Old Town Winchester Travel Guide
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 Rp2.186.655 per night from 16 Aug to 17 Aug
Rp2.186.655
Rp2.477.480 total
16 Aug - 17 Aug
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! (1,018 reviews)
"Great walking location to everything. Fancy historic building."
Reviewed on 9 Aug 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
The price is Rp1.664.421 per night from 13 Aug to 14 Aug
Rp1.664.421
Rp1.906.191 total
13 Aug - 14 Aug
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 ...
9/10 Wonderful! (1,019 reviews)
"They were up grading the cabel nut it wasnt finished so didnt have much to watch when just trying to relax before thr next leg of our trip. Also it was a bit confusing when booked thought had free breakfast but then was told didnt have the upgrade never saw anything when booked with Expedia"
Reviewed on 9 Aug 2026
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
The price is Rp1.379.680 per night from 23 Aug to 24 Aug
Rp1.379.680
Rp1.563.177 total
23 Aug - 24 Aug
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! (1,010 reviews)
"Very good for the price"
Reviewed on 8 Aug 2026
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
The price is Rp1.932.876 per night from 6 Sept to 7 Sept
Rp1.932.876
Rp2.151.291 total
6 Sept - 7 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 ...
Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr Strasburg VA
The price is Rp1.445.183 per night from 16 Aug to 17 Aug
Rp1.445.183
Rp1.608.489 total
16 Aug - 17 Aug
includes taxes & fees
Stay at this business-friendly hotel in Strasburg. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in ...
8.2/10 Very good! (1,004 reviews)
"Everything was great! Did see about 1 or 2 bugs in our room but thats expected when it rains hard. Breakfast was delicious, parking was easily accessible, & check in/check out was seamless. The restaurant attached to the hotel is a great addition and food was amazing. Staff in the restaurant were ..."
Reviewed on 8 Aug 2026
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
The price is Rp1.660.842 per night from 16 Aug to 17 Aug
Rp1.660.842
Rp1.848.517 total
16 Aug - 17 Aug
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 ...
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 Stonewall Jackson's Headquarters.
