Old Town Winchester Travel Guide
Tourist Guide
Visit Old Town Winchester
Stay near popular Old Town Winchester attractions
Our pick of the best Old Town Winchester Hotel Deals
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
The price is NZ$261 per night from 11 Oct to 12 Oct
NZ$261
11 Oct - 12 Oct
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 ...
9.4/10 Exceptional! (1,000 reviews)
"Clean room, great shower. A block from the walking mall with lots of food, shopping, and a few breweries. Highly recommend."
Reviewed on 28 Sept 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
The price is NZ$138 per night from 5 Oct to 6 Oct
NZ$138
5 Oct - 6 Oct
includes taxes & fees
Stay at this motel in Winchester. Enjoy free parking, a 24-hour front desk and daily housekeeping. Our guests praise the helpful staff and the clean rooms in ...
8.6/10 Excellent! (1,081 reviews)
"Clean room"
Reviewed on 29 Sept 2026
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
The price is NZ$184 per night from 19 Oct to 20 Oct
NZ$184
19 Oct - 20 Oct
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. ...
9.2/10 Wonderful! (1,006 reviews)
"Great hotel. Convenient location, friendly staff, clean environment"
Reviewed on 30 Sept 2026
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
The price is NZ$212 per night from 1 Oct to 2 Oct
NZ$212
1 Oct - 2 Oct
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 ...
Quality Inn Winchester
1601 Martinsburg Pike Winchester VA
The price is NZ$165 per night from 26 Oct to 27 Oct
NZ$165
26 Oct - 27 Oct
includes taxes & fees
Stay at this hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their reviews. ...
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
The price is NZ$201 per night from 25 Oct to 26 Oct
NZ$201
25 Oct - 26 Oct
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! (1,461 reviews)
"This hotel is great, the only thing that could be A LOT better is the water pressure from the shower head."
Reviewed on 30 Sept 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.
Check Old Town Winchester hotel availability
Our guide on 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 Shenandoah Valley Discovery Museum.
