Old Town Winchester Travel Guide

Tourist Guide

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

Popular places to visit


Our pick of the best Old Town Winchester Hotel Deals

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 AU$228 per night from 20 Apr to 21 Apr
AU$228
includes taxes & fees
20 Apr - 21 Apr
Stay at this 3.5-star spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the bar and the helpful staff in our ...
9.2/10 Wonderful! (1,006 reviews)
"Beautiful hotel, super easy check in, restaurant on the property is Unos Pizzeria, just one block away is Old Town and we had an enjoyable evening strolling that area after dinner. We’ve already booked another stay for ‘our stop on the way home.’"

Reviewed on 31 Mar. 2025

The George Washington Hotel, A Wyndham Grand Hotel
La Quinta Inn & Suites by Wyndham Winchester
La Quinta Inn & Suites by Wyndham Winchester
2.5 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
The price is AU$156 per night from 6 Apr to 7 Apr
AU$156
includes taxes & fees
6 Apr - 7 Apr
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 ...
9/10 Wonderful! (1,888 reviews)
"The room layout is unique and we love it."

Reviewed on 29 Mar. 2025

La Quinta Inn & Suites by Wyndham Winchester
Spark by Hilton Winchester
Spark by Hilton Winchester
3 out of 5
150 Wingate Dr, Winchester, VA
The price is AU$159 per night from 16 Apr to 17 Apr
AU$159
includes taxes & fees
16 Apr - 17 Apr
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and ...
8.8/10 Excellent! (1,005 reviews)
"Very clean"

Reviewed on 30 Mar. 2025

Spark by Hilton Winchester
Comfort Inn & Suites
Comfort Inn & Suites
2.5 out of 5
195 Kernstown Commons Blvd, Winchester, VA
The price is AU$154 per night from 6 Apr to 7 Apr
AU$154
includes taxes & fees
6 Apr - 7 Apr
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! (1,002 reviews)
"All good!"

Reviewed on 29 Mar. 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 AU$146 per night from 20 Apr to 21 Apr
AU$146
includes taxes & fees
20 Apr - 21 Apr
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! (1,164 reviews)
"The place was amazing comfortable and spotless and the staff was great"

Reviewed on 30 Mar. 2025

Microtel Inn & Suites 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 AU$164 per night from 3 Apr to 4 Apr
AU$164
includes taxes & fees
3 Apr - 4 Apr
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
9/10 Wonderful! (1,001 reviews)
"Very nice staff. Quiet and very clean place."

Reviewed on 24 Mar. 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
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 Winchester Little Theater.

Winchester Historic District

Old Town Winchester Travel Guide

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