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


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 3.104.273 ₫ per night from 31 Aug to 1 Sept
3.104.273 ₫
3.517.142 ₫ total
31 Aug - 1 Sept
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! (1,000 reviews)
"Bed comfy, dinner delicious. Lovely ambiance in lobby and enjoyed pool."

Reviewed on 10 Aug 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 2.695.712 ₫ per night from 1 Sept to 2 Sept
2.695.712 ₫
2.932.966 ₫ total
1 Sept - 2 Sept
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 ...
9.2/10 Wonderful! (2,120 reviews)
"Liam was GREAT!! In addition to the young person that checked us in! This was a wonderful experience."

Reviewed on 12 Aug 2025

La Quinta 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 2.259.564 ₫ per night from 17 Aug to 18 Aug
2.259.564 ₫
2.537.226 ₫ total
17 Aug - 18 Aug
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! (1,001 reviews)
"Bed comfort"

Reviewed on 12 Aug 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
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 2.080.901 ₫ per night from 1 Sept to 2 Sept
2.080.901 ₫
2.264.021 ₫ total
1 Sept - 2 Sept
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! (1,328 reviews)
"Very quiet, carpets felt somewhat yuckie bc it is a pet place. Air conditioning worked very well."

Reviewed on 12 Aug 2025

Microtel Inn & Suites by Wyndham Winchester
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

2.5 out of 5
21 Signal Knob Dr, GPS: 35 Brandy court, Strasburg, VA
The price is 1.764.299 ₫ per night from 1 Sept to 2 Sept
1.764.299 ₫
1.963.665 ₫ total
1 Sept - 2 Sept
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! (1,000 reviews)
"A great hotel. Would definitely stay here again."

Reviewed on 12 Aug 2025

Ramada by Wyndham Strasburg/Shenandoah Valley
Courtyard by Marriott Winchester

Courtyard by Marriott Winchester

3 out of 5
300 Marriott Drive, Winchester, VA
The price is 2.657.615 ₫ per night from 29 Aug to 30 Aug
2.657.615 ₫
2.891.485 ₫ total
29 Aug - 30 Aug
includes taxes & fees
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free parking, breakfast (surcharge) and a 24-hour fitness centre. Our guests praise the helpful ...
8.8/10 Excellent! (858 reviews)
"Beyond excellent! Highly recommend"

Reviewed on 13 Aug 2025

Courtyard by Marriott 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 Winchester Little Theater.

Winchester Historic District


Old Town Winchester Travel Guide

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