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Featured Old Town Winchester Family Hotels
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St, Winchester, VA
Fully refundableReserve now, pay when you stay
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 ...
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.
Hotels with Pools in Old Town Winchester
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St, Winchester, VA
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! (1,002 reviews)
"Great location! Short walk to Loudon St where all the restaurants and shops are located along with historic sites. Rooms are very nice and upscale."
Reviewed on Jul 7, 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.
Hotels With Connecting Rooms in Old Town Winchester
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St, Winchester, VA
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 ...
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.
Hotels by Star Rating
More Hotel Options
- Boutique Hotels in Old Town Winchester
- Hotels with a Pool in Old Town Winchester
- Hotel Wedding Venues in Old Town Winchester
- Hotels with Hot Tubs in Old Town Winchester
- Historic Hotels in Old Town Winchester
- Casinos in Old Town Winchester
- Resorts & Hotels with Spas in Old Town Winchester
- Romantic Hotels in Old Town Winchester
- Hotels with an Indoor Pool in Old Town Winchester
- Beach Hotels in Old Town Winchester
Old Town Winchester Neighborhoods
Top Points of Interests in Old Town Winchester
- Hotels near Shenandoah Valley Discovery Museum
- Hotels near Bright Box Theater
- Hotels near Old Court House Civil War Museum
- Hotels near Handley Regional Library
- Hotels near George Washington's Office
- Hotels near Hollywood Casino at Charles Town Races
- Hotels near Summit Point Motorsports Park
- Hotels near Shenandoah River
- Hotels near Shenandoah University
- Hotels near George Washington National Forest
- Hotels near Winchester Medical Center
- Hotels near Bluemont Vineyard
- Hotels near Apple Blossom Mall
- Hotels near Museum of the Shenandoah Valley
- Hotels near Rock Harbor Golf Course
- Hotels near Sky Meadows State Park
- Hotels near Cedar Creek Battlefield Foundation
- Hotels near Lost River
- Hotels near Watermelon Park Campground
- Hotels near Jim Barnett Park
Cities near Old Town Winchester
- Berkeley Springs Hotels (30.74 mi)
- Harpers Ferry Hotels (25.15 mi)
- Winchester Hotels (0.01 mi)
- Blue Ridge Mountains Hotels (325.84 mi)
- Front Royal Hotels (18.44 mi)
- Charles Town Hotels (17.89 mi)
- Shenandoah Valley Hotels (60.79 mi)
- Martinsburg Hotels (21.65 mi)
- Appalachian Mountains Hotels (101.75 mi)
- Northern Virginia Hotels (35.96 mi)
- Strasburg Hotels (17.01 mi)
- Boyce Hotels (8.48 mi)
- Hedgesville Hotels (27.07 mi)
- Bluemont Hotels (18.46 mi)
- Stephens City Hotels (7.48 mi)
- Paw Paw Hotels (28.65 mi)
- Linden Hotels (19.61 mi)
- Berryville Hotels (10.07 mi)
- Inwood Hotels (13.74 mi)
- Paris Hotels (16.88 mi)
Car Rentals Near Old Town Winchester
- Car rentals in Berkeley Springs
- Car rentals in Harpers Ferry
- Car rentals in Winchester
- Car rentals in Blue Ridge Mountains
- Car rentals in Front Royal
- Car rentals in Charles Town
- Car rentals in Shenandoah Valley
- Car rentals in Martinsburg
- Car rentals in Appalachian Mountains
- Car rentals in Northern Virginia
- Car rentals in Strasburg
- Car rentals in Boyce
- Car rentals in Hedgesville
- Car rentals in Bluemont
- Car rentals in Stephens City
- Car rentals in Paw Paw
Top Family Hotel Destinations
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Top Booked Hotels in Old Town Winchester
- The George Washington Hotel, A Wyndham Grand Hotel
- La Quinta Inn & Suites by Wyndham Winchester
- Travelodge by Wyndham Winchester
- Holiday Inn Winchester Se-Historic Gateway by IHG
- Days Inn by Wyndham Charles Town/Harpers Ferry
- Country Inn & Suites by Radisson, Winchester, VA
- Ramada by Wyndham Strasburg/Shenandoah Valley
- Hampton Inn Front Royal
- Spark by Hilton Winchester
- Sleep Inn & Suites
- Quality Inn
- Fairfield Inn & Suites by Marriott Winchester