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 ![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.co.uk/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 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) ![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 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) #### Shenandoah Valley Discovery Museum 4/5(1 review) 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) #### 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) #### 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) #### George Washington's Office You can find out about the history of Winchester with a visit to George Washington's Office. While in this walkable area, you can savour the top-notch restaurants. [](https://expedia.co.uk/George-Washingtons-Office-Old-Town-Winchester.d6164042.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 £107 15 Jan - 16 Jan 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! (1,009 reviews) I love this hotel. I have stayed here once or twice a year over the past few years for the affordability, cleanliness, pool, hot tub, and location on my way up north. This past stay I noticed they are doing their best to keep up with increasing maintenance demands and decreasing profits. Reviewed on 29 Dec 2025 [](https://expedia.co.uk/Hotel-Search?startDate=15%2F01%2F2026&endDate=16%2F01%2F2026&selected=1364026&PinnedHotelID=1364026&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 £64 5 Jan - 6 Jan 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! (1,402 reviews) Great staff. Clean room. Excellent location Reviewed on 26 Dec 2025 [](https://expedia.co.uk/Hotel-Search?startDate=05%2F01%2F2026&endDate=06%2F01%2F2026&selected=70921061&PinnedHotelID=70921061&HadPinnedHotel=true®ionId=6164092) ![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 £55 18 Jan - 19 Jan includes taxes & fees Stay at this motel in Winchester. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in their reviews. ... 8.4/10 Very Good! (1,080 reviews) All of the above mentioned and a great, nutritious and varied breakfast. Also, both regular and decaf coffee were available in the breakfast area whenever I wanted it. Lastly, plentiful parking. Reviewed on 27 Dec 2025 [](https://expedia.co.uk/Hotel-Search?startDate=18%2F01%2F2026&endDate=19%2F01%2F2026&selected=9600&PinnedHotelID=9600&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 5 Jan - 6 Jan 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! (2,239 reviews) Everything was great Reviewed on 28 Dec 2025 [](https://expedia.co.uk/Hotel-Search?startDate=05%2F01%2F2026&endDate=06%2F01%2F2026&selected=2678524&PinnedHotelID=2678524&HadPinnedHotel=true®ionId=6164092) ![Days Inn by Wyndham Charles Town/Harpers Ferry](https://images.trvl-media.com/lodging/11000000/10630000/10620700/10620696/6feea908_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Days Inn by Wyndham Charles Town/Harpers Ferry 642 E Washington Street Charles Town WV £56 5 Jan - 6 Jan includes taxes & fees Stay at this business-friendly hotel in Charles Town. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ... 7.8/10 Good! (1,001 reviews) The room is clean. The staff is friendly. The breakfast was good. No-frills hotel, but clean and efficient. Reviewed on 13 Dec 2025 [](https://expedia.co.uk/Hotel-Search?startDate=05%2F01%2F2026&endDate=06%2F01%2F2026&selected=10620696&PinnedHotelID=10620696&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 £77 25 Jan - 26 Jan 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 ... 9.4/10 Exceptional! (1,090 reviews) The facilities were very clean. Location was great. Staff was super helpful and nice. My only issue: Curtains! Our room faced the parking lot in front of the hotel. The lot is very well lit, which is much appreciated, but the heavy curtains in our room could not be drawn together. The light one do, ... Reviewed on 29 Dec 2025 [](https://expedia.co.uk/Hotel-Search?startDate=25%2F01%2F2026&endDate=26%2F01%2F2026&selected=57958244&PinnedHotelID=57958244&HadPinnedHotel=true®ionId=6164092) [See all 362 properties in Old Town Winchester](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=02%2F01%2F2026&endDate=03%2F01%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.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2026-01-01&endDate=2026-01-02)[1 Jan - 2 Jan](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2026-01-01&endDate=2026-01-02) [Tomorrow night ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2026-01-02&endDate=2026-01-03)[2 Jan - 3 Jan](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2026-01-02&endDate=2026-01-03) [This weekend ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=02%2F01%2F2026&endDate=04%2F01%2F2026)[2 Jan - 4 Jan](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=02%2F01%2F2026&endDate=04%2F01%2F2026) [Next weekend ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=09%2F01%2F2026&endDate=11%2F01%2F2026)[9 Jan - 11 Jan](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=09%2F01%2F2026&endDate=11%2F01%2F2026) --- ### 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 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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[Visit Bluemont ](https://www.expedia.co.uk/Bluemont.dx6348602) - [Boyce Holidays ](https://www.expedia.co.uk/Boyce.d184084.Holidays-City-Breaks) - [Bright Box Theater ](https://www.expedia.co.uk/Bright-Box-Theater-Old-Town-Winchester.d553248621561864843.Attraction) - [Visit Chantilly ](https://www.expedia.co.uk/Chantilly.dx8638) - [Visit Criders ](https://www.expedia.co.uk/Criders.dx553248635592893970) - [Visit Culpeper ](https://www.expedia.co.uk/Culpeper.dx10640) - [Visit Dale City ](https://www.expedia.co.uk/Dale-City.dx3000459889) - [Dinosaur Land ](https://www.expedia.co.uk/Dinosaur-Land-White-Post.d553248621532661835.Attraction) - [Visit Fairfax ](https://www.expedia.co.uk/Fairfax.dx8062) - [Visit Falls Church ](https://www.expedia.co.uk/Falls-Church.dx8077) - [Visit Front Royal ](https://www.expedia.co.uk/Front-Royal.dx7312) - [Visit Linden ](https://www.expedia.co.uk/Linden.dx3000460101) - [Mackintosh Fruit Farm ](https://www.expedia.co.uk/Mackintosh-Fruit-Farm-Berryville.d553248621532661930.Attraction) - 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