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 ฿4,386 per night from 1 Nov to 2 Nov
฿4,386
฿4,969 total
1 Nov - 2 Nov
includes taxes & fees
Stay at this spa hotel in Winchester. Enjoy free Wi-Fi, a full-service spa and 2 restaurants. Our guests praise the helpful staff and the clean rooms in their ...
9.4/10 Exceptional! (1,001 reviews)
"The staff was just not welcoming or helpful."
Reviewed on 7 Oct 2026
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
The price is ฿2,987 per night from 1 Nov to 2 Nov
฿2,987
฿3,325 total
1 Nov - 2 Nov
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! (1,448 reviews)
"Very clean room. Well-lit parking lot."
Reviewed on 8 Oct 2026
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
The price is ฿2,869 per night from 1 Nov to 2 Nov
฿2,869
฿3,193 total
1 Nov - 2 Nov
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! (1,000 reviews)
"The mattress was excellent. I woke up refreshed without a back ache which I came in with due to the long car ride. My room was quiet, and clean. My only complaint is wondering why there is such a strong smell of air deodorizer throughout the hotel. It hits you as you walk in the lobby. The smell ..."
Reviewed on 7 Oct 2026
Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr Strasburg VA
The price is ฿2,545 per night from 1 Nov to 2 Nov
฿2,545
฿2,832 total
1 Nov - 2 Nov
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 ...
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
The price is ฿3,633 per night from 1 Nov to 2 Nov
฿3,633
฿4,044 total
1 Nov - 2 Nov
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 ...
Comfort Inn & Suites Winchester
195 Kernstown Commons Blvd Winchester VA
The price is ฿3,346 per night from 18 Oct to 19 Oct
฿3,346
฿3,724 total
18 Oct - 19 Oct
includes taxes & fees
Stay at this golf hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their reviews. ...
9.4/10 Exceptional! (1,130 reviews)
"Excellent professional staff, great room"
Reviewed on 6 Oct 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 Bright Box Theater and Shenandoah Valley Discovery Museum.
