Old Town Winchester, VA

Winchester

The Courthouse in Winchester, Virginia.
Old Town Winchester
Old Town Winchester
Old Town Winchester
Old Town Winchester

Stay near popular Old Town Winchester attractions

Bright Box Theater

3.9/5 (18 reviews)
Enjoy a show at Bright Box Theater, a storied theater in Winchester. While in this walkable area, you can savor the top-notch restaurants.
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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
$122 nightly
The price is $138 total per night from Jun 21 to Jun 22
$138 total
Jun 21 - Jun 22
Total with taxes and 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

The George Washington Hotel, A Wyndham Grand Hotel
Spark by Hilton Winchester

Spark by Hilton Winchester

3 out of 5
150 Wingate Dr Winchester VA
$71 nightly
The price is $81 total per night from Jun 28 to Jun 29
$81 total
Jun 28 - Jun 29
Total with taxes and 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! (1,009 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

Spark by Hilton Winchester
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court Winchester VA
$68 nightly
The price is $75 total per night from Jul 5 to Jul 6
$75 total
Jul 5 - Jul 6
Total with taxes and 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! (944 reviews)
"Clean hotel with friendly staff!"

Reviewed on Jun 13, 2026

TRU By Hilton Winchester
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike Winchester VA
$70 nightly
The price is $76 total per night from Jun 22 to Jun 23
$76 total
Jun 22 - Jun 23
Total with taxes and 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! (1,065 reviews)
"All was fine."

Reviewed on Jun 13, 2026

Travelodge by Wyndham Winchester
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 out of 5
150 Faraday Plaza Winchester VA
$91 nightly
The price is $99 total per night from Jun 17 to Jun 18
$99 total
Jun 17 - Jun 18
Total with taxes and 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! (1,471 reviews)
"The coffee was the best part of breakfast. Very basic and not good! There was no hand soap provided for washing hands in the bathroom and there was a large crack in the tile near the shower. The room was small but fairly clean and efficient. We did not use the pool bc it looked small and kind of ..."

Reviewed on Jun 13, 2026

Microtel Inn & Suites by Wyndham Winchester
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
$123 nightly
The price is $133 total per night from Jun 21 to Jun 22
$133 total
Jun 21 - Jun 22
Total with taxes and 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! (2,285 reviews)
"My room was clean, staff were friendly. Hotel was close to lots of things."

Reviewed on Jun 13, 2026

La Quinta Inn & Suites by Wyndham Winchester
See all 367 properties in Old Town 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.

Where to stay in Old Town Winchester

Find the best Old Town Winchester areas and neighborhoods for the activities you enjoy most. Learn more about Old Town Winchester
Learn more about Old Town Winchester
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.

Old Town Winchester, VA

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