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://images.trvl-media.com/place/6056879/5a1e10ca-c30d-4d41-816e-f5af84673df6.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![MAY 9, 2023 - WINCHESTER, KENTUCKY - aerial view of historic small town of Winchester with Town Clocktower and historic storefronts and buildings](https://images.trvl-media.com/place/6056879/31f89911-167f-41d8-88d6-62f9fb8763d2.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) ![Gardens at Glen Burnie House.](https://images.trvl-media.com/place/6056879/a8b6bc61-16a0-4bd7-8e9c-ba5025791cbb.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) ## Visit Winchester Where to stay Things to do ### Where to stay in Winchester ![The Courthouse in Winchester, Virginia.](https://images.trvl-media.com/place/6164092/74e89cff-4502-4b70-84ac-0bb3e6917b82.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) ![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) - Top hotels in Winchester - Top Holiday Rentals in Winchester ![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 Fully refundableReserve now, pay when you stay £74 29 Mar - 30 Mar 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) Convenient location. The pool is clean and fitness facility is quite good. Breakfast is excellent and in good service. Reviewed on 23 Mar 2026 [](https://expedia.co.uk/Hotel-Search?startDate=29%2F03%2F2026&endDate=30%2F03%2F2026&selected=1889084&PinnedHotelID=1889084&HadPinnedHotel=true®ionId=6056879) ![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 £87 26 Mar - 27 Mar 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! (2,279 reviews) Room was clean, lobby and staff friendly. This is our second time staying so we always enjoy coming. Reviewed on 23 Mar 2026 [](https://expedia.co.uk/Hotel-Search?startDate=26%2F03%2F2026&endDate=27%2F03%2F2026&selected=2678524&PinnedHotelID=2678524&HadPinnedHotel=true®ionId=6056879) ![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 £65 22 Apr - 23 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! (1,002 reviews) The room was very clean. The staff are friendly. Nice place to stay. Reviewed on 23 Mar 2026 [](https://expedia.co.uk/Hotel-Search?startDate=22%2F04%2F2026&endDate=23%2F04%2F2026&selected=892882&PinnedHotelID=892882&HadPinnedHotel=true®ionId=6056879) [See all 2,040 properties in Winchester](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=26%2F03%2F2026&endDate=27%2F03%2F2026®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. ![Cozy Bear Cottage! Hot Tub! Warm toasty fireplace!](https://images.trvl-media.com/lodging/43000000/42620000/42617400/42617315/32780271_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Cozy Bear Cottage! Hot Tub! Warm toasty fireplace! Luray VA Stay at this cabin in Luray. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Luray Caverns and Dukes of Hazzard Museum are located ... [](https://expedia.co.uk/Luray-Hotels-A-Cozy-Bear-Cottage-Clean-And-Secluded.h42617315.Hotel-Information) ![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 ... 10/10 Exceptional! (57 reviews) The house was beautiful and well taken care of. We had everything we needed to just hold up cozy in the house. The hot tub was a great ammenity. Reviewed on 23 Jan 2026 [](https://expedia.co.uk/Berkeley-Springs-Hotels-Dreamtime-Modern-A-Frame-Cabin-W-Hot-Tub.h72936072.Hotel-Information) ![Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo](https://images.trvl-media.com/lodging/27000000/26970000/26968400/26968349/88605fc6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo Front Royal VA Stay at this cabin in Front Royal. Enjoy a garden, patios and an in-room coffee maker. Popular attractions Glen Manor Vineyards and Shenandoah River State Park ... 9.6/10 Exceptional! (343 reviews) The space was cozy and nice. The view of the river was absolutely breathtaking from the back porch! Quiet and relaxing. Reviewed on 23 Mar 2026 [](https://expedia.co.uk/Winchester-Hotels-Log-Cabin-With-A-Spectacular-View-Of-The-Shenandoah-River-And-The-Massanutten-Mo.h26968349.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=2026-03-25&endDate=2026-03-26)[25 Mar - 26 Mar](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6056879&startDate=2026-03-25&endDate=2026-03-26) [Tomorrow night ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6056879&startDate=2026-03-26&endDate=2026-03-27)[26 Mar - 27 Mar](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6056879&startDate=2026-03-26&endDate=2026-03-27) [This weekend ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6056879&startDate=27%2F03%2F2026&endDate=29%2F03%2F2026)[27 Mar - 29 Mar](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6056879&startDate=27%2F03%2F2026&endDate=29%2F03%2F2026) [Next weekend ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6056879&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=6056879&startDate=03%2F04%2F2026&endDate=05%2F04%2F2026) ### 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 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 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) #### ValleyHealth Winchester Medical Center If ValleyHealth Winchester Medical Center is what brings you to town, hopefully you'll have a chance to explore more of Winchester. [](https://expedia.co.uk/ValleyHealth-Winchester-Medical-Center-Winchester.d6164057.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 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 ![Trees - Bear Church Rock Trail, Shenandoah National Park, Virginia](https://images.trvl-media.com/place/7312/1e808d74-e702-47a6-a388-ce77751dfd04.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Front Royal ![Berkeley Springs State Park which includes a park](https://images.trvl-media.com/place/6093893/7080036c-422a-4869-817b-5185eda595fb.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) - [ValleyHealth Winchester Medical Center ](https://expedia.co.uk/ValleyHealth-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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