Downtown Winchester, Virginia

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Fun things to do in Winchester, Virginia
  • Main Street of old Downtown Winchester speaks to once what was and what could be once again. As Winchester the community gathers, it leaves a pocket of opportunity for small business owners to come in and set up shop.Take a few minutes to explore what each downtown has to offer by viewing our directory below.
  • Downtown Winchester offers on-the-go dining when you visit your favorite food truck. Pick up some corn tortilla tacos with freshly made pico with a fresh squeeze of lemon to give your day a boost. Food trucks can offer a wide variety of niche ethnic blends.

  • Downtown Winchester makes shopping for wine and other spirits easy by bringing an incredible collection sourced from local, regional well-known producers from around the World. Hit the wine tasting events and stock up on your favorite choice to be shipped home for your convenience.

  • Downtown Winchester micro breweries have popped up in downtown corridors to quench the thirst of local or traveller whos is looking for a one-of-a-kind experience for suds brewed on site. If you are looking for a light beer or something randy and dark, you are sure to find a wide assortment of options to choose from.

  • Downtown Winchester brings meaning to leisure time while enjoying the local yarn shop and wandering through in amazement with the different fibers and vast array of colors. Signing up for a class is easy and fun and serves as a great getaway for a few hours to enjoy the company of fellow knitters.





A Matter Of Taste

175 Horizon Drive
Downtown Winchester



Apple Blossom Country Market

1184 Millwood Pike G
Downtown Winchester



Allen Properties

1042 Berryville Avenue
Downtown Winchester



Bedrock Group

168 North Loudoun St
Downtown Winchester



Downtown Winchester Hotels

Finding the best hotel in Downtown Winchester can make or break the experience of your entire trip. Take a few minutes to explore what each hotel has to offer by viewing our directory below. Here are some tips to consider:



Sleep Inn & Suites
140 Costello Dr
Downtown Winchester


TownePlace Suites by Marriott Winchester
170 Getty Ln
Downtown Winchester


Wingate by Wyndham - Winchester
150 Wingate Dr
Downtown Winchester


BEST WESTERN LEE JACKSON INN
711 MILLWOOD AVE
Downtown Winchester


Holiday Inn Winchester Se-Historic Gateway
333 Front Royal Pike
Downtown Winchester


The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St
Downtown Winchester


Econo Lodge North
1593 Martinsburg Pike
Downtown Winchester


Fairfield & Suites by Marriott Winchester
250 Front Royal Pike
Downtown Winchester


Travelodge - Winchester
160 Front Royal Pike
Downtown Winchester


Super 8 Winchester Va
1077 Millwood Pike
Downtown Winchester


Country Inn & Suites By Carlson, Winchester, VA
141 Kernstown Commons Blvd
Downtown Winchester


Comfort Inn Winchester
1601 Martinsburg Pike
Downtown Winchester


Hilton Garden Inn Winchester
120 Wingate Drive
Downtown Winchester


Courtyard by Marriott Winchester
300 Marriott Drive
Downtown Winchester


Hampton Inn - Winchester N/Convention Center
1204 Berryville Avenue
Downtown Winchester


Hampton Inn Winchester-University/Mall Area
1655 Apple Blossom Dr
Downtown Winchester


Holiday Inn Express Hotel & Suites Winchester
142 Foxridge Ln
Downtown Winchester


Aloft Winchester
1055 Millwood Pike (Rt. 50 East)
Downtown Winchester


Red Roof Inn Winchester, VA
991 Millwood Pike
Downtown Winchester


Candlewood Suites Winchester
1135 Millwood Pike
Downtown Winchester


Americas Best Value Inn
2649 Valley Ave
Downtown Winchester




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Copyright 2017, 2018 & 2019. "Shop Downtown" is an unregistered trademark owned by Daniel Wells
based on first use in commerce on February 14, 2013.

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