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 top-notch restaurants or charming coffeehouses 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 top-notch restaurants or charming coffeehouses 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 447 per night from May 11 to May 12
SAR 447
SAR 507 total
includes taxes & fees
11 May - 12 May
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)
Fabulous
"Historical hotel in heart of Winchester, steps from Old Town. Really felt luxurious ~ credit to all involved. Keep up the good work."
Reviewed on 15 April 2025
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East, Winchester, VA
The price is SAR 351 per night from Apr 20 to Apr 21
SAR 351
SAR 382 total
includes taxes & fees
20 Apr - 21 Apr
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 ...
9/10 Wonderful! (1,934 reviews)
"Was easy to check in. Only took a few minutes. The lady at the desk was very nice and helpful. I would definitely stay here again."
Reviewed on 14 April 2025
Comfort Inn & Suites
195 Kernstown Commons Blvd, Winchester, VA
The price is SAR 367 per night from May 11 to May 12
SAR 367
SAR 399 total
includes taxes & fees
11 May - 12 May
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! (1,006 reviews)
"Hotel was located in a convenient spot for dining and shopping however you can hear traffic from the highway. Room was clean and updated. Staff helpful."
Reviewed on 17 April 2025
Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr, GPS: 35 Brandy court, Strasburg, VA
Fully refundableReserve now, pay when you stay
The price is SAR 274 per night from Apr 30 to May 1
SAR 274
SAR 305 total
includes taxes & fees
30 Apr - 1 May
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! (1,000 reviews)
"Nice hotels"
Reviewed on 13 April 2025
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike, Winchester, VA
The price is SAR 336 per night from May 11 to May 12
SAR 336
SAR 377 total
includes taxes & fees
11 May - 12 May
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! (1,000 reviews)
"Nice place with great staff restaurant on site"
Reviewed on 5 April 2025
Spark by Hilton Winchester
150 Wingate Dr, Winchester, VA
The price is SAR 338 per night from May 11 to May 12
SAR 338
SAR 383 total
includes taxes & fees
11 May - 12 May
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and ...
8.8/10 Excellent! (1,000 reviews)
"Quality hotel and affordable. It must be the best kept secret in Winchester! We really don’t have money to spend frivolously and I never heard of the ‘Spark’ brand before. We took a chance and am so happy we did! You won’t regret it!"
Reviewed on 13 April 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
- Handley Regional Library
- Old Court House Civil War Museum
- George Washington's Office
- Hollywood Casino at Charles Town Races
- Shenandoah University
- Shenandoah River
- George Washington National Forest
- Winchester Medical Center
- Summit Point Motorsports Park
- Apple Blossom Mall
- Bluemont Vineyard
- Museum of the Shenandoah Valley
- Rock Harbor Golf Course
- Jim Barnett Park
- Sky Meadows State Park
- Lost River
- Dinosaur Land
- Mackintosh Fruit Farm
- Jefferson County Courthouse
- Cedar Creek Battlefield Foundation
- Winchester Little Theater
- Front Royal Visitor's Center
- Belle Grove Plantation
- Valerie Hill Winery
- Blue Ridge Shadows Golf Club
- Stonewall Jackson's Headquarters
- Patsy Cline Historic House
- Locust Hill Golf Course
- Peacemaker National Training Center
- Virginia River Trips
More Hotel Options in Old Town Winchester
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- Golf Hotels in Old Town Winchester
- Historic Hotels in Old Town Winchester
- Hotel Wedding Venues in Old Town Winchester
- Hotels with Bars in Old Town Winchester
- Hotels with Hot Tubs in Old Town Winchester
- Hotels with WiFi in Old Town Winchester
- Hotels with a Pool in Old Town Winchester
- Hotels with an Indoor Pool in Old Town Winchester
- Luxury Hotels in Old Town Winchester
- Resorts & Hotels with Spas in Old Town Winchester
- Romantic Hotels in Old Town Winchester
- Shopping Hotels in Old Town Winchester
- Ski Hotels in Old Town Winchester