Old Town Winchester
Winchester
Visit Old Town Winchester
Stay near popular Old Town Winchester attractions
Top hotels in Old Town Winchester
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
The price is €120 per night from 7 Sept to 8 Sept
€120
7 Sept - 8 Sept
includes taxes & fees
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 clean rooms ...
Nostalgia Lane in the heart of the city
Winchester VA
The price is €284 per night from 31 Aug to 1 Sept
€284
31 Aug - 1 Sept
includes taxes & fees
Stay at this apartment in Winchester. Enjoy laundry facilities, an in-room coffee maker and air conditioning. Popular attractions Bright Box Theater and Old ...
9.2/10 Wonderful! (18 reviews)
"Perfect location for exploring Winchester. Beautiful rooms. Clean and comfortable."
Reviewed on 27 Jul 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
The price is €98 per night from 27 Sept to 28 Sept
€98
27 Sept - 28 Sept
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
The price is €66 per night from 31 Aug to 1 Sept
€66
31 Aug - 1 Sept
includes taxes & fees
Stay at this motel in Winchester. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in their reviews. ...
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
Fully refundableReserve now, pay when you stay
The price is €104 per night from 1 Sept to 2 Sept
€104
1 Sept - 2 Sept
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
The price is €75 per night from 28 Sept to 29 Sept
€75
28 Sept - 29 Sept
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking and a fitness centre. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,004 reviews)
"Having Breakfast is a plus. Clean and quiet = Good"
Reviewed on 29 Aug 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 for the activities you enjoy most.
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 Bright Box Theater and Winchester Little Theater.
