Old Town Winchester, VA
Winchester
Visit Old Town Winchester
Popular places to visit
Handley Regional Library
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
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
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.
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 Jul 28 to Jul 29
SAR 475
SAR 538 total
28 Jul - 29 Jul
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! (1,005 reviews)
"Beautiful suite with fireplace. Unfortunately, was 82 degrees due to poor HVAC. Lovely hotel in a great location. All in all we made it work..,"
Reviewed on 24 July 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 28 to Jul 29
SAR 389
SAR 423 total
28 Jul - 29 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 ...
9.2/10 Wonderful! (2,091 reviews)
"Good overnight stop. Clean"
Reviewed on 25 July 2025
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza, Winchester, VA
The price is SAR 309 per night from Aug 17 to Aug 18
SAR 309
SAR 336 total
17 Aug - 18 Aug
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! (1,318 reviews)
DA BOMB
"IT WAS A VERY NICE HOTEL. GREAT LOCATION & LIKE BRAND NEW (OPEN 3YRS BUT NO WEAR & TEAR).)"
Reviewed on 21 July 2025
Travelodge by Wyndham Winchester
160 Front Royal Pike, Winchester, VA
The price is SAR 263 per night from Jul 28 to Jul 29
SAR 263
SAR 286 total
28 Jul - 29 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. ...
8.4/10 Very Good! (1,096 reviews)
"Hotel was right off highway, very inexpensive, unexpectedly provided light breakfast (waffles, cereal, toast, coffee, juice). Would stay there again."
Reviewed on 23 July 2025
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike, Winchester, VA
The price is SAR 334 per night from Aug 3 to Aug 4
SAR 334
SAR 375 total
3 Aug - 4 Aug
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! (1,019 reviews)
"Overall very good experience."
Reviewed on 23 July 2025
Comfort Inn & Suites
195 Kernstown Commons Blvd, Winchester, VA
The price is SAR 364 per night from Aug 3 to Aug 4
SAR 364
SAR 396 total
3 Aug - 4 Aug
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 breakfast and the helpful ...
9.4/10 Exceptional! (1,015 reviews)
"Love the location and stay here often. My only problem is the mattress is horrible. May be time for an upgrade."
Reviewed on 24 July 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 Winchester Little Theater.
- 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
- Handley Regional Library
- Old Court House Civil War Museum
- George Washington's Office
- Hollywood Casino at Charles Town Races
- Summit Point Motorsports Park
- Shenandoah River
- Winchester Medical Center
- Shenandoah University
- George Washington National Forest
- Bluemont Vineyard
- Museum of the Shenandoah Valley
- Apple Blossom Mall
- Rock Harbor Golf Course
- Sky Meadows State Park
- Lost River
- Cedar Creek Battlefield Foundation
- Jefferson County Courthouse
- Patsy Cline Historic House
- Watermelon Park Campground
- Dinosaur Land
- Cedar Creek and Belle Grove National Historical Park
- Jim Barnett Park
- Belle Boyd Cottage
- Winchester Little Theater
- Belle Grove Plantation
- The Kernstown Battlefield
- Locust Hill Golf Course
- Charles Town Library
- Blue Ridge Shadows Golf Club
- Front Royal Visitor's Center
More Hotel Options in Old Town Winchester
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