11000000/10630000/10620700/10620696/20c409c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/11000000/10630000/10620700/10620696/5a90060e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/11000000/10630000/10620700/10620696/9b09e95c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Days Inn by Wyndham Charles Town/Harpers Ferry [](https://www.expedia.ca/Martinsburg-Hotels-Days-Inn-By-Wyndham-Charles-TownHarpers-Ferry.h10620696.Hotel-Information) 29.7 km from Winchester Historic District 8.0/10 Very good (1003) "The room is clean. The staff is friendly. The breakfast was good. No-frills hotel, but clean and efficient. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelsey CA $91 CA $102 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Martinsburg-Hotels-Days-Inn-By-Wyndham-Charles-TownHarpers-Ferry.h10620696.Hotel-Information) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/9e66afda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb.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) ![Fitness facility](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/d8a75afe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Winchester [](https://www.expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) 3 km from Winchester Historic District 9.2/10 Wonderful (2225) "Rooms are always clean when I stay and the staff was very friendly. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ashley CA $140 CA $152 total includes taxes & fees Jan 12 - Jan 13, 2026 [](https://www.expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/ac575b89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/b2c1f0d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/4baca37a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/1000000/120000/117800/117743/cd7ad69b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spark by Hilton Winchester [](https://www.expedia.ca/Winchester-Hotels-Spark-By-Hilton-Winchester.h117743.Hotel-Information) 2.1 km from Winchester Historic District 9.0/10 Wonderful (1002) "Great location close to restaurants " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) SILVIA CA $104 CA $117 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Winchester-Hotels-Spark-By-Hilton-Winchester.h117743.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/3000000/2770000/2762700/2762649/30ef090b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Check-in/check-out kiosk](https://images.trvl-media.com/lodging/3000000/2770000/2762700/2762649/0f03a335.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/3000000/2770000/2762700/2762649/6f99e56e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/3000000/2770000/2762700/2762649/52d84062.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Carriage Inn B&B [](https://www.expedia.ca/Martinsburg-Hotels-The-Carriage-Inn-BB.h2762649.Hotel-Information) 29.4 km from Winchester Historic District 9.6/10 Exceptional (439) "Excellent accommodations and breakfast. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William CA $177 CA $201 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Martinsburg-Hotels-The-Carriage-Inn-BB.h2762649.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/810f7f7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/40efde4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/54c3ac5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch LCD TV with cable channels, TV](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/6c4fd659.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Front Royal [](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.Hotel-Information) 25.1 km from Winchester Historic District 9.0/10 Wonderful (1002) "Room was spotless, place was quiet and our welcome at the desk was perfect" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Merrill CA $148 CA $164 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/a391dd61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/f49e1754.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/6b04791b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/b42e7086.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Inn & Suites by Radisson, Winchester, VA [](https://www.expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) 7.5 km from Winchester Historic District 8.8/10 Excellent (1002) "Have stayed here multiple times -always good" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $115 CA $125 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) ![2 bars/lounges, sports bar](https://images.trvl-media.com/lodging/10000000/9870000/9868900/9868848/9a1a11fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Casino](https://images.trvl-media.com/lodging/10000000/9870000/9868900/9868848/b511b890.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/10000000/9870000/9868900/9868848/ab154d36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/10000000/9870000/9868900/9868848/64e72433.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rodeway Inn & Suites Charles Town [](https://www.expedia.ca/Martinsburg-Hotels-Rodeway-Inn-Suites.h9868848.Hotel-Information) 29.9 km from Winchester Historic District 8.6/10 Excellent (1005) "Certainly will stay again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) philip CA $88 CA $99 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Martinsburg-Hotels-Rodeway-Inn-Suites.h9868848.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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/7ff8d7be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/d236d605.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Winchester Se-Historic Gateway by IHG [](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information) 3.3 km from Winchester Historic District 9.0/10 Wonderful (1003) "Clean room, quiet area, good breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laurie CA $96 CA $109 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/77000000/76880000/76876900/76876848/6291b142.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/77000000/76880000/76876900/76876848/cb927ccc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Casino](https://images.trvl-media.com/lodging/77000000/76880000/76876900/76876848/61b207d7.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) ### The Inn at Charles Town - Hollywood Casino [](https://www.expedia.ca/Charles-Town-Hotels-The-Inn-At-Charles-Town.h76876848.Hotel-Information) 30.2 km from Winchester Historic District 8.6/10 Excellent (523) "Friendly staff, comfortable bed, convenient location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kourtney CA $179 CA $214 total includes taxes & fees Dec 30 - Dec 31 [](https://www.expedia.ca/Charles-Town-Hotels-The-Inn-At-Charles-Town.h76876848.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/860000/855600/855557/10b5cc1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/860000/855600/855557/d565eb6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/860000/855600/855557/4749606b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/860000/855600/855557/a71565c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super 8 by Wyndham Front Royal [](https://www.expedia.ca/Winchester-Hotels-Super-8-By-Wyndham-Front-Royal.h855557.Hotel-Information) 30.4 km from Winchester Historic District 7.6/10 Good (1006) "The staff was friendly and attentive. The room was clean. The breakfast was good, with pancakes, toast, cereal, juice, and coffee. Good location for visiting Shenandoah National Park." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Teresa CA $85 CA $95 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Winchester-Hotels-Super-8-By-Wyndham-Front-Royal.h855557.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/c93a366a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/8a97ffc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/e6dc1dff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pillowtop beds, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/67555e67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SpringHill Suites by Marriott Winchester [](https://www.expedia.ca/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information) 5.3 km from Winchester Historic District 9.4/10 Exceptional (779) "The staff were friendly and knowledgeable . Clean room and breakfast was excellent. Hotel close to restaurants and stores. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Yolanda CA $148 CA $160 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/40000/34400/34394/83ee60b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually furnished, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/40000/34400/34394/fde0973a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free buffet breakfast](https://images.trvl-media.com/lodging/1000000/40000/34400/34394/ef7d5b18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/40000/34400/34394/cb88e2d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Winchester South-Stephens City by IHG [](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Express-Winchester-South-Stephens-City.h34394.Hotel-Information) 12.5 km from Winchester Historic District 8.2/10 Very good (802) "Nice stay and friendly people " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ALFRED CA $102 CA $111 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Winchester-Hotels-Holiday-Inn-Express-Winchester-South-Stephens-City.h34394.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/204cbf3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/d92b1c53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/9cf3d079.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889081/9874bc44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Front Royal Blue Ridge Shadows [](https://www.expedia.ca/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.Hotel-Information) 22 km from Winchester Historic District 9.0/10 Wonderful (1002) "Friendly staff, nice clean room, hotel restaurant was delicious. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dorothy CA $134 CA $148 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Front-Royal-Hotels-Holiday-Inn-Suites-Front-Royal-Blue-Ridge-Shadows.h1889081.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/4000000/3090000/3082200/3082115/7b9d69e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (The Overlook)](https://images.trvl-media.com/lodging/4000000/3090000/3082200/3082115/8ab65f08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Food and drink](https://images.trvl-media.com/lodging/4000000/3090000/3082200/3082115/80e06b30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (The Snuggery)](https://images.trvl-media.com/lodging/4000000/3090000/3082200/3082115/af2498b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hillbrook Inn [](https://www.expedia.ca/Martinsburg-Hotels-Hillbrook-Inn.h3082115.Hotel-Information) 21.8 km from Winchester Historic District 8.6/10 Excellent (671) "We had a wonderful time at Hillbrook. Loved the grounds, the cozy room, the spa massage was awesome!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nataliya CA $212 CA $272 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Martinsburg-Hotels-Hillbrook-Inn.h3082115.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/2fa2dbbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/0ec10473.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, 1 King Bed, Non Smoking, Refrigerator & Microwave (Wet bar)](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/5daa33ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/ca692cd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Winchester N/Conference Center, VA [](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-NConference-Center.h424883.Hotel-Information) 2.3 km from Winchester Historic District 9.2/10 Wonderful (846) "Super friendly reception and perfectly clean room. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dwight CA $142 CA $161 total includes taxes & fees Dec 20 - Dec 21 [](https://www.expedia.ca/Winchester-Hotels-Hampton-Inn-Winchester-NConference-Center.h424883.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) ![Suite, 1 Bedroom | Private kitchen](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652870/9604e34c.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) ![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652870/d39af4da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Candlewood Suites Winchester by IHG [](https://www.expedia.ca/Winchester-Hotels-Candlewood-Suites-Winchester.h1652870.Hotel-Information) 3.3 km from Winchester Historic District 8.8/10 Excellent (544) "Very clean room, excellent staff!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $107 CA $117 total includes taxes & fees Jan 3 - Jan 4, 2026 [](https://www.expedia.ca/Winchester-Hotels-Candlewood-Suites-Winchester.h1652870.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=2025-12-28&endDate=2025-12-29®ionId=918789051029594112&adults=2&sort=RECOMMENDED&openPlayBack=true) ## Where to stay in Winchester Historic District Find the best Winchester Historic District areas and neighborhoods for the activities you enjoy most. [Learn more about Winchester Historic District](https://www.expedia.ca/Winchester-Winchester-Historic-District.dx918789051029594112) - Old Town Winchester ![](https://mediaim.expedia.com/destination/1/720fb116634761161ecda43d4ca150e7.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [](https://www.expedia.ca/Hotel-Search?pwaOverlay=map®ionId=6164092) ![Old Town Winchester map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:_wcnFvob%7CMwb%40aMxGad%40bc%40pLeHpd%40&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=ljIi5EMaahlKlQ6KQ_BYkQvEIhQ=) ### Old Town Winchester Old Town Winchester is known for its ample dining options, and you can make a stop by Bright Box Theater and Shenandoah Valley Discovery Museum while in the area. [See properties](https://www.expedia.ca/Hotel-Search?regionId=6164092) ## Top Winchester Historic District Hotel Reviews ![Microtel Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657_y.jpg) ### Microtel Inn & Suites by Wyndham Winchester 10/10 Excellent "Clean nice room with a hot breakfast, a lot nicer then other places in Winchester especially for the price. Highly recommend " [](https://expedia.ca/Winchester-Hotels-Microtel-Inn-Suites-By-Wyndham-Winchester.h70921061.Hotel-Information) ![The George Washington Hotel, A Wyndham Grand Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5a07226c_y.jpg) ### The George Washington Hotel, A Wyndham Grand Hotel 10/10 Excellent "The room was clean and the bed was comfortable. My only desire is for firmer, foam pillows and brighter lights at the vanity. The staff is always efficient and friendly. It’s a beautiful hotel and we always have a good time at the bar!" [](https://expedia.ca/Winchester-Hotels-The-George-Washington-Hotel.h1364026.Hotel-Information) ![Hampton Inn Front Royal](https://images.trvl-media.com/lodging/1000000/900000/892600/892585/737257e0_y.jpg) ### Hampton Inn Front Royal 10/10 Excellent "All great " [](https://expedia.ca/Winchester-Hotels-Hampton-Inn-Front-Royal.h892585.Hotel-Information) ![SpringHill Suites by Marriott Winchester](https://images.trvl-media.com/lodging/43000000/42550000/42543800/42543772/193cda05_y.jpg) ### SpringHill Suites by Marriott Winchester 10/10 Excellent "Clean room , wonderful front staff. Gave concise advice about directions and what to do" [](https://expedia.ca/Winchester-Hotels-SpringHill-Suites-By-Marriott-Winchester.h42543772.Hotel-Information) ![Holiday Inn Winchester Se-Historic Gateway by IHG](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/c68804b2_y.jpg) ### Holiday Inn Winchester Se-Historic Gateway by IHG 10/10 Excellent "Clean room, quiet area, good breakfast" [](https://expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester-Se-Historic-Gateway.h1889084.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb_y.jpg) ### La Quinta Inn & Suites by Wyndham Winchester 10/10 Excellent "Comfortable and clean room." [](https://expedia.ca/Winchester-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Winchester.h2678524.Hotel-Information) ![Country Inn & Suites by Radisson, Winchester, VA](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/d0690cde_y.jpg) ### Country Inn & Suites by Radisson, Winchester, VA 10/10 Excellent "Room was large, very clean and very comfortable." [](https://expedia.ca/Winchester-Hotels-Country-Inn-Suites-By-Radisson.h1652833.Hotel-Information) ![Travelodge by Wyndham Winchester](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/9d44a9b1_y.jpg) ### Travelodge by Wyndham Winchester 10/10 Excellent "Room clean, heater works great parking " [](https://expedia.ca/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) ![Comfort Inn & Suites Winchester](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/cf4c2663_y.jpg) ### Comfort Inn & Suites Winchester 10/10 Excellent "Great accomodations!!" [](https://expedia.ca/Winchester-Hotels-Comfort-Inn-Suites.h57958244.Hotel-Information) ## Frequently asked questions ### What's it like in Winchester Historic District? ### Where is the best hotel for a stay in Winchester Historic District? ### How many hotels can I expect to find in Winchester Historic District? ### If I need to cancel my hotel reservation in Winchester Historic District, will I receive a refund? ### What is there to do around this Winchester neighborhood? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [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 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) - [Hotels near Blue Ridge Shadows Golf Club ](https://www.expedia.ca/Blue-Ridge-Shadows-Golf-Club-Hotels.0-l553248621532661832-0.Travel-Guide-Filter-Hotels) - [Boyce Hotels ](https://www.expedia.ca/Boyce-Hotels.d184084.Travel-Guide-Hotels) - [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) - [Cross Junction Hotels ](https://www.expedia.ca/Cross-Junction-Hotels.d553248635975978078.Travel-Guide-Hotels) - [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) - [Gore Hotels ](https://www.expedia.ca/Gore-Hotels.d3000460015.Travel-Guide-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) - [Middletown Hotels ](https://www.expedia.ca/Middletown-Hotels.d12013.Travel-Guide-Hotels) - [Millwood Hotels ](https://www.expedia.ca/Millwood-Hotels.d3000460156.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) - [Riverton Hotels ](https://www.expedia.ca/Riverton-Hotels.d553248635975849884.Travel-Guide-Hotels) - [Hotels near Rock Harbor Golf Course ](https://www.expedia.ca/Rock-Harbor-Golf-Course-Hotels.0-l553248621561864838-0.Travel-Guide-Filter-Hotels) - [Hotels near Shenandoah River ](https://www.expedia.ca/Shenandoah-River-Hotels.0-l681974697590321152-0.Travel-Guide-Filter-Hotels) - [Hotels near Shenandoah University ](https://www.expedia.ca/Shenandoah-University-Hotels.0-l6127311-0.Travel-Guide-Filter-Hotels) - [Star Tannery Hotels ](https://www.expedia.ca/Star-Tannery-Hotels.d3000460674.Travel-Guide-Hotels) - [Hotels near State Arboretum of Virginia ](https://www.expedia.ca/State-Arboretum-Of-Virginia-Hotels.0-l6164038-0.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) - [Hotels near Watermelon Park Campground ](https://www.expedia.ca/Watermelon-Park-Campground-Hotels.0-l553248621532661928-0.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 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) - [Book Hotels in Winchester Historic District on Expedia.com ](https://www.expedia.com/Winchester-Historic-District-Winchester-Hotels.0-n918789051029594112-0.Travel-Guide-Filter-Hotels)