Title: Visit Old Town Winchester: Best of Old Town Winchester, Winchester Travel 2025 | Expedia Tourism - Expedia.ca [Hotels in Old Town Winchester](https://expedia.ca/Old-Town-Winchester-Winchester-Hotels.0-n6164092-0.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)[Old Town Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Old-Town-Winchester.d6164092.Car-Rental-Guide)[Old Town Winchester Vacations](https://expedia.ca/Old-Town-Winchester.d6164092.Destination-Travel-Guides) # Old Town Winchester ## Winchester ![Old Town Winchester](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 Old Town Winchester 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) #### George Washington's Office You can learn about the history of Winchester when you stop by George Washington's Office. While in this walkable area, you can savor the top-notch restaurants. [](https://expedia.ca/George-Washingtons-Office-Old-Town-Winchester.d6164042.Vacation-Attraction) #### Old Court House Civil War Museum You can study the exhibits at Old Court House Civil War Museum, a museum with a story of its own, during your trip to Winchester. While in this walkable area, you can savor the top-notch restaurants. [](https://expedia.ca/Old-Court-House-Civil-War-Museum-Old-Town-Winchester.d553248621532661844.Vacation-Attraction) * * * ## Old Town Winchester 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 Fully refundableReserve now, pay when you stay CA $178 CA $201 total Oct 26 - Oct 27 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! (1,010 reviews) "I’d return for sure. Our room was wonderful." Reviewed on Oct 10, 2025 [](https://expedia.ca/Hotel-Search?startDate=26%2F10%2F2025&endDate=27%2F10%2F2025&selected=1364026&PinnedHotelID=1364026&HadPinnedHotel=true®ionId=6164092) ![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 $144 CA $157 total Nov 2 - Nov 3 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! (2,184 reviews) "Was just one night with group of friends. Location was great, easy check in and out, good breakfast and comfy beds. Would highly recommend." Reviewed on Oct 12, 2025 [](https://expedia.ca/Hotel-Search?startDate=02%2F11%2F2025&endDate=03%2F11%2F2025&selected=2678524&PinnedHotelID=2678524&HadPinnedHotel=true®ionId=6164092) ![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 Fully refundableReserve now, pay when you stay CA $160 CA $181 total Oct 26 - Oct 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! (1,019 reviews) "Great stay! Would definitely would stay again!" Reviewed on Oct 10, 2025 [](https://expedia.ca/Hotel-Search?startDate=26%2F10%2F2025&endDate=27%2F10%2F2025&selected=19971&PinnedHotelID=19971&HadPinnedHotel=true®ionId=6164092) ![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 Oct 20 - Oct 21 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! (1,019 reviews) "The breakfast was good and a quiet place to stay" Reviewed on Oct 13, 2025 [](https://expedia.ca/Hotel-Search?startDate=20%2F10%2F2025&endDate=21%2F10%2F2025&selected=57958244&PinnedHotelID=57958244&HadPinnedHotel=true®ionId=6164092) ![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 $114 CA $124 total Nov 16 - Nov 17 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! (1,337 reviews) "Clean place good price" Reviewed on Oct 6, 2025 [](https://expedia.ca/Hotel-Search?startDate=16%2F11%2F2025&endDate=17%2F11%2F2025&selected=70921061&PinnedHotelID=70921061&HadPinnedHotel=true®ionId=6164092) ![Country Inn & Suites by Radisson, Winchester, VA](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/d0690cde_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Country Inn & Suites by Radisson, Winchester, VA 141 Kernstown Commons Blvd, Winchester, VA CA $128 CA $139 total Nov 9 - Nov 10 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 ... 8.6/10 Excellent! (1,017 reviews) "Nice hotel! Breakfast needs work" Reviewed on Oct 14, 2025 [](https://expedia.ca/Hotel-Search?startDate=09%2F11%2F2025&endDate=10%2F11%2F2025&selected=1652833&PinnedHotelID=1652833&HadPinnedHotel=true®ionId=6164092) [See all 367 properties in Old Town Winchester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=19%2F10%2F2025&endDate=20%2F10%2F2025®ionId=6164092) 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 Old Town Winchester hotel availability [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2025-10-18&endDate=2025-10-19) [Tonight](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2025-10-18&endDate=2025-10-19) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2025-10-18&endDate=2025-10-19) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2025-10-18&endDate=2025-10-19)[Oct 18 - Oct 19](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2025-10-18&endDate=2025-10-19) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2025-10-19&endDate=2025-10-20) [Tomorrow night](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2025-10-19&endDate=2025-10-20) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2025-10-19&endDate=2025-10-20) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2025-10-19&endDate=2025-10-20)[Oct 19 - Oct 20](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2025-10-19&endDate=2025-10-20) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=24%2F10%2F2025&endDate=26%2F10%2F2025) [Next weekend](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=24%2F10%2F2025&endDate=26%2F10%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=24%2F10%2F2025&endDate=26%2F10%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=24%2F10%2F2025&endDate=26%2F10%2F2025)[Oct 24 - Oct 26](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=24%2F10%2F2025&endDate=26%2F10%2F2025) * * * ### Other neighbourhoods around Old Town Winchester ![Default Image](https://mediaim.expedia.com/destination/1/720fb116634761161ecda43d4ca150e7.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Winchester Historic District While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Winchester Little Theater. [](https://expedia.ca/Winchester-Winchester-Historic-District.dx918789051029594112) * * * * * * - [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) # Old Town Winchester ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. 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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)