Title: Old Town Winchester Travel Guide: Best of Old Town Winchester, Winchester Travel 2025 | 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 cosy cafes or top-notch restaurants 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 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) #### 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) #### 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 £109 23 Nov - 24 Nov includes taxes & fees Stay at this 3.5-star spa hotel in Winchester. Enjoy free Wi-Fi, a full-service spa and 2 restaurants. Our guests praise the bar and the helpful staff in their ... 9.2/10 Wonderful! (1,001 reviews) Yes great hotel!! Reviewed on 12 Nov 2025 [](https://expedia.co.uk/Hotel-Search?startDate=23%2F11%2F2025&endDate=24%2F11%2F2025&selected=1364026&PinnedHotelID=1364026&HadPinnedHotel=true®ionId=6164092) ![Travelodge by Wyndham Winchester](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/1e2a7464_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Travelodge by Wyndham Winchester 160 Front Royal Pike Winchester VA Fully refundableReserve now, pay when you stay £58 14 Dec - 15 Dec 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 breakfast and the helpful staff in their reviews. ... 8.4/10 Very Good! (1,086 reviews) Clean room, friendly staff Reviewed on 10 Nov 2025 [](https://expedia.co.uk/Hotel-Search?startDate=14%2F12%2F2025&endDate=15%2F12%2F2025&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 £86 10 Dec - 11 Dec includes taxes & fees Stay at this 3-star business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful ... 9.2/10 Wonderful! (2,209 reviews) Nice place Reviewed on 11 Nov 2025 [](https://expedia.co.uk/Hotel-Search?startDate=10%2F12%2F2025&endDate=11%2F12%2F2025&selected=2678524&PinnedHotelID=2678524&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 £84 21 Nov - 22 Nov 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! (1,048 reviews) Nice room clean staff very nice Reviewed on 11 Nov 2025 [](https://expedia.co.uk/Hotel-Search?startDate=21%2F11%2F2025&endDate=22%2F11%2F2025&selected=57958244&PinnedHotelID=57958244&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 Fully refundableReserve now, pay when you stay £61 14 Dec - 15 Dec 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! (1,353 reviews) Quick, efficient and friendly. Just like I like it Reviewed on 14 Nov 2025 [](https://expedia.co.uk/Hotel-Search?startDate=14%2F12%2F2025&endDate=15%2F12%2F2025&selected=70921061&PinnedHotelID=70921061&HadPinnedHotel=true®ionId=6164092) ![Country Inn & Suites by Radisson, Winchester, VA](https://images.trvl-media.com/lodging/2000000/1660000/1652900/1652833/d0690cde_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Country Inn & Suites by Radisson, Winchester, VA 141 Kernstown Commons Blvd Winchester VA £80 24 Nov - 25 Nov includes taxes & fees Stay at this 3-star business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful ... 8.6/10 Excellent! (1,001 reviews) Comfortable beds, large bathrooms, quiet and good breakfast Reviewed on 11 Nov 2025 [](https://expedia.co.uk/Hotel-Search?startDate=24%2F11%2F2025&endDate=25%2F11%2F2025&selected=1652833&PinnedHotelID=1652833&HadPinnedHotel=true®ionId=6164092) [See all 371 properties in Old Town Winchester](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=18%2F11%2F2025&endDate=19%2F11%2F2025®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 [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2025-11-17&endDate=2025-11-18) [Tonight](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2025-11-17&endDate=2025-11-18) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2025-11-17&endDate=2025-11-18) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2025-11-17&endDate=2025-11-18)[17 Nov - 18 Nov](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2025-11-17&endDate=2025-11-18) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2025-11-18&endDate=2025-11-19) [Tomorrow night](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2025-11-18&endDate=2025-11-19) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2025-11-18&endDate=2025-11-19) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2025-11-18&endDate=2025-11-19)[18 Nov - 19 Nov](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2025-11-18&endDate=2025-11-19) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=21%2F11%2F2025&endDate=23%2F11%2F2025) [This weekend](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=21%2F11%2F2025&endDate=23%2F11%2F2025) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=21%2F11%2F2025&endDate=23%2F11%2F2025) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=21%2F11%2F2025&endDate=23%2F11%2F2025)[21 Nov - 23 Nov](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=21%2F11%2F2025&endDate=23%2F11%2F2025) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=28%2F11%2F2025&endDate=30%2F11%2F2025) [Next weekend](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=28%2F11%2F2025&endDate=30%2F11%2F2025) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=28%2F11%2F2025&endDate=30%2F11%2F2025) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=28%2F11%2F2025&endDate=30%2F11%2F2025)[28 Nov - 30 Nov](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=28%2F11%2F2025&endDate=30%2F11%2F2025) * * * ### 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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[Flights from Los Angeles (LAX) to Winchester (WGO)](https://www.expedia.co.uk/lp/flights/lax/wgo/los-angeles-to-winchester) - [Flights from London (LON) to Winchester (WGO)](https://www.expedia.co.uk/lp/flights/lon/wgo/london-to-winchester) - [Flights from Miami (MIA) to Winchester (WGO)](https://www.expedia.co.uk/lp/flights/mia/wgo/miami-to-winchester) - [Flights from Chicago (ORD) to Winchester (WGO)](https://www.expedia.co.uk/lp/flights/ord/wgo/chicago-to-winchester) - [Visit Aldie](https://www.expedia.co.uk/Aldie.dx553248622877094266) - [Apple Blossom Mall](https://www.expedia.co.uk/Apple-Blossom-Mall-Winchester.d6164018.Attraction) - [Visit Ashburn](https://www.expedia.co.uk/Ashburn.dx6035055) - [Barns of Rose Hill](https://www.expedia.co.uk/Barns-Of-Rose-Hill-Berryville.d553248621561864687.Attraction) - [Berryville Holidays](https://www.expedia.co.uk/Berryville.d184082.Holidays-City-Breaks) - [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) - [Visit Maurertown](https://www.expedia.co.uk/Maurertown.dx6353680) - [Visit Northern Virginia](https://www.expedia.co.uk/Northern-Virginia.dx6057018) - [Visit Oakton](https://www.expedia.co.uk/Oakton.dx553248634999273492) - [Visit Paeonian Springs](https://www.expedia.co.uk/Paeonian-Springs.dx3000355237) - [Visit Purcellville](https://www.expedia.co.uk/Purcellville.dx6338641) - [Visit Reston](https://www.expedia.co.uk/Reston.dx10437) - [Visit Rileyville](https://www.expedia.co.uk/Rileyville.dx3000460641) - [Visit Rixeyville](https://www.expedia.co.uk/Rixeyville.dx3000355269) - [Visit Round Hill](https://www.expedia.co.uk/Round-Hill.dx3000460647) - [Shenandoah Valley Discovery Museum](https://www.expedia.co.uk/Shenandoah-Valley-Discovery-Museum-Old-Town-Winchester.d553248621587527659.Attraction) - [Visit Shenandoah Valley](https://www.expedia.co.uk/Shenandoah-Valley.dx6023341) - [Visit Skyland](https://www.expedia.co.uk/Skyland.dx3000008006) - [Visit Springfield](https://www.expedia.co.uk/Springfield.dx9814) - [Visit Stevensburg](https://www.expedia.co.uk/Stevensburg.dx3000355296) - [Visit Syria](https://www.expedia.co.uk/Syria.dx184113) - [Visit The Plains](https://www.expedia.co.uk/The-Plains.dx3000460694) - [Visit Viewtown](https://www.expedia.co.uk/Viewtown.dx3000355328) - [Visit Ashton Heights](https://www.expedia.co.uk/Washington-Ashton-Heights.dx553248635976476822) - [Visit Baileys Crossroads](https://www.expedia.co.uk/Washington-Baileys-Crossroads.dx9534) - [Winchester Medical Center](https://www.expedia.co.uk/Winchester-Medical-Center-Winchester.d6164057.Attraction) - [Visit Woodville](https://www.expedia.co.uk/Woodville.dx553248635592808785) - [Ace New Zealand Rental Cars in Riverton](https://www.expedia.co.uk/ACE-New-Zealand-Car-Rentals-In-Riverton.d553248635975849884-c1106.Car-Rental-Guide-Suppliers) - [Avis Rental Cars in Winchester](https://www.expedia.co.uk/Avis-Car-Rentals-In-Winchester.d6056879-c41.Car-Rental-Guide-Suppliers) - [Car hire Paris](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Paris.d6050691.Car-Hire-Guide) - [Car hire Winchester](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Winchester.d6056879.Car-Hire-Guide) - [Car hire in Dollar Rent A Car Bd De La Marine](https://www.expedia.co.uk/Dollar-Rent-A-Car-at-Bd-De-La-Marine-Hyeres-FRA.v12076.Car-Rental-Guide-Location) - [Enterprise Rental Cars in Winchester](https://www.expedia.co.uk/Enterprise-Car-Rentals-In-Winchester.d6056879-c15.Car-Rental-Guide-Suppliers) - [Minivan Car Hire in Winchester](https://www.expedia.co.uk/Minivan-Car-Rentals-In-Winchester.d6056879-tMinivan.Car-Rental-Guide-Class) - [Winchester Holiday Rentals](https://www.expedia.co.uk/Winchester-Holiday-Rentals.d6056879.Travel-Guide-HolidayRentals) ![](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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