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 ฿4,013 per night from 7 Sept to 8 Sept
฿4,013
฿4,547 total
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 ...
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
The price is ฿2,648 per night from 17 Sept to 18 Sept
฿2,648
฿3,000 total
17 Sept - 18 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! (1,015 reviews)
"Very clean and lovely. We enjoyed it"
Reviewed on 20 Aug 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
The price is ฿3,057 per night from 30 Aug to 31 Aug
฿3,057
฿3,501 total
30 Aug - 31 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! (1,017 reviews)
"Room was clean, roomy and comfy. Comfy chair with ottoman was a plus. Air conditioner was noisy. Breakfast is what you get at other hotels for free. $15 here. Bench out front really needs to be cleaned. Covered with bird poop. Friendly and helpful staff"
Reviewed on 20 Aug 2026
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
The price is ฿3,373 per night from 23 Aug to 24 Aug
฿3,373
฿3,754 total
23 Aug - 24 Aug
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 ...
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
The price is ฿2,866 per night from 30 Aug to 31 Aug
฿2,866
฿3,190 total
30 Aug - 31 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 ...
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
The price is ฿3,208 per night from 27 Aug to 28 Aug
฿3,208
฿3,570 total
27 Aug - 28 Aug
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! (1,011 reviews)
"We love Tru ! Everyone is very helpful . Rooms are clean . Easy check in and out . Breakfast is great ! We love stayingvthere !"
Reviewed on 21 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. 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 Shenandoah Valley Discovery Museum and Stonewall Jackson's Headquarters.
