Old Town Winchester, VA
Winchester
Visit Old Town Winchester
Stay near popular Old Town Winchester attractions
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 Aug 9 to Aug 10
$138 total
Aug 9 - Aug 10
Total with taxes and fees
Book a stay at this spa hotel in Winchester. Enjoy a full-service spa, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$70 nightly
The price is $77 total per night from Aug 2 to Aug 3
$77 total
Aug 2 - Aug 3
Total with taxes and fees
Stay at this motel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.6/10 Excellent! (1,043 reviews)
"W"
Reviewed on Jul 31, 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
$90 nightly
The price is $100 total per night from Aug 30 to Aug 31
$100 total
Aug 30 - Aug 31
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 ...
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
$65 nightly
The price is $73 total per night from Aug 16 to Aug 17
$73 total
Aug 16 - Aug 17
Total with taxes and fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and ...
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
$106 nightly
The price is $118 total per night from Aug 9 to Aug 10
$118 total
Aug 9 - Aug 10
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 in our reviews. ...
9.2/10 Wonderful! (1,004 reviews)
"This was a great location and the breakfast each morning was an added perk. The staff were always very polite, helpful and friendly. I really enjoyed staying here. The room was spacious and very clean, it also had everything I need to make my stay that much enjoyable. Located in a great location, ..."
Reviewed on Aug 1, 2026
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
$109 nightly
The price is $121 total per night from Aug 2 to Aug 3
$121 total
Aug 2 - Aug 3
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! (2,261 reviews)
"Nice room! Location just ok"
Reviewed on Aug 1, 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.
Where to stay in Old Town Winchester
Find the best Old Town Winchester areas and neighborhoods for the activities you enjoy most. Learn more about Old Town Winchester
Learn more about Old Town Winchester
Photo by Fernando Begay
Open Photo by Fernando Begay
Winchester Historic District
While visiting Winchester Historic District, you might make a stop by sights like Winchester Little Theater and Shenandoah Valley Discovery Museum.
Old Town Winchester, VA
Explore a world of travel with Expedia
- B&B in Winchester
- Hotels with Bars in Winchester
- Front Royal Hotels
- Family Hotels in Winchester
- Apartments in Winchester
- Casino Hotels in Winchester
- Leesburg Hotels
- Extended Stay Hotels in Winchester
- Hotels with Hot Tubs in Winchester
- Golf Hotels in Winchester
- Hotels with an Outdoor Pool in Winchester
- Historic Hotels in Winchester
- Hotels with smoking rooms in Winchester
- Hotels with Connecting Rooms in Winchester
- Hotels near Shenandoah University
- Cheap Hotels in Winchester
- Luxury Hotels in Winchester
- Hotels with an Indoor Pool in Winchester
- Hotels with Balconies in Winchester
- Old Town Winchester Hotels
- Hotel Wedding Venues Hotels in Winchester
- Historic Hotels in Old Town Winchester
- Motels in Winchester
- 5 Star Hotels in Winchester
- Hotels with Early Check-in in Winchester
- Hotels with Restaurants in Winchester
- Cabin Rentals in Winchester
- Best Western Hotels in Winchester
- Cottages in Winchester
- Honeymoon Resorts & in Winchester
- 4 Star Hotels in Winchester
- Resorts in Winchester
- Hotels with a View in Winchester
- Hotels with Free Breakfast in Winchester
- Hotels near Washington Dulles Intl.
- Hotels with Kitchenettes in Winchester
- Resorts & Hotels with Spas in Winchester
- Romantic Hotels in Winchester
- Winchester Hotels
- Boutique Hotels in Winchester
- Winery Hotels in Winchester
- Pet-Friendly Hotels in Winchester
- Flights from San Francisco (SFO) to Washington (IAD)
- Flights from Washington Dulles Intl.
- Flights to Washington Dulles Intl.
- Flights to Syria
- Flights to Winchester
- Flights from Richmond (RIC) to Winchester (WGO)
- Flights from Boston (BOS) to Washington (IAD)
- Flights from Dallas (DFW) to Washington (IAD)
- Flights from Winchester
- Flights from Winchester Regional
- Flights from Atlanta (ATL) to Washington (IAD)
- Flights from Denver (DEN) to Washington (IAD)
- Flights from Los Angeles (LAX) to Washington (IAD)
- Visit Bluemont
- Patsy Cline Historic House
- Bright Box Theater
- Visit Marshall
- Visit Front Royal
- Visit Middleburg
- Great Falls Park
- Visit Cross Junction
- Visit Linden
- Visit Upperville
- Visit Bentonville
- Visit Round Hill
- Visit Winchester
- Visit Huntly
- Visit Boyce
- Visit Gore
- Visit Strasburg
- Visit Ashburn
- Visit Fort Valley
- Visit Paris
- Visit Purcellville
- Visit Berryville
- Visit Toms Brook
- Visit Middletown
- Visit Loudoun County
- Visit Star Tannery
- Visit Stephens City
- Visit Millwood
- Shenandoah Valley Discovery Museum
- Visit Lovettsville
- Visit Hume
- Visit Maurertown
- Visit White Post
- Visit Delaplane
- Hertz Rental Cars in Winchester
- Avis Rental Cars in Winchester
- Budget Rental Cars in Winchester
- Enterprise Rental Cars in Winchester
- Thrifty Car Rental Rental Cars in Winchester
- Rent A Wreck Rental Cars in Winchester
- Car rental Winchester
- Rental cars Washington Dulles Intl. airport
- Minivan Car Rentals in Winchester
