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.
See properties

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 28 to Jun 29
$138 total
Jun 28 - Jun 29
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! (1,010 reviews)
"Clean room. Staff was helpful"

Reviewed on Jun 15, 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
$72 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! (1,013 reviews)
"Excellent hotel, very clean, nice beds."

Reviewed on Jun 15, 2026

Spark by Hilton Winchester
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court Winchester VA
$69 nightly
The price is $76 total per night from Jul 5 to Jul 6
$76 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! (956 reviews)
"Clean and comfortable"

Reviewed on Jun 16, 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 17 to Jun 18
$76 total
Jun 17 - Jun 18
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! (1,070 reviews)
"The room was clean and comfortable. The breakfast was lacking but did its job. Overall it’s hard to beat if you’re looking for a budget friendly stay. Staff was friendly. The power went out for about an hour around 1:30am. The person on shift wasn’t sure why but said the whole grid was out. I’d stay ..."

Reviewed on Jun 16, 2026

Travelodge by Wyndham Winchester
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

2.5 out of 5
21 Signal Knob Dr Strasburg VA
$81 nightly
The price is $90 total per night from Jul 12 to Jul 13
$90 total
Jul 12 - Jul 13
Total with taxes and fees
Book a stay at this business-friendly hotel in Strasburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (1,008 reviews)
"The bed seemed old, I could feel the metal springs and framing through the mattress padding."

Reviewed on Jun 15, 2026

Ramada by Wyndham Strasburg/Shenandoah Valley
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 28 to Jun 29
$99 total
Jun 28 - Jun 29
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! (1,472 reviews)
"Great staff"

Reviewed on Jun 15, 2026

Microtel 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

Choose one or more items to build your trip:

Explore a world of travel with Expedia