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 ฿4,384 per night from 5 Aug to 6 Aug
฿4,384
฿4,967 total
5 Aug - 6 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! (1,005 reviews)
"Excellent quality hotel , large comfortable room and upgraded bathroom . Throughout the hotel there are a few oddities to remind of how historic the property( like the mail shoot outside the elevators) is and how it’s been brought up to date to meet the modern needs. A great place to stay in Winchester ..."
Reviewed on 18 Jul 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
The price is ฿2,793 per night from 2 Aug to 3 Aug
฿2,793
฿3,209 total
2 Aug - 3 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 ...
9.2/10 Wonderful! (1,005 reviews)
"That hotel was outstanding. It was very clean. The beds and pillows were amazing. Great night sleep. We had the option of adding breakfast in at a reduced cost when I booked it and we are very glad we did. The breakfast was fabulous. Well worth the money."
Reviewed on 18 Jul 2026
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
The price is ฿3,063 per night from 26 Jul to 27 Jul
฿3,063
฿3,409 total
26 Jul - 27 Jul
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. ...
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
The price is ฿3,309 per night from 27 Jul to 28 Jul
฿3,309
฿3,683 total
27 Jul - 28 Jul
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 and the clean rooms ...
9.2/10 Wonderful! (1,434 reviews)
"Overall we enjoyed our stay. The breakfast was excellent- my husband even said it was the best breakfast we had on our entire trip! The young woman who took care of the breakfast area was incredibly sweet, friendly, and kept everything well stocked. The only suggestions we have are a few maintenance ..."
Reviewed on 18 Jul 2026
Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr Strasburg VA
The price is ฿2,715 per night from 2 Aug to 3 Aug
฿2,715
฿3,022 total
2 Aug - 3 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! (1,003 reviews)
"A very decent hotel clean rooms"
Reviewed on 18 Jul 2026
Comfort Inn & Suites Winchester
195 Kernstown Commons Blvd Winchester VA
The price is ฿3,420 per night from 13 Aug to 14 Aug
฿3,420
฿3,807 total
13 Aug - 14 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 ...
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 Winchester Little Theater and Shenandoah Valley Discovery Museum.
