Old Town Winchester
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 €121 per night from 2 Aug to 3 Aug
€121
2 Aug - 3 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! (1,002 reviews)
"Best hotel I’ve stayed in!! Will definitely be booking again each visit to Pa from SC! Clean and classy rooms/bathrooms. Historic charm yet updated/maintained. No jail quality sheets/towels, staff was great, pool and hot tub felt more spa like then traditional indoor hotel pool! Just all around wonderful ..."
Reviewed on 15 Jul 2026
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
The price is €89 per night from 26 Jul to 27 Jul
€89
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. ...
9.2/10 Wonderful! (1,035 reviews)
"A clean room and a comfy bed, friendly staff, and the right location for me."
Reviewed on 15 Jul 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
The price is €84 per night from 2 Aug to 3 Aug
€84
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! (1,001 reviews)
"Clean room, good room amenities. Could use a few more outdoor seating options."
Reviewed on 15 Jul 2026
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
The price is €92 per night from 21 Jul to 22 Jul
€92
21 Jul - 22 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! (1,449 reviews)
"A great place to stop on our way from TN to NJ to break up the trip, or vice versa. Easy on amd off highway, clean, good breakast, nice rooms."
Reviewed on 14 Jul 2026
Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr Strasburg VA
The price is €80 per night from 2 Aug to 3 Aug
€80
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! (1,001 reviews)
"Good experience"
Reviewed on 14 Jul 2026
Comfort Inn & Suites Winchester
195 Kernstown Commons Blvd Winchester VA
The price is €101 per night from 13 Aug to 14 Aug
€101
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 ...
9.4/10 Exceptional! (1,138 reviews)
"Excellent - loved the gentlemen who checked us in - would stay again 100%"
Reviewed on 14 Jul 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.
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 Winchester Little Theater.
