Old Town Winchester
Winchester
Visit Old Town Winchester
Stay near popular Old Town Winchester attractions
Old Town Winchester Hotel Deals
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
The price is CA $171 per night from Jul 12 to Jul 13
CA $171
CA $194 total
Jul 12 - Jul 13
includes taxes & fees
Book a 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 ...
9.4/10 Exceptional! (1,003 reviews)
"The physical structure of this hotel would have put it at 5 stars, but it seems like they have a really nice property here, but don't know how to run it like a really nice hotel. First, the idea that a hotel of this caliber has an UNO pizza as their hotel is just strange. Also, the bar is gorgeous ..."
Reviewed on Jun 11, 2026
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
The price is CA $108 per night from Jul 6 to Jul 7
CA $108
CA $122 total
Jul 6 - Jul 7
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 ...
9/10 Wonderful! (1,008 reviews)
"Best hotel Ive stayed in a while. However, breakfast was weak. Only boiled eggs and no waffle maker? No cranberry juice? No yogurt? It was sugary cereal, fruits, bagels, bread and sausage patties."
Reviewed on Jun 11, 2026
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
The price is CA $107 per night from Jul 5 to Jul 6
CA $107
CA $118 total
Jul 5 - Jul 6
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. ...
9/10 Wonderful! (941 reviews)
"Pool was nice. Room was clean. Staff was awesome."
Reviewed on Jun 12, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
The price is CA $99 per night from Jun 14 to Jun 15
CA $99
CA $108 total
Jun 14 - Jun 15
includes taxes & fees
Stay at this motel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.6/10 Excellent! (1,064 reviews)
"The rooms were dirty. Breakfast was minimal. The coffee was instant pored into the coffee machine. Our drain in the tub was working so slow that taking a shower was filling the tub. When we reported it they said we will make note of it. Not, let us move you or send someone to fix it. We won’t stay ..."
Reviewed on Jun 11, 2026
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
The price is CA $130 per night from Jun 21 to Jun 22
CA $130
CA $141 total
Jun 21 - Jun 22
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 and the clean ...
9.2/10 Wonderful! (1,469 reviews)
"Clean room, friendly staff, other guests were quiet and polite."
Reviewed on Jun 12, 2026
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
The price is CA $171 per night from Jul 1 to Jul 2
CA $171
CA $186 total
Jul 1 - Jul 2
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! (2,284 reviews)
"Enjoyed the pool and workout space very much. Everything was very tidy and felt like it was brand new. Typical hotel breakfast with waffles, eggs, bacon as well as the usual cold selection including hard boiled eggs. Excellent coffee in the lobby for our morning departure."
Reviewed on Jun 10, 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 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 Winchester Little Theater.
