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 top-notch restaurants or cosy cafes 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.
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.
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.
Top hotels in Old Town Winchester
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
The price is ₹11,604 per night from 29 Jan to 30 Jan
₹11,604
₹13,147 total
29 Jan - 30 Jan
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 ...
9.2/10 Wonderful! (1,005 reviews)
Everything was great. John that checked me in was a huge help with my luggage. When I was leaving the next day there was an older man that works at the hotel that was telling me all about the history of the hotel, I loved that! The room was clean and comfortable. I loved the older furniture and art ...
Reviewed on 20 Jan 2026
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
The price is ₹7,483 per night from 26 Jan to 27 Jan
₹7,483
₹8,142 total
26 Jan - 27 Jan
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! (1,437 reviews)
Perfect for a single night, relatively clean, very friendly staff and decent breakfast.
Reviewed on 18 Jan 2026
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
The price is ₹8,411 per night from 27 Jan to 28 Jan
₹8,411
₹9,151 total
27 Jan - 28 Jan
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! (2,248 reviews)
Clean room. Friendly and helpful staff.
Reviewed on 21 Jan 2026
Comfort Inn & Suites Winchester
195 Kernstown Commons Blvd Winchester VA
The price is ₹8,968 per night from 8 Feb to 9 Feb
₹8,968
₹9,757 total
8 Feb - 9 Feb
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! (1,098 reviews)
All of the above
Reviewed on 21 Jan 2026
Quality Inn Winchester
1601 Martinsburg Pike Winchester VA
The price is ₹7,547 per night from 20 Feb to 21 Feb
₹7,547
₹8,211 total
20 Feb - 21 Feb
includes taxes & fees
Stay at this hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their reviews. ...
9.2/10 Wonderful! (1,005 reviews)
The staff (phenomenal), the cleanliness, the attention to detail! The lady overseeing breakfast was a machine. Everything tidied up and perfect. The front desk staff were amazing!! Best staff we've ever seen and we travel a LOT!! 100% recommend staying here. It was less than a mile from the concert ...
Reviewed on 18 Jan 2026
Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr Strasburg VA
The price is ₹7,093 per night from 19 Feb to 20 Feb
₹7,093
₹7,895 total
19 Feb - 20 Feb
includes taxes & fees
Stay at this business-friendly hotel in Strasburg. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in ...
8.2/10 Very Good! (1,000 reviews)
Great stay everyone friendly will stay again
Reviewed on 19 Jan 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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