Title: Old Town Winchester Travel Guide: Best of Old Town Winchester, Winchester Travel 2026 | Expedia.co.uk [Hotels in Old Town Winchester](https://expedia.co.uk/Old-Town-Winchester-Winchester-Hotels.0-n6164092-0.Travel-Guide-Filter-Hotels)[Flights to Winchester](https://expedia.co.uk/Cheap-Flights-To-Winchester.d6056879.Travel-Guide-Flights)[Old Town Winchester Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Old-Town-Winchester.d6164092.Car-Hire-Guide)[Old Town Winchester Holidays](https://expedia.co.uk/Old-Town-Winchester.d6164092.Holidays-City-Breaks) # Old Town Winchester Travel Guide ## 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.co.uk/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 browsing the exhibits at Museum of the Shenandoah Valley during your trip to Winchester. Visit the cosy cafes or top-notch restaurants in this walkable area. [](https://expedia.co.uk/Museum-Of-The-Shenandoah-Valley-Winchester.d6127313.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. Visit the cosy cafes or top-notch restaurants in this walkable area. [](https://expedia.co.uk/Jim-Barnett-Park-Winchester.d6164028.Attraction) #### Bright Box Theater Enjoy a performance at Bright Box Theater, a popular theatre in Winchester. While in this walkable area, you can savour the top-notch restaurants. [](https://expedia.co.uk/Bright-Box-Theater-Old-Town-Winchester.d553248621561864843.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 savour the top-notch restaurants. [](https://expedia.co.uk/Shenandoah-Valley-Discovery-Museum-Old-Town-Winchester.d553248621587527659.Attraction) #### Handley Regional Library After visiting Handley Regional Library, make a plan to see the other sights and activities in Winchester. Visit the top-notch restaurants or cosy cafes in this walkable area. [](https://expedia.co.uk/Handley-Regional-Library-Old-Town-Winchester.d6164024.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 savour the top-notch restaurants. [](https://expedia.co.uk/Old-Court-House-Civil-War-Museum-Old-Town-Winchester.d553248621532661844.Attraction) --- ## Top hotels in Old Town Winchester ![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 £101 22 Feb - 23 Feb includes taxes & fees Stay at this spa hotel in Winchester. Enjoy free Wi-Fi, a full-service spa and 2 restaurants. Our guests praise the helpful staff and the clean rooms in their ... 9.2/10 Wonderful! (1,001 reviews) Clean nice room Great location for restaurants Reviewed on 28 Jan 2026 [](https://expedia.co.uk/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%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 £80 17 Feb - 18 Feb includes taxes & fees Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ... 9.2/10 Wonderful! (2,267 reviews) Staff was very courteous and friendly throught our entire stay! Everything was updated and very clean. Kids LOVED the pool and breakfast. Reviewed on 10 Feb 2026 [](https://expedia.co.uk/Hotel-Search?startDate=17%2F02%2F2026&endDate=18%2F02%2F2026&selected=2678524&PinnedHotelID=2678524&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 £67 22 Feb - 23 Feb includes taxes & fees Stay at this hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their reviews. ... 9.2/10 Wonderful! (1,000 reviews) Very clean Reviewed on 10 Feb 2026 [](https://expedia.co.uk/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=172810&PinnedHotelID=172810&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 £68 22 Feb - 23 Feb includes taxes & fees Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ... 9/10 Wonderful! (1,446 reviews) The only thing that disappointed me is that the breakfast potatoes and omelets were quite spice. I was unable to eat them. However, the room was excellent. Reviewed on 10 Feb 2026 [](https://expedia.co.uk/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=70921061&PinnedHotelID=70921061&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 £94 22 Feb - 23 Feb includes taxes & fees Stay at this business-friendly hotel in Front Royal. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ... 9.4/10 Exceptional! (562 reviews) Over all great! just wish the break was a little better. Reviewed on 8 Feb 2026 [](https://expedia.co.uk/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=36342604&PinnedHotelID=36342604&HadPinnedHotel=true®ionId=6164092) ![Hampton Inn Winchester N/Conference Center, VA](https://images.trvl-media.com/lodging/1000000/430000/424900/424883/cba33bb0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn Winchester N/Conference Center, VA 1204 Berryville Avenue Winchester VA £88 22 Feb - 23 Feb includes taxes & fees Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. ... 9.2/10 Wonderful! (861 reviews) The staff was wonderful! Reviewed on 30 Jan 2026 [](https://expedia.co.uk/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=424883&PinnedHotelID=424883&HadPinnedHotel=true®ionId=6164092) [See all 370 properties in Old Town Winchester](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=17%2F02%2F2026&endDate=18%2F02%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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-uk-fr-de.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Holiday Sale Members save up to 40% on hotels and holiday homes. Plan this year’s big trip and save. [Book now](https://expedia.co.uk/cheap-deals?rfrr=DX-NH_SPRING_PROMO_6164092) ## Check Old Town Winchester hotel availability [Tonight ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2026-02-16&endDate=2026-02-17)[16 Feb - 17 Feb](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2026-02-16&endDate=2026-02-17) [Tomorrow night ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2026-02-17&endDate=2026-02-18)[17 Feb - 18 Feb](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2026-02-17&endDate=2026-02-18) [This weekend ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=20%2F02%2F2026&endDate=22%2F02%2F2026)[20 Feb - 22 Feb](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=20%2F02%2F2026&endDate=22%2F02%2F2026) [Next weekend ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=27%2F02%2F2026&endDate=01%2F03%2F2026)[27 Feb - 1 Mar](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=27%2F02%2F2026&endDate=01%2F03%2F2026) --- ### Other neighbourhoods 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.co.uk/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 Travel Guide ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Holiday Homes - [4 Star Hotels in Winchester ](https://www.expedia.co.uk/4Star-Winchester-Hotels.s40-0-d6056879.Travel-Guide-Filter-Hotels) - [Berryville Hotels ](https://www.expedia.co.uk/Berryville-Hotels.d184082.Travel-Guide-Hotels) - [Hilton Hotels in Boyce ](https://www.expedia.co.uk/Boyce-Hotels-Hilton-Hotels.0-0-d184084--bHiltonHotels.Travel-Guide-Filter-Hotels) - [Boyce Hotels ](https://www.expedia.co.uk/Boyce-Hotels.d184084.Travel-Guide-Hotels) - [Hotels near Dinosaur Land ](https://www.expedia.co.uk/Dinosaur-Land-Hotels.0-l553248621532661835-0.Travel-Guide-Filter-Hotels) - 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