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 AU$212 per night from 28 Oct to 29 Oct
AU$212
28 Oct - 29 Oct
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 AU$138 per night from 8 Nov to 9 Nov
AU$138
8 Nov - 9 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 ...
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
The price is AU$136 per night from 1 Nov to 2 Nov
AU$136
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! (1,001 reviews)
"Everything was good"
Reviewed on 9 Oct 2026
Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr Strasburg VA
The price is AU$117 per night from 25 Oct to 26 Oct
AU$117
25 Oct - 26 Oct
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! (1,020 reviews)
"Helpful, friendly, clean, and a restaurant that is attached but not affiliated with but fabulous!"
Reviewed on 10 Oct 2026
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
The price is AU$172 per night from 18 Oct to 19 Oct
AU$172
18 Oct - 19 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 ...
Comfort Inn & Suites Winchester
195 Kernstown Commons Blvd Winchester VA
The price is AU$159 per night from 18 Oct to 19 Oct
AU$159
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! (1,132 reviews)
"Only thing was a negative the breakfast was only open til 9 am. 9:30 or 10 am would have been better"
Reviewed on 9 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.
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.
