Old Town Winchester, VA

Winchester

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

Popular places to visit

Museum of the Shenandoah Valley

Museum of the Shenandoah Valley

5/5(20 reviews)

You can spend time exploring the galleries in Museum of the Shenandoah Valley during your trip to Winchester. Check out the charming coffeehouses or top-notch restaurants in this walkable area.

Museum of the Shenandoah Valley
Jim Barnett Park

Jim Barnett Park

4/5(1 review)

Explore the great outdoors at Jim Barnett Park, a lovely green space in Winchester. Check out the charming coffeehouses or top-notch restaurants in this walkable area.

Jim Barnett Park

Bright Box Theater

4.5/5(4 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.

Bright Box Theater

Shenandoah Valley Discovery Museum

4.5/5(11 reviews)

You can take time to visit Shenandoah Valley Discovery Museum during your travels to Winchester. While in this walkable area, you can savor the top-notch restaurants.

Shenandoah Valley Discovery Museum

Handley Regional Library

5/5(2 reviews)

After visiting Handley Regional Library, make a plan to see the other sights and activities in Winchester. Check out the charming coffeehouses or top-notch restaurants in this walkable area.

Handley Regional Library

George Washington's Office

You can learn about the history of Winchester when you stop by George Washington's Office. While in this walkable area, you can savor the top-notch restaurants.

George Washington's Office

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
$120 nightly
The price is $136 total per night from Jun 14 to Jun 15
$136 total
Jun 14 - Jun 15
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! (1,002 reviews)
"Charming."

Reviewed on Jun 3, 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
$81 nightly
The price is $92 total per night from Jun 28 to Jun 29
$92 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! (1,006 reviews)
"The breakfast was great. Something for everyone including my picky grandson. The pillows and the bed were so comfortable. My daughter and I laughed as we could have stayed in bed all day. lol"

Reviewed on Jun 4, 2026

Spark by Hilton Winchester
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court Winchester VA
$93 nightly
The price is $103 total per night from Jul 5 to Jul 6
$103 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! (910 reviews)
"great visit and would stay again for sure"

Reviewed on Jun 4, 2026

TRU By Hilton Winchester
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike Winchester VA
$71 nightly
The price is $77 total per night from Jun 7 to Jun 8
$77 total
Jun 7 - Jun 8
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! (1,054 reviews)
"The room was very clean and the staff was friendly."

Reviewed on Jun 2, 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
$90 nightly
The price is $98 total per night from Jun 14 to Jun 15
$98 total
Jun 14 - Jun 15
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! (1,462 reviews)
"Excellent stay"

Reviewed on Jun 4, 2026

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
$101 nightly
The price is $110 total per night from Jul 5 to Jul 6
$110 total
Jul 5 - Jul 6
Total with taxes and fees
Book a stay at this 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)
"It was very clean and the bes was super comfortable. Did not eat the breakfast so I don't know how it was. Staff was really friendly"

Reviewed on May 30, 2026

Holiday Inn Winchester Se-Historic Gateway by IHG
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 Shenandoah Valley Discovery Museum.

Old Town Winchester, VA

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