Old Town Winchester
Winchester
Visit Old Town Winchester
Stay near popular Old Town Winchester attractions
Things to do
Sunday Funday Loudoun 2 Winery Tour from DC Metro or Leesburg
CA $141
per adult
Shenandoah Tour: Self-Guided Drive
CA $24
per traveller
98% of travellers recommend
Old Town Winchester Hotel Deals
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
The price is CA $182 per night from Nov 9 to Nov 10
CA $182
CA $206 total
Nov 9 - Nov 10
includes taxes & fees
Book a stay at this spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
The price is CA $98 per night from Dec 1 to Dec 2
CA $98
CA $108 total
Dec 1 - Dec 2
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 ...
8.6/10 Excellent! (1,070 reviews)
"Lit et oreillers confortables, par contre le climatiseur ou ventilation de la chambre très bruyant."
Reviewed on Nov 2, 2026
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
The price is CA $115 per night from Nov 8 to Nov 9
CA $115
CA $128 total
Nov 8 - Nov 9
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and ...
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
The price is CA $116 per night from Nov 11 to Nov 12
CA $116
CA $129 total
Nov 11 - Nov 12
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr Strasburg VA
The price is CA $106 per night from Nov 9 to Nov 10
CA $106
CA $118 total
Nov 9 - Nov 10
includes taxes & fees
Book a stay at this business-friendly hotel in Strasburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.2/10 Very good! (1,022 reviews)
"Staff was helpful"
Reviewed on Nov 1, 2026
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
The price is CA $145 per night from Nov 15 to Nov 16
CA $145
CA $161 total
Nov 15 - Nov 16
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (2,272 reviews)
"Arrived late. Staff member at desk very friendly and welcoming. Morning staff very friendly. Room spacious liked the floor plan"
Reviewed on Nov 3, 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.
Check Old Town Winchester hotel availability
Where to stay in Old Town Winchester
Find the best Old Town Winchester areas and neighborhoods 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.
