Old Town Winchester Travel Guide
Winchester
Visit Old Town Winchester
Popular places to visit
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 cosy cafes or top-notch restaurants in this walkable area.
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.
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.
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.
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.
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.
Top hotels in Old Town Winchester
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
The price is £104 per night from 7 Jun to 8 Jun
£104
7 Jun - 8 Jun
includes taxes & fees
Stay at this spa hotel in Winchester. Enjoy free Wi-Fi, a full-service spa and 2 restaurants. Our guests praise the helpful staff and the clean rooms in their ...
9.4/10 Exceptional! (1,005 reviews)
You can’t go wrong staying here. The staff were very friendly. The beds were very comfortable and the room was very clean. This hotel is centrally located so you can park your car and walk around the old town area. This was our second time staying here and it didn’t disappoint. We will definitely ...
Reviewed on 17 May 2026
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
The price is £65 per night from 31 May to 1 Jun
£65
31 May - 1 Jun
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking and a fitness centre. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,017 reviews)
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Reviewed on 17 May 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
The price is £58 per night from 24 May to 25 May
£58
24 May - 25 May
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 helpful staff and the clean rooms in their reviews. ...
8.6/10 Excellent! (1,073 reviews)
Comfortable for the 1 night I needed room for
Reviewed on 17 May 2026
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
The price is £76 per night from 25 May to 26 May
£76
25 May - 26 May
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 ...
9.2/10 Wonderful! (1,461 reviews)
The room and property were clean and comfortable. Staff were professional and friendly. Although a “micro” hotel, room and bathroom were efficient, yet plenty big enough. Bed was very comfortable.
Reviewed on 17 May 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
The price is £81 per night from 24 May to 25 May
£81
24 May - 25 May
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! (1,002 reviews)
You have to pay 8.00 for breakfast, but it was very good. Room was clean, safe location.
Reviewed on 16 May 2026
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
The price is £95 per night from 24 May to 25 May
£95
24 May - 25 May
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! (2,272 reviews)
Be Aware!! Parking was a bit hard( we were pulling an enclosed trailer) had to back out from around the building because it did not circle all the way around . Room was clean and comfortable bed was soft, breakfast was the usually continental hot breakfast nothing special but ok. Would stay ...
Reviewed on 15 May 2026
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.
Other neighbourhoods around Old Town Winchester
Winchester Historic District
While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Shenandoah Valley Discovery Museum.
Old Town Winchester Travel Guide
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- Visit Aldie
- Apple Blossom Mall
- Visit Ashburn
- Barns of Rose Hill
- Berryville Holidays
- Visit Bluemont
- Boyce Holidays
- Bright Box Theater
- Visit Chantilly
- Visit Criders
- Visit Culpeper
- Visit Dale City
- Dinosaur Land
- Visit Fairfax
- Visit Falls Church
- Visit Front Royal
- Visit Linden
- Mackintosh Fruit Farm
- Visit Maurertown
- Visit Northern Virginia
- Visit Oakton
- Visit Paeonian Springs
- Visit Purcellville
- Visit Reston
- Visit Rileyville
- Visit Rixeyville
- Visit Round Hill
- Shenandoah Valley Discovery Museum
- Visit Shenandoah Valley
- Visit Skyland
- Visit Springfield
- Visit Stevensburg
- Visit Syria
- Visit The Plains
- Visit Viewtown
- Visit Ashton Heights
- Visit Baileys Crossroads
- Winchester Medical Center
- Visit Woodville
