Title: Visit Winchester Historic District: Best of Winchester Historic District, Winchester Travel 2026 | Expedia Tourism - Expedia.ca [Hotels in Winchester Historic District](https://expedia.ca/Winchester-Historic-District-Winchester-Hotels.0-n918789051029594112-0.Travel-Guide-Filter-Hotels)[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) # Winchester Historic District ## Winchester ![Winchester Historic District](https://mediaim.expedia.com/destination/1/720fb116634761161ecda43d4ca150e7.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Photo by Kelly Godby](https://mediaim.expedia.com/destination/2/297d683bf6c02958194b1942fe08aec5.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Kelly Godby](https://mediaim.expedia.com/destination/2/297d683bf6c02958194b1942fe08aec5.jpg) ![Photo by Kelly Godby](https://mediaim.expedia.com/destination/2/f49e8a63a13c776ab427323a5e49834e.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Kelly Godby](https://mediaim.expedia.com/destination/2/f49e8a63a13c776ab427323a5e49834e.jpg) ![Photo by Kelly Godby](https://mediaim.expedia.com/destination/2/6d3b3982724040fc8a572ddcf2811938.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Kelly Godby](https://mediaim.expedia.com/destination/2/6d3b3982724040fc8a572ddcf2811938.jpg) ![Photo by Kelly Godby](https://mediaim.expedia.com/destination/2/06546ed83b202fba84d0142ab0abdc43.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Kelly Godby](https://mediaim.expedia.com/destination/2/06546ed83b202fba84d0142ab0abdc43.jpg) ## Visit Winchester Historic District Things to do Hotels Where to stay [Winchester travel guide](https://expedia.ca/Winchester.dx6056879) --- ### Popular places to visit ![Handley Regional Library](https://mediaim.expedia.com/destination/2/73997bc29c1a471c7123089852c4944b.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Handley Regional Library 5/5(1 review) After visiting Handley Regional Library, make a plan to see the other sights and activities in Winchester. Check out the charming coffeehouses or top-notch restaurants in this walkable area. [](https://expedia.ca/Handley-Regional-Library-Old-Town-Winchester.d6164024.Vacation-Attraction) ![Museum of the Shenandoah Valley](https://mediaim.expedia.com/destination/2/00bcc1929a21a52154c279eaecdf93f9.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Museum of the Shenandoah Valley 5/5(1 review) You can spend time exploring the galleries in Museum of the Shenandoah Valley during your trip to Winchester. Check out the charming coffeehouses or top-notch restaurants in this walkable area. [](https://expedia.ca/Museum-Of-The-Shenandoah-Valley-Winchester.d6127313.Vacation-Attraction) #### Shenandoah Valley Discovery Museum You can take time to visit Shenandoah Valley Discovery Museum during your travels to Winchester. While in this walkable area, you can savor the top-notch restaurants. [](https://expedia.ca/Shenandoah-Valley-Discovery-Museum-Old-Town-Winchester.d553248621587527659.Vacation-Attraction) #### Bright Box Theater Enjoy a show at Bright Box Theater, a storied theater in Winchester. While in this walkable area, you can savor the top-notch restaurants. [](https://expedia.ca/Bright-Box-Theater-Old-Town-Winchester.d553248621561864843.Vacation-Attraction) #### Stonewall Jackson's Headquarters Learn about the local history of Winchester when you take a trip to Stonewall Jackson's Headquarters. Check out the top-notch restaurants or charming coffeehouses in this walkable area. [](https://expedia.ca/Stonewall-Jacksons-Headquarters-Winchester.d6164032.Vacation-Attraction) #### Winchester Little Theater Enjoy a show at Winchester Little Theater, a storied theater in Winchester. While in this walkable area, you can savor the top-notch restaurants. [](https://expedia.ca/Winchester-Little-Theater-Winchester.d6164047.Vacation-Attraction) --- ## Winchester Historic District Hotel Deals ![The George Washington Hotel, A Wyndham Grand Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5a07226c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The George Washington Hotel, A Wyndham Grand Hotel 103 E Piccadilly St Winchester VA CA $176 CA $199 total Jan 27 - Jan 28 includes taxes & fees Book a stay at this spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ... 9.2/10 Wonderful! (1,002 reviews) Staff was amazing! Benjamin and Carla are two of the kindest people ever! Reviewed on Jan 4, 2026 [](https://expedia.ca/Hotel-Search?startDate=27%2F01%2F2026&endDate=28%2F01%2F2026&selected=1364026&PinnedHotelID=1364026&HadPinnedHotel=true®ionId=918789051029594112) ![Microtel Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/71000000/70930000/70921100/70921061/fab1f657_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Microtel Inn & Suites by Wyndham Winchester 150 Faraday Plaza Winchester VA CA $113 CA $123 total Jan 26 - Jan 27 includes taxes & fees Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ... 9/10 Wonderful! (1,429 reviews) This is our number one spot to stay in in Winchester. The location is perfect. Rooms are clean and modern. Reviewed on Jan 14, 2026 [](https://expedia.ca/Hotel-Search?startDate=26%2F01%2F2026&endDate=27%2F01%2F2026&selected=70921061&PinnedHotelID=70921061&HadPinnedHotel=true®ionId=918789051029594112) ![La Quinta Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/3336c7bb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### La Quinta Inn & Suites by Wyndham Winchester 1055 Millwood Pike, Route 50 East Winchester VA CA $127 CA $139 total Jan 19 - Jan 20 includes taxes & fees Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ... 9.2/10 Wonderful! (2,242 reviews) Clean room; really comfortable bed. Great staff Reviewed on Jan 8, 2026 [](https://expedia.ca/Hotel-Search?startDate=19%2F01%2F2026&endDate=20%2F01%2F2026&selected=2678524&PinnedHotelID=2678524&HadPinnedHotel=true®ionId=918789051029594112) ![Travelodge by Wyndham Winchester](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/9d44a9b1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Travelodge by Wyndham Winchester 160 Front Royal Pike Winchester VA CA $94 CA $103 total Jan 28 - Jan 29 includes taxes & fees Stay at this motel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ... 8.4/10 Very Good! (1,086 reviews) C'était propre et tranquille Reviewed on Jan 11, 2026 [](https://expedia.ca/Hotel-Search?startDate=28%2F01%2F2026&endDate=29%2F01%2F2026&selected=9600&PinnedHotelID=9600&HadPinnedHotel=true®ionId=918789051029594112) ![Quality Inn Winchester](https://images.trvl-media.com/lodging/1000000/180000/172900/172810/0fd2f943_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Quality Inn Winchester 1601 Martinsburg Pike Winchester VA CA $117 CA $127 total Jan 23 - Jan 24 includes taxes & fees Stay at this hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ... 9.2/10 Wonderful! (1,002 reviews) Clean room, front dest service. Reviewed on Jan 5, 2026 [](https://expedia.ca/Hotel-Search?startDate=23%2F01%2F2026&endDate=24%2F01%2F2026&selected=172810&PinnedHotelID=172810&HadPinnedHotel=true®ionId=918789051029594112) ![Comfort Inn & Suites Winchester](https://images.trvl-media.com/lodging/58000000/57960000/57958300/57958244/cf4c2663_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Comfort Inn & Suites Winchester 195 Kernstown Commons Blvd Winchester VA CA $136 CA $148 total Jan 19 - Jan 20 includes taxes & fees Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ... 9.4/10 Exceptional! (1,092 reviews) Clean room Reviewed on Jan 9, 2026 [](https://expedia.ca/Hotel-Search?startDate=19%2F01%2F2026&endDate=20%2F01%2F2026&selected=57958244&PinnedHotelID=57958244&HadPinnedHotel=true®ionId=918789051029594112) [See all 376 properties in Winchester Historic District](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=17%2F01%2F2026&endDate=18%2F01%2F2026®ionId=918789051029594112) 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. ## Check Winchester Historic District hotel availability [Tonight ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=918789051029594112&startDate=2026-01-16&endDate=2026-01-17)[Jan 16 - Jan 17](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=918789051029594112&startDate=2026-01-16&endDate=2026-01-17) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=918789051029594112&startDate=2026-01-17&endDate=2026-01-18)[Jan 17 - Jan 18](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=918789051029594112&startDate=2026-01-17&endDate=2026-01-18) [This weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=918789051029594112&startDate=16%2F01%2F2026&endDate=18%2F01%2F2026)[Jan 16 - Jan 18](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=918789051029594112&startDate=16%2F01%2F2026&endDate=18%2F01%2F2026) --- ### Other neighbourhoods around Winchester Historic District ![Default Image](https://mediaim.expedia.com/destination/1/720fb116634761161ecda43d4ca150e7.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### 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. 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