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 ฿4,117 per night from 2 Aug to 3 Aug
฿4,117
฿4,664 total
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 ...
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
Fully refundableReserve now, pay when you stay
The price is ฿2,527 per night from 27 Jul to 28 Jul
฿2,527
฿2,788 total
27 Jul - 28 Jul
includes taxes & fees
Stay at this motel in Winchester. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in their reviews. ...
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
The price is ฿2,799 per night from 9 Aug to 10 Aug
฿2,799
฿3,216 total
9 Aug - 10 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 ...
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
The price is ฿3,282 per night from 30 Jul to 31 Jul
฿3,282
฿3,653 total
30 Jul - 31 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 ฿3,127 per night from 3 Aug to 4 Aug
฿3,127
฿3,480 total
3 Aug - 4 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 helpful staff and the clean rooms ...
9.2/10 Wonderful! (1,443 reviews)
"This is a gem. Great location off I81 with a gas station as you drive in or out. Parking waa ample. The property is pristine, we'll lit and quiet. The staff is wonderful and the breakfast had a nice variety of choices."
Reviewed on 25 Jul 2026
Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr Strasburg VA
The price is ฿2,721 per night from 23 Aug to 24 Aug
฿2,721
฿3,028 total
23 Aug - 24 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! (1,005 reviews)
"Cleanliness not great. Floor felt ‘sticky’ and everything really looks worn out."
Reviewed on 25 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.
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.
