Title: Visit Old Town Winchester: 2026 Old Town Winchester, Winchester Travel Guide | Expedia.com [Hotels in Old Town Winchester](https://expedia.com/Old-Town-Winchester-Winchester-Hotels.0-n6164092-0.Travel-Guide-Filter-Hotels)[Flights to Winchester](https://expedia.com/Cheap-Flights-To-Winchester.d6056879.Travel-Guide-Flights)[Things to do in Winchester](https://expedia.com/Things-To-Do-In-Winchester.d6056879.Travel-Guide-Activities)[Car Rentals in Old Town Winchester](https://expedia.com/Car-Rentals-In-Old-Town-Winchester.d6164092.Car-Rental-Guide)[Old Town Winchester Vacations](https://expedia.com/Old-Town-Winchester.d6164092.Destination-Travel-Guides) # Old Town Winchester, VA ## Winchester ![The Courthouse in Winchester, Virginia.](https://images.trvl-media.com/place/6164092/74e89cff-4502-4b70-84ac-0bb3e6917b82.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![The Courthouse in Winchester, Virginia.](https://images.trvl-media.com/place/6164092/74e89cff-4502-4b70-84ac-0bb3e6917b82.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Handley Library ](https://images.trvl-media.com/place/6056879/dd3561a1-54d7-46cf-9e70-15a3b654b5eb.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![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=1040&h=580&q=mediumHigh) ![Holiday shopping in Winchester. ](https://images.trvl-media.com/place/6056879/62e1dbbb-36d3-4e34-8585-7fca068fd147.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ## Visit Old Town Winchester Things to do Hotels Where to stay [Winchester Travel Guide](https://expedia.com/Winchester.dx6056879) --- ### Popular places to visit ![Gardens at Glen Burnie House.](https://images.trvl-media.com/place/6056879/a8b6bc61-16a0-4bd7-8e9c-ba5025791cbb.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Museum of the Shenandoah Valley 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.com/Museum-Of-The-Shenandoah-Valley-Winchester.d6127313.Vacation-Attraction) ![Jim Barnett park](https://images.trvl-media.com/place/6056879/c975fc72-ad57-4298-afc1-a46af23cbed9.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Jim Barnett Park Explore the great outdoors at Jim Barnett Park, a lovely green space in Winchester. Check out the top-notch restaurants or charming coffeehouses in this walkable area. [](https://expedia.com/Jim-Barnett-Park-Winchester.d6164028.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.com/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.com/Bright-Box-Theater-Old-Town-Winchester.d553248621561864843.Vacation-Attraction) #### Handley Regional Library 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.com/Handley-Regional-Library-Old-Town-Winchester.d6164024.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.com/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 $127 nightly $143 total Feb 12 - Feb 13 Total with taxes and 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) Clean nice room Great location for restaurants Reviewed on Jan 28, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F12%2F2026&endDate=2%2F13%2F2026&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 $92 nightly $100 total Feb 15 - Feb 16 Total with taxes and 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! (2,258 reviews) Clean, bright, and up-to-date hotel. Friendly staff, warm pool, nice little exercise room. Standard hotel breakfast fare, but it was good, and staff was very kind about the bit of mess our toddlers made while eating (we offered to tidy up, and they said it was no problem!). Great experience. Reviewed on Jan 31, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F15%2F2026&endDate=2%2F16%2F2026&selected=2678524&PinnedHotelID=2678524&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 $80 nightly $87 total Feb 15 - Feb 16 Total with taxes and 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! (1,439 reviews) Room was very clean and spacious, staff was wonderful! Reviewed on Jan 31, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F15%2F2026&endDate=2%2F16%2F2026&selected=70921061&PinnedHotelID=70921061&HadPinnedHotel=true®ionId=6164092) ![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 $79 nightly $86 total Feb 15 - Feb 16 Total with taxes and 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! (1,001 reviews) The staff (phenomenal), the cleanliness, the attention to detail! The lady overseeing breakfast was a machine. Everything tidied up and perfect. The front desk staff were amazing!! Best staff we've ever seen and we travel a LOT!! 100% recommend staying here. It was less than a mile from the concert ... Reviewed on Jan 18, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F15%2F2026&endDate=2%2F16%2F2026&selected=172810&PinnedHotelID=172810&HadPinnedHotel=true®ionId=6164092) ![TownePlace Suites by Marriott Front Royal](https://images.trvl-media.com/lodging/37000000/36350000/36342700/36342604/0776aa15_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### TownePlace Suites by Marriott Front Royal 5 Caroline Drive Front Royal VA $116 nightly $128 total Feb 15 - Feb 16 Total with taxes and fees Book a stay at this business-friendly hotel in Front Royal. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ... 9.4/10 Exceptional! (561 reviews) Clean room, friendly and helpful staff, good breakfast, I would stay again. Reviewed on Jan 16, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F15%2F2026&endDate=2%2F16%2F2026&selected=36342604&PinnedHotelID=36342604&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 $102 nightly $115 total Feb 15 - Feb 16 Total with taxes and 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! (1,003 reviews) Pet friendly and they provided a goodie bag for my dog - very welcoming. Reviewed on Jan 13, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F15%2F2026&endDate=2%2F16%2F2026&selected=19971&PinnedHotelID=19971&HadPinnedHotel=true®ionId=6164092) [See all 369 properties in Old Town Winchester](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=2%2F6%2F2026&endDate=2%2F7%2F2026®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 [Tonight ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2026-02-05&endDate=2026-02-06)[Feb 5 - Feb 6](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2026-02-05&endDate=2026-02-06) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2026-02-06&endDate=2026-02-07)[Feb 6 - Feb 7](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2026-02-06&endDate=2026-02-07) [This weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2%2F6%2F2026&endDate=2%2F8%2F2026)[Feb 6 - Feb 8](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2%2F6%2F2026&endDate=2%2F8%2F2026) [Next weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2%2F13%2F2026&endDate=2%2F15%2F2026)[Feb 13 - Feb 15](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2%2F13%2F2026&endDate=2%2F15%2F2026) --- ### Other neighborhoods around Old Town Winchester ![Buildings and streets in the historic part of the ancient city of Winchester in Virginia.](https://images.trvl-media.com/place/918789051029594112/06c2fe17-e2c5-4e1c-941c-f181c2f40c91.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 Shenandoah Valley Discovery Museum. [](https://expedia.com/Winchester-Winchester-Historic-District.dx918789051029594112) [See our Where To Stay guide](https://expedia.com/Winchester.dx6056879.Where-To-Stay?rfrr=TG.LP.Dest.Neigh.Neighborhoods) --- --- - [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, VA ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - [Winchester Hotels ](https://www.expedia.com/Winchester-Hotels.d6056879.Travel-Guide-Hotels) - [Cheap Hotels in Winchester ](https://www.expedia.com/Winchester-Hotels-Cheap-Hotels.0-0-d6056879-tCheapHotels.Travel-Guide-Filter-Hotels) - [Pet-friendly Hotels in Winchester ](https://www.expedia.com/Winchester-Hotels-Pet-Friendly-Hotel.0-0-d6056879-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Motels in Winchester ](https://www.expedia.com/Winchester-Motels.d6056879-aaMotels.Travel-Guide-Accommodation) - 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