Old Town Winchester Travel Guide

Winchester

Old Town Winchester
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby

Popular places to visit

Things to do


Top hotels in Old Town Winchester

The George Washington Hotel, A Wyndham Grand Hotel
The George Washington Hotel, A Wyndham Grand Hotel
3.5 out of 5
103 E Piccadilly St, Winchester, VA
The price is Rp2.054.010 per night from 20 Jul to 21 Jul
Rp2.054.010
Rp2.327.192 total
20 Jul - 21 Jul
includes taxes & fees
Stay at this 3.5-star spa hotel in Winchester. Enjoy free Wi-Fi, a full-service spa and 2 restaurants. Our guests praise the bar and the helpful staff in their ...
9.2/10 Wonderful! (1,002 reviews)
"Great location! Short walk to Loudon St where all the restaurants and shops are located along with historic sites. Rooms are very nice and upscale."

Reviewed on 7 Jul 2025

The George Washington Hotel, A Wyndham Grand Hotel
La Quinta Inn & Suites by Wyndham Winchester
La Quinta Inn & Suites by Wyndham Winchester
3 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
The price is Rp1.879.828 per night from 20 Jul to 21 Jul
Rp1.879.828
Rp2.045.252 total
20 Jul - 21 Jul
includes taxes & fees
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (2,078 reviews)
"Walk in shower convenient. The pillows are uncomfortable, lumpy."

Reviewed on 10 Jul 2025

La Quinta Inn & Suites by Wyndham Winchester
Travelodge by Wyndham Winchester
Travelodge by Wyndham Winchester
2.5 out of 5
160 Front Royal Pike, Winchester, VA
The price is Rp1.119.042 per night from 16 Jul to 17 Jul
Rp1.119.042
Rp1.217.647 total
16 Jul - 17 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 breakfast and the helpful staff in their reviews. ...
8.4/10 Very Good! (1,100 reviews)
"Staff friendly and helpful.. room was clean and bed very comfortable."

Reviewed on 9 Jul 2025

Travelodge by Wyndham Winchester
Holiday Inn Winchester Se-Historic Gateway by IHG
Holiday Inn Winchester Se-Historic Gateway by IHG
3 out of 5
333 Front Royal Pike, Winchester, VA
The price is Rp1.443.402 per night from 27 Jul to 28 Jul
Rp1.443.402
Rp1.619.205 total
27 Jul - 28 Jul
includes taxes & fees
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the breakfast and the ...
9/10 Wonderful! (1,002 reviews)
"Staff was courteous and helpful."

Reviewed on 9 Jul 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
Comfort Inn & Suites
Comfort Inn & Suites
2.5 out of 5
195 Kernstown Commons Blvd, Winchester, VA
The price is Rp1.571.524 per night from 27 Jul to 28 Jul
Rp1.571.524
Rp1.709.819 total
27 Jul - 28 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 breakfast and the helpful staff ...
9.4/10 Exceptional! (1,006 reviews)
"Lobby temp TOO COLD!"

Reviewed on 10 Jul 2025

Comfort Inn & Suites
Microtel Inn & Suites by Wyndham Winchester
Microtel Inn & Suites by Wyndham Winchester
2.5 out of 5
150 Faraday Plaza, Winchester, VA
The price is Rp1.453.133 per night from 20 Jul to 21 Jul
Rp1.453.133
Rp1.581.009 total
20 Jul - 21 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 ...
9/10 Wonderful! (1,296 reviews)
Great place for not a lot of money
"This was a great place to stay for anyone looking for a clean and very comfortable room at a low cost. I did not think you could still get a decent room for $100 a night but this hotel proved me wrong. The room was very clean and comfortable. The continental breakfast was good, nothing fancy but ..."

Reviewed on 10 Jul 2025

Microtel Inn & Suites by Wyndham Winchester
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.

Other neighbourhoods around Old Town Winchester

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Winchester Historic District

While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Shenandoah Valley Discovery Museum.

Winchester Historic District

Old Town Winchester Travel Guide