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 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 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) #### 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) #### 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) * * * ## 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 £106 9 Oct - 10 Oct 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! (1,000 reviews) "The beauty of the property to begin with. Old world charm but modernized without detracting from the original character. The grand mailbox, each floor having a mailbox which directly connects with and is fed by gravity to the “grand” collection box on the ground floor! Beautiful! The basement pool ..." Reviewed on 24 Sept 2025 [](https://expedia.co.uk/Hotel-Search?startDate=09%2F10%2F2025&endDate=10%2F10%2F2025&selected=1364026&PinnedHotelID=1364026&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 £87 26 Oct - 27 Oct 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! (2,158 reviews) "Convenient off I-81, clean, quiet,nice warm breakfast, even great dark roast coffee. Will definitely make this a stop on our way south annually" Reviewed on 1 Oct 2025 [](https://expedia.co.uk/Hotel-Search?startDate=26%2F10%2F2025&endDate=27%2F10%2F2025&selected=2678524&PinnedHotelID=2678524&HadPinnedHotel=true®ionId=6164092) ![Hampton Inn Winchester-University/Mall Area](https://images.trvl-media.com/lodging/1000000/20000/20000/19971/17b0fc68_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn Winchester-University/Mall Area 640 East Jubal Early Drive, Winchester, VA £89 8 Oct - 9 Oct 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! (1,014 reviews) "We needed a break with a long family care situation. We took a break and stayed in Winchester and relaxed. Hampton Inn was just perfect. Breakfast was great! Thank you!" Reviewed on 28 Sept 2025 [](https://expedia.co.uk/Hotel-Search?startDate=08%2F10%2F2025&endDate=09%2F10%2F2025&selected=19971&PinnedHotelID=19971&HadPinnedHotel=true®ionId=6164092) ![Travelodge by Wyndham Winchester](https://images.trvl-media.com/lodging/1000000/10000/9600/9600/28616e5b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Travelodge by Wyndham Winchester 160 Front Royal Pike, Winchester, VA £56 3 Nov - 4 Nov 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! (1,100 reviews) "Good no frills hotel for an overnight stay. Easy off/on Interstate. Room was clean, bed comfotable, breakfast fine (make your own waffles!), staff very friendly. We had a nice quiet night & would stay again." Reviewed on 27 Sept 2025 [](https://expedia.co.uk/Hotel-Search?startDate=03%2F11%2F2025&endDate=04%2F11%2F2025&selected=9600&PinnedHotelID=9600&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 £63 31 Oct - 1 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 helpful staff and the clean rooms ... 9/10 Wonderful! (1,353 reviews) "Great place with very cute rooms!!" Reviewed on 29 Sept 2025 [](https://expedia.co.uk/Hotel-Search?startDate=31%2F10%2F2025&endDate=01%2F11%2F2025&selected=70921061&PinnedHotelID=70921061&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 £73 2 Nov - 3 Nov includes taxes & fees Stay at this 3-star business-friendly hotel in Winchester. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the breakfast and the ... 9/10 Wonderful! (1,001 reviews) "The room was spacious." Reviewed on 1 Oct 2025 [](https://expedia.co.uk/Hotel-Search?startDate=02%2F11%2F2025&endDate=03%2F11%2F2025&selected=1889084&PinnedHotelID=1889084&HadPinnedHotel=true®ionId=6164092) [See all 366 properties in Old Town Winchester](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=04%2F10%2F2025&endDate=05%2F10%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=2025-10-03&endDate=2025-10-04) [Tonight](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2025-10-03&endDate=2025-10-04) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2025-10-03&endDate=2025-10-04) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2025-10-03&endDate=2025-10-04)[3 Oct - 4 Oct](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2025-10-03&endDate=2025-10-04) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2025-10-04&endDate=2025-10-05) [Tomorrow night](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2025-10-04&endDate=2025-10-05) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2025-10-04&endDate=2025-10-05) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2025-10-04&endDate=2025-10-05)[4 Oct - 5 Oct](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=2025-10-04&endDate=2025-10-05) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=03%2F10%2F2025&endDate=05%2F10%2F2025) [This weekend](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=03%2F10%2F2025&endDate=05%2F10%2F2025) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=03%2F10%2F2025&endDate=05%2F10%2F2025) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=03%2F10%2F2025&endDate=05%2F10%2F2025)[3 Oct - 5 Oct](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6164092&startDate=03%2F10%2F2025&endDate=05%2F10%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 Winchester Little Theater. [](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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