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.
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 ₹12,336 per night from 19 May to 20 May
₹12,336
₹13,976 total
19 May - 20 May
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)
Staff was excellent- friendly, courteous. Helpful. Gym - small - but clean and most that you need. Pool - beautiful- on smaller side. Great bar vibe. Excellent location. This Wyndham so much better quality than the Wyndham we stayed at in Savannah, GA. Uno Pizzaria - connected to hotel - terrible ...
Reviewed on 2 May 2026
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
The price is ₹7,908 per night from 31 May to 1 Jun
₹7,908
₹8,960 total
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! (1,023 reviews)
Clean room, friendly front desk
Reviewed on 6 May 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
Fully refundableReserve now, pay when you stay
The price is ₹6,717 per night from 10 May to 11 May
₹6,717
₹7,309 total
10 May - 11 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! (1,057 reviews)
Clean and comfortable. Good for the price.
Reviewed on 6 May 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
The price is ₹8,799 per night from 24 May to 25 May
₹8,799
₹9,858 total
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! (1,010 reviews)
Perfect hotel. I love this hotel.
Reviewed on 5 May 2026
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
The price is ₹9,083 per night from 1 Jun to 2 Jun
₹9,083
₹9,882 total
1 Jun - 2 Jun
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! (1,452 reviews)
Quiet. Very nice front desk lady gave us extra blankets when we asked. Great breakfast!
Reviewed on 6 May 2026
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
The price is ₹10,967 per night from 12 May to 13 May
₹10,967
₹11,932 total
12 May - 13 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! (2,275 reviews)
Quiet clean room. Had dog with me. staff was very kind about his barking. They have a special floor for dogs.
Reviewed on 5 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.
Check Old Town Winchester hotel availability
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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