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) ![Old Town Winchester](https://images.trvl-media.com/place/6056879/dd3561a1-54d7-46cf-9e70-15a3b654b5eb.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Old Town Winchester](https://images.trvl-media.com/place/6056879/3acc501a-a330-4063-b538-b2368ef6a4c5.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Old Town Winchester](https://images.trvl-media.com/place/6056879/62e1dbbb-36d3-4e34-8585-7fca068fd147.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Old Town Winchester](https://images.trvl-media.com/place/6056879/b213b0d3-ce12-43d5-987b-6b4533cc11b3.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 ![Museum of the Shenandoah Valley](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 5/5(1 review) You can spend time browsing the exhibits at Museum of the Shenandoah Valley during your trip to Winchester. Visit the top-notch restaurants or cosy cafes 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) #### 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) #### 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) --- ## Top hotels in Old Town Winchester ![The George Washington Hotel, A Wyndham Grand Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364026/5707228d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The George Washington Hotel, A Wyndham Grand Hotel 103 E Piccadilly St Winchester VA £104 16 Apr - 17 Apr 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 ... 9.4/10 Exceptional! (1,002 reviews) This is a great renaissance hotel. The renovation of the interior is magnificent. The staff is very professional, competent and accommodating. Notables are the lobby including the bar and the pool spa. Best hotel shower head ever! The dining options in walking distance are fantastic. Definite return ... Reviewed on 31 Mar 2026 [](https://expedia.co.uk/Hotel-Search?startDate=16%2F04%2F2026&endDate=17%2F04%2F2026&selected=1364026&PinnedHotelID=1364026&HadPinnedHotel=true®ionId=6164092) ![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 £74 12 Apr - 13 Apr includes taxes & fees Stay at this business-friendly hotel in Winchester. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the breakfast and the helpful ... 9/10 Wonderful! (1,000 reviews) Breakfast was excellent and all the staff were very friendly. Reviewed on 30 Mar 2026 [](https://expedia.co.uk/Hotel-Search?startDate=12%2F04%2F2026&endDate=13%2F04%2F2026&selected=1889084&PinnedHotelID=1889084&HadPinnedHotel=true®ionId=6164092) ![La Quinta Inn & Suites by Wyndham Winchester](https://images.trvl-media.com/lodging/3000000/2680000/2678600/2678524/9e66afda_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### La Quinta Inn & Suites by Wyndham Winchester 1055 Millwood Pike, Route 50 East Winchester VA £90 5 Apr - 6 Apr 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! (2,268 reviews) The breakfast was subpar. Food was sparse Waffle maker didn't consistently work. Reviewed on 1 Apr 2026 [](https://expedia.co.uk/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=2678524&PinnedHotelID=2678524&HadPinnedHotel=true®ionId=6164092) ![Sleep Inn & Suites Winchester near University](https://images.trvl-media.com/lodging/1000000/900000/892900/892882/554af346_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sleep Inn & Suites Winchester near University 140 Costello Dr Winchester VA £69 16 Apr - 17 Apr 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 ... 7.8/10 Good! (1,001 reviews) I only stayed for about an hour. The room was freezing cold as it was dead of winter and freezing out. There was no heat turned on in the room when I got there so it was quite a while before the room actually reached a tolerable temperature Reviewed on 26 Mar 2026 [](https://expedia.co.uk/Hotel-Search?startDate=16%2F04%2F2026&endDate=17%2F04%2F2026&selected=892882&PinnedHotelID=892882&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 £74 29 Apr - 30 Apr 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 ... 9.2/10 Wonderful! (1,460 reviews) Being greeted by an alert and cheerful front desk person when checking in at 1 am set the tone for feeling comfortable about how the rest of the stay was going to go. i'll definitely try other Microtel Inn & Suites by Wyndham on my next trip. Reviewed on 29 Mar 2026 [](https://expedia.co.uk/Hotel-Search?startDate=29%2F04%2F2026&endDate=30%2F04%2F2026&selected=70921061&PinnedHotelID=70921061&HadPinnedHotel=true®ionId=6164092) ![Hampton Inn Winchester-University/Mall Area](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/c10d527c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn Winchester-University/Mall Area 640 East Jubal Early Drive Winchester VA £85 16 Apr - 17 Apr 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! (1,001 reviews) Nice lobby, nice room, ample parking, good breakfast selection, good area around the hotel Reviewed on 15 Mar 2026 [](https://expedia.co.uk/Hotel-Search?startDate=16%2F04%2F2026&endDate=17%2F04%2F2026&selected=19971&PinnedHotelID=19971&HadPinnedHotel=true®ionId=6164092) [See all 378 properties in Old Town Winchester](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=03%2F04%2F2026&endDate=04%2F04%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=2026-04-02&endDate=2026-04-03)[2 Apr - 3 Apr](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2026-04-02&endDate=2026-04-03) [Tomorrow night ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2026-04-03&endDate=2026-04-04)[3 Apr - 4 Apr](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2026-04-03&endDate=2026-04-04) [This weekend ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=03%2F04%2F2026&endDate=05%2F04%2F2026)[3 Apr - 5 Apr](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=03%2F04%2F2026&endDate=05%2F04%2F2026) [Next weekend ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=10%2F04%2F2026&endDate=12%2F04%2F2026)[10 Apr - 12 Apr](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=10%2F04%2F2026&endDate=12%2F04%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. 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