Old Town Winchester Travel Guide
Winchester
Visit Old Town Winchester
Stay near popular Old Town Winchester attractions
Things to do
Shenandoah Tour: Self-Guided Drive
฿567
per traveller
98% of travellers recommend
Top hotels in Old Town Winchester
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
The price is ฿4,404 per night from 9 Nov to 10 Nov
฿4,404
฿4,990 total
9 Nov - 10 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 ...
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
The price is ฿2,398 per night from 1 Nov to 2 Nov
฿2,398
฿2,645 total
1 Nov - 2 Nov
includes taxes & fees
Stay at this motel in Winchester. Enjoy free parking, a 24-hour front desk and daily housekeeping. Our guests praise the helpful staff and the clean rooms in ...
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
The price is ฿2,837 per night from 22 Nov to 23 Nov
฿2,837
฿3,158 total
22 Nov - 23 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 ฿2,881 per night from 8 Nov to 9 Nov
฿2,881
฿3,206 total
8 Nov - 9 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! (1,004 reviews)
"Nice"
Reviewed on 27 Oct 2026
Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr Strasburg VA
The price is ฿2,555 per night from 3 Nov to 4 Nov
฿2,555
฿2,844 total
3 Nov - 4 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 ...
8.2/10 Very good! (1,013 reviews)
"This was an amazing surprise 100% in every category. very clean rooms, every area smelled so fresh. Plenty of handicap accessible parking and guest rooms. Hot complimentary breakfast 7 AM - 10 AM; pancake machine, eggs, sausage, choice of bread, muffins, bagels, yogurt and cereals. Juice machine ..."
Reviewed on 26 Oct 2026
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
The price is ฿3,851 per night from 1 Nov to 2 Nov
฿3,851
฿4,286 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 ...
9.2/10 Wonderful! (2,260 reviews)
"This is our favorite stop on our way home to NY from S Car! Friendly staff, comfortable bed, awesome shower, and breakfast before we hit the road. Easy on and off I-81. What more could we ask for ?!"
Reviewed on 28 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.
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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.
