Title: Winchester Travel Guide: Best of Winchester, Virginia Travel 2026 | Expedia.co.uk [Hotels in Winchester](https://expedia.co.uk/Winchester-Hotels.d6056879.Travel-Guide-Hotels)[Holiday Rentals in Winchester](https://expedia.co.uk/Winchester-Holiday-Rentals.d6056879.Travel-Guide-HolidayRentals)[Flights to Winchester](https://expedia.co.uk/Cheap-Flights-To-Winchester.d6056879.Travel-Guide-Flights)[Winchester Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Winchester.d6056879.Car-Hire-Guide)[Winchester Holidays](https://expedia.co.uk/Winchester.d6056879.Holidays-City-Breaks) # Winchester Travel Guide ## Tourist Guide ![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 Winchester Where to stay Things to do ### Where to stay in Winchester ![Default Image](https://mediaim.expedia.com/destination/1/720fb116634761161ecda43d4ca150e7.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Old Town Winchester Old Town Winchester is popular for its abundant dining options, and if you're looking for more to see and do, you might think about a trip to Bright Box Theater or Shenandoah Valley Discovery Museum. [](https://expedia.co.uk/Winchester-Old-Town-Winchester.dx6164092) ![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) - Top hotels in Winchester - Top Holiday Rentals in Winchester ![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 £61 31 Dec - 1 Jan 2026 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! (1,379 reviews) Clean nice room with a hot breakfast, a lot nicer then other places in Winchester especially for the price. Highly recommend Reviewed on 13 Dec 2025 [](https://expedia.co.uk/Hotel-Search?startDate=31%2F12%2F2025&endDate=01%2F01%2F2026&selected=70921061&PinnedHotelID=70921061&HadPinnedHotel=true®ionId=6056879) ![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 £83 12 Jan - 13 Jan 2026 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! (2,221 reviews) Comfortable and clean room. Reviewed on 9 Dec 2025 [](https://expedia.co.uk/Hotel-Search?startDate=12%2F01%2F2026&endDate=13%2F01%2F2026&selected=2678524&PinnedHotelID=2678524&HadPinnedHotel=true®ionId=6056879) ![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 £80 12 Jan - 13 Jan 2026 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! (1,072 reviews) Great accomodations!! Reviewed on 6 Dec 2025 [](https://expedia.co.uk/Hotel-Search?startDate=12%2F01%2F2026&endDate=13%2F01%2F2026&selected=57958244&PinnedHotelID=57958244&HadPinnedHotel=true®ionId=6056879) [See all 2,036 properties in Winchester](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=16%2F12%2F2025&endDate=17%2F12%2F2025®ionId=6056879) 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. ![Dreamtime - Modern A-frame Cabin w/ Hot tub](https://images.trvl-media.com/lodging/73000000/72940000/72936100/72936072/9fcb6e62_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Dreamtime - Modern A-frame Cabin w/ Hot tub Berkeley Springs WV Stay at this cabin in Berkeley Springs. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Frog Valley Artisans, LTD and Colonial Springs Spa ... 9.8/10 Exceptional! (50 reviews) Everything about this place is top notch! We enjoyed Dreamtime cabin so much we probably spent more time in the cabin than out exploring. The home is well stocked with everything you could need from shampoo to kitchen supplies. We brought food to make all our meals in and had everything we needed. ... Reviewed on 24 Nov 2025 [](https://expedia.co.uk/Berkeley-Springs-Hotels-Dreamtime-Modern-A-Frame-Cabin-W-Hot-Tub.h72936072.Hotel-Information) !["Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.](https://images.trvl-media.com/lodging/23000000/22260000/22255700/22255620/f116a78a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### "Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA. Rileyville VA Stay at this cabin in Rileyville. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Chalybeate Spring and Fort Valley Public Library are ... 10/10 Exceptional! (324 reviews) Appreciated the great communication the host provided. We REALLY appreciated just how clean the cabin was. It was such a nice cabin to stay in for a quick 2-night get-away. It was the perfect layout and size for a cozy place for just the two of us. Hot tub was wonderful (and so clean!!!). The firepit ... Reviewed on 19 Nov 2025 [](https://expedia.co.uk/Rileyville-Hotels-Solitude-Spectacular-1-BR-Cabin-W-Hot-Tub-Near-Luray.h22255620.Hotel-Information) !["Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub ](https://images.trvl-media.com/lodging/23000000/22250000/22243700/22243657/edab5469_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### "Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub Rileyville VA Stay at this cabin in Rileyville. Enjoy free Wi-Fi, a garden and laundry facilities. Our guests praise the property condition in their reviews. Popular attractions ... 9.8/10 Exceptional! (331 reviews) My husband and I stayed at The Walden from November 21st to November 23rd, and it was an unforgettable experience. The home was spotless, beautifully maintained, and thoughtfully designed inside and out. The views from the property are absolutely stunning, adding to the peaceful and romantic atmosphere.We ... Reviewed on 23 Nov 2025 [](https://expedia.co.uk/Rileyville-Hotels-Walden-Spectacular-Riverfront-Cabin-On-54-Acres-Whot-Tub-Near-Luray.h22243657.Hotel-Information) [See all properties in Winchester](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=6056879&sort=VACATION_RENTAL) 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 Winchester hotel availability [Tonight ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6056879&startDate=2025-12-15&endDate=2025-12-16)[15 Dec - 16 Dec](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6056879&startDate=2025-12-15&endDate=2025-12-16) [Tomorrow night ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6056879&startDate=2025-12-16&endDate=2025-12-17)[16 Dec - 17 Dec](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6056879&startDate=2025-12-16&endDate=2025-12-17) [This weekend ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6056879&startDate=19%2F12%2F2025&endDate=21%2F12%2F2025)[19 Dec - 21 Dec](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6056879&startDate=19%2F12%2F2025&endDate=21%2F12%2F2025) [Next weekend ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6056879&startDate=26%2F12%2F2025&endDate=28%2F12%2F2025)[26 Dec - 28 Dec](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6056879&startDate=26%2F12%2F2025&endDate=28%2F12%2F2025) ### Popular places to visit ![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) ![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) #### Winchester Medical Center If Winchester Medical Center is what brings you to town, hopefully you'll have a chance to explore more of Winchester. [](https://expedia.co.uk/Winchester-Medical-Center-Winchester.d6164057.Attraction) #### Shenandoah University Enjoy the student vibe when you visit Shenandoah University during your trip to Winchester. While in this walkable area, you can savour the top-notch restaurants. [](https://expedia.co.uk/Shenandoah-University-Winchester.d6127311.Attraction) #### Apple Blossom Mall You can search for that perfect souvenir at Apple Blossom Mall during your stay in Winchester. While in this walkable area, you can savour the top-notch restaurants. [](https://expedia.co.uk/Apple-Blossom-Mall-Winchester.d6164018.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) ## Cities near Winchester ![Photo by Fernando Begay](https://mediaim.expedia.com/destination/2/54448e62c2e4970f24a2d5e76efbcc35.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Front Royal ![Berkeley Springs State Park which includes a park](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/135000/135329-Martinsburg-And-Vicinity.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Berkeley Springs ### Other places like Winchester - Cities near Winchester - Places of interest [Front Royal](https://expedia.co.uk/Front-Royal.dx7312)[Berkeley Springs](https://expedia.co.uk/Berkeley-Springs.dx55584) - [Winchester Medical Center ](https://expedia.co.uk/Winchester-Medical-Center-Winchester.d6164057.Attraction) - [Apple Blossom Mall ](https://expedia.co.uk/Apple-Blossom-Mall-Winchester.d6164018.Attraction) - [Shenandoah Valley Discovery Museum ](https://expedia.co.uk/Shenandoah-Valley-Discovery-Museum-Old-Town-Winchester.d553248621587527659.Attraction) - [Bright Box Theater ](https://expedia.co.uk/Bright-Box-Theater-Old-Town-Winchester.d553248621561864843.Attraction) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. 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