Title: Visit Winchester Historic District: Best of Winchester Historic District, Winchester Travel 2025 | 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 top-notch restaurants or charming coffeehouses 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 top-notch restaurants or charming coffeehouses 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) #### 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) #### Stonewall Jackson's Headquarters Learn about the local history of Winchester when you take a trip to Stonewall Jackson's Headquarters. Check out the charming coffeehouses or top-notch restaurants in this walkable area. [](https://expedia.ca/Stonewall-Jacksons-Headquarters-Winchester.d6164032.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 $177 CA $200 total Oct 9 - Oct 10 includes taxes & fees Stay at this 3.5-star spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the bar and the helpful staff in our ... 9.2/10 Wonderful! (1,000 reviews) "The beauty of the property to begin with. Old world charm but modernized without detracting from the original character. The grand mailbox, each floor having a mailbox which directly connects with and is fed by gravity to the “grand” collection box on the ground floor! Beautiful! The basement pool ..." Reviewed on Sep 24, 2025 [](https://expedia.ca/Hotel-Search?startDate=09%2F10%2F2025&endDate=10%2F10%2F2025&selected=1364026&PinnedHotelID=1364026&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 $136 CA $148 total Oct 26 - Oct 27 includes taxes & fees Stay at this 3-star 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! (2,158 reviews) "Convenient off I-81, clean, quiet,nice warm breakfast, even great dark roast coffee. Will definitely make this a stop on our way south annually" Reviewed on Oct 1, 2025 [](https://expedia.ca/Hotel-Search?startDate=26%2F10%2F2025&endDate=27%2F10%2F2025&selected=2678524&PinnedHotelID=2678524&HadPinnedHotel=true®ionId=918789051029594112) ![Hampton Inn Winchester-University/Mall Area](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/17b0fc68_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn Winchester-University/Mall Area 640 East Jubal Early Drive, Winchester, VA CA $148 CA $168 total Oct 13 - Oct 14 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! (1,014 reviews) "We needed a break with a long family care situation. We took a break and stayed in Winchester and relaxed. Hampton Inn was just perfect. Breakfast was great! Thank you!" Reviewed on Sep 28, 2025 [](https://expedia.ca/Hotel-Search?startDate=13%2F10%2F2025&endDate=14%2F10%2F2025&selected=19971&PinnedHotelID=19971&HadPinnedHotel=true®ionId=918789051029594112) ![Travelodge by Wyndham Winchester](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/28616e5b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Travelodge by Wyndham Winchester 160 Front Royal Pike, Winchester, VA CA $96 CA $105 total Nov 2 - Nov 3 includes taxes & fees Stay at this motel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in our reviews. ... 8.4/10 Very Good! (1,100 reviews) "Good no frills hotel for an overnight stay. Easy off/on Interstate. Room was clean, bed comfotable, breakfast fine (make your own waffles!), staff very friendly. We had a nice quiet night & would stay again." Reviewed on Sep 27, 2025 [](https://expedia.ca/Hotel-Search?startDate=02%2F11%2F2025&endDate=03%2F11%2F2025&selected=9600&PinnedHotelID=9600&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 Fully refundableReserve now, pay when you stay CA $108 CA $118 total Oct 31 - Nov 1 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! (1,353 reviews) "Great place with very cute rooms!!" Reviewed on Sep 29, 2025 [](https://expedia.ca/Hotel-Search?startDate=31%2F10%2F2025&endDate=01%2F11%2F2025&selected=70921061&PinnedHotelID=70921061&HadPinnedHotel=true®ionId=918789051029594112) ![Holiday Inn Winchester Se-Historic Gateway by IHG](https://images.trvl-media.com/lodging/2000000/1890000/1889100/1889084/c68804b2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn Winchester Se-Historic Gateway by IHG 333 Front Royal Pike, Winchester, VA CA $123 CA $138 total Nov 2 - Nov 3 includes taxes & fees Stay at this 3-star business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ... 9/10 Wonderful! (1,001 reviews) "The room was spacious." Reviewed on Oct 1, 2025 [](https://expedia.ca/Hotel-Search?startDate=02%2F11%2F2025&endDate=03%2F11%2F2025&selected=1889084&PinnedHotelID=1889084&HadPinnedHotel=true®ionId=918789051029594112) [See all 378 properties in Winchester Historic District](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=04%2F10%2F2025&endDate=05%2F10%2F2025®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 [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=918789051029594112&startDate=2025-10-03&endDate=2025-10-04) [Tonight](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=918789051029594112&startDate=2025-10-03&endDate=2025-10-04) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=918789051029594112&startDate=2025-10-03&endDate=2025-10-04) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=918789051029594112&startDate=2025-10-03&endDate=2025-10-04)[Oct 3 - Oct 4](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=918789051029594112&startDate=2025-10-03&endDate=2025-10-04) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=918789051029594112&startDate=2025-10-04&endDate=2025-10-05) [Tomorrow night](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=918789051029594112&startDate=2025-10-04&endDate=2025-10-05) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=918789051029594112&startDate=2025-10-04&endDate=2025-10-05) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=918789051029594112&startDate=2025-10-04&endDate=2025-10-05)[Oct 4 - Oct 5](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=918789051029594112&startDate=2025-10-04&endDate=2025-10-05) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=918789051029594112&startDate=03%2F10%2F2025&endDate=05%2F10%2F2025) [This weekend](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=918789051029594112&startDate=03%2F10%2F2025&endDate=05%2F10%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=918789051029594112&startDate=03%2F10%2F2025&endDate=05%2F10%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=918789051029594112&startDate=03%2F10%2F2025&endDate=05%2F10%2F2025)[Oct 3 - Oct 5](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=918789051029594112&startDate=03%2F10%2F2025&endDate=05%2F10%2F2025) * * * ### 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. [](https://expedia.ca/Winchester-Old-Town-Winchester.dx6164092) * * * * * * - [Stays](?pwaLob=wizard-hotel-pwa-v2) - [Packages](?pwaLob=wizard-package-pwa) - [Flights](?pwaLob=wizard-flight-pwa) - [Things to do](?pwaLob=wizard-lx-pwa) - [Cruises](?pwaLob=wizard-cruise-pwa) - [Cars](?pwaLob=wizard-car-pwa) # Winchester Historic District ## 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 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) - [Hotels near Bright Box Theater](https://www.expedia.ca/Bright-Box-Theater-Hotels.0-l553248621561864843-0.Travel-Guide-Filter-Hotels) - [B&B in College Park](https://www.expedia.ca/College-Park-Bed-And-Breakfast.d553248635975870482-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)