Old Town Winchester, VA
Winchester
Visit Old Town Winchester
Popular places to visit
Handley Regional Library
5/5(2 reviews)
After visiting Handley Regional Library, make a plan to see the other sights and activities in Winchester. Check out the charming coffeehouses or top-notch restaurants in this walkable area.
Museum of the Shenandoah Valley
5/5(19 reviews)
You can spend time exploring the galleries in Museum of the Shenandoah Valley during your trip to Winchester. Check out the charming coffeehouses or top-notch restaurants in this walkable area.
Shenandoah Valley Discovery Museum
4.5/5(11 reviews)
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
4.5/5(4 reviews)
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.
George Washington's Office
You can learn about the history of Winchester when you stop by George Washington's Office. While in this walkable area, you can savor the top-notch restaurants.
Old Town Winchester Hotel Deals
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St, Winchester, VA
The price is SAR 475 per night from Jun 22 to Jun 23
SAR 475
SAR 539 total
22 Jun - 23 Jun
includes taxes & fees
Stay at this 3.5-star spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the bar and the helpful staff in our ...
9.2/10 Wonderful! (1,000 reviews)
"Perfect hotel in a great location!!!"
Reviewed on 4 June 2025
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East, Winchester, VA
The price is SAR 389 per night from Jul 6 to Jul 7
SAR 389
SAR 424 total
6 Jul - 7 Jul
includes taxes & fees
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (2,048 reviews)
"Needed a place to sleep for the night with two kids. Room was spacious, clean, comfy. Kids enjoyed the pool (even though it’s not heated) I was able to blast the AC - and use the black out shades. That’s my favorite part of hotels! La Quinta doesn’t disappoint"
Reviewed on 12 June 2025
Travelodge by Wyndham Winchester
160 Front Royal Pike, Winchester, VA
The price is SAR 259 per night from Jul 2 to Jul 3
SAR 259
SAR 282 total
2 Jul - 3 Jul
includes taxes & fees
Stay at this motel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in our reviews. ...
8.2/10 Very Good! (1,100 reviews)
"Everything I expected"
Reviewed on 14 June 2025
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike, Winchester, VA
The price is SAR 349 per night from Jun 22 to Jun 23
SAR 349
SAR 391 total
22 Jun - 23 Jun
includes taxes & fees
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
9/10 Wonderful! (1,003 reviews)
"Easy to get to very clean great service"
Reviewed on 12 June 2025
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza, Winchester, VA
The price is SAR 321 per night from Jul 6 to Jul 7
SAR 321
SAR 350 total
6 Jul - 7 Jul
includes taxes & 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! (1,257 reviews)
"The hotel is an inexpensive, but well-designed hotel. The room easily accommodated two queen beds and included a microwave, etc. The folks at the front desk were warm and welcoming. The problem was breakfast. I opened the cover to find that, at 8:00 a.m., there was neither eggs nor bacon and had ..."
Reviewed on 14 June 2025
Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr, GPS: 35 Brandy court, Strasburg, VA
The price is SAR 268 per night from Jun 22 to Jun 23
SAR 268
SAR 298 total
22 Jun - 23 Jun
includes taxes & fees
Book a stay at this business-friendly hotel in Strasburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8/10 Very Good! (1,004 reviews)
"Nice quiet stay. Easy to get to."
Reviewed on 14 June 2025
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.
- Places of interest
- Old Town Winchester Hotels by Star Rating
- More Hotel Options in Old Town Winchester
- Hotels in top Winchester neighborhoods
- Old Town Winchester Hotels by Brand
- Shenandoah Valley Discovery Museum
- Bright Box Theater
- Old Court House Civil War Museum
- Handley Regional Library
- George Washington's Office
- Hollywood Casino at Charles Town Races
- Shenandoah University
- Summit Point Motorsports Park
- Shenandoah River
- George Washington National Forest
- Winchester Medical Center
- Bluemont Vineyard
- Museum of the Shenandoah Valley
- Apple Blossom Mall
- Rock Harbor Golf Course
- Jim Barnett Park
- Lost River
- Front Royal Visitor's Center
- Sky Meadows State Park
- Watermelon Park Campground
- Patsy Cline Historic House
- Valerie Hill Winery
- Dinosaur Land
- Jefferson County Courthouse
- The Kernstown Battlefield
- Mt Hebron Cemetery
- Belle Grove Plantation
- Winchester-Frederick County Convention & Visitors Bureau
- Winchester Little Theater
- Locust Hill Golf Course
- Cedar Creek and Belle Grove National Historical Park
- Bing Crosby Stadium
More Hotel Options in Old Town Winchester
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- Golf Hotels in Old Town Winchester
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- Hotel Wedding Venues in Old Town Winchester
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- Hotels with a Pool in Old Town Winchester
- Hotels with an Indoor Pool in Old Town Winchester
- Luxury Hotels in Old Town Winchester
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- Ski Hotels in Old Town Winchester