Old Town Winchester, VA
Winchester
Visit Old Town Winchester
Popular places to visit
Museum of the Shenandoah Valley
You can spend time exploring the galleries in Museum of the Shenandoah Valley during your trip to Winchester. Check out the top-notch restaurants or charming coffeehouses in this walkable area.
Jim Barnett Park
Explore the great outdoors at Jim Barnett Park, a lovely green space in Winchester. Check out the charming coffeehouses 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 savor the top-notch restaurants.
Bright Box Theater
Enjoy a show at Bright Box Theater, a storied theater in Winchester. While in this walkable area, you can savor 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 savor the top-notch restaurants.
Handley Regional Library
After visiting Handley Regional Library, make a plan to see the other sights and activities in Winchester. Check out the top-notch restaurants or charming coffeehouses in this walkable area.
Old Town Winchester Hotel Deals
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
$122 nightly
The price is $138 total per night from Apr 12 to Apr 13
$138 total
Apr 12 - Apr 13
Total with taxes and fees
Book a stay at this spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
9.4/10 Exceptional! (1,003 reviews)
This is a great renaissance hotel. The renovation of the interior is magnificent. The staff is very professional, competent and accommodating. Notables are the lobby including the bar and the pool spa. Best hotel shower head ever! The dining options in walking distance are fantastic. Definite return ...
Reviewed on Mar 31, 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
$91 nightly
The price is $99 total per night from Apr 12 to Apr 13
$99 total
Apr 12 - Apr 13
Total with taxes and fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
9/10 Wonderful! (1,001 reviews)
Best breakfast in town but must get breakfast coupons when selecting yhis hotel. Carpets old and need refreshing Needs a little tlc
Reviewed on Apr 4, 2026
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
$110 nightly
The price is $119 total per night from Apr 5 to Apr 6
$119 total
Apr 5 - Apr 6
Total with taxes and fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (2,271 reviews)
Parking was convenient. I didn’t get up in time for the breakfast.
Reviewed on Apr 4, 2026
Sleep Inn & Suites Winchester near University
140 Costello Dr Winchester VA
$80 nightly
The price is $87 total per night from Apr 26 to Apr 27
$87 total
Apr 26 - Apr 27
Total with taxes and fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.8/10 Good! (1,000 reviews)
I only stayed for about an hour. The room was freezing cold as it was dead of winter and freezing out. There was no heat turned on in the room when I got there so it was quite a while before the room actually reached a tolerable temperature
Reviewed on Mar 26, 2026
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
$88 nightly
The price is $96 total per night from Apr 12 to Apr 13
$96 total
Apr 12 - Apr 13
Total with taxes and fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,455 reviews)
La chambre était bien. Cependant, il y avait une odeur de retour d'air de balayeuse. Le déjeuner était bien, mais j'aurais aimé qu'il y ait des muffins.
Reviewed on Apr 4, 2026
Hampton Inn Winchester-University/Mall Area
640 East Jubal Early Drive Winchester VA
$100 nightly
The price is $113 total per night from Apr 12 to Apr 13
$113 total
Apr 12 - Apr 13
Total with taxes and fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,001 reviews)
Nice lobby, nice room, ample parking, good breakfast selection, good area around the hotel
Reviewed on Mar 15, 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 neighborhoods 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, VA
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