Winchester, VA

Travel Guide

Winchester
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby

Where to stay in Winchester

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Old Town Winchester

Old Town Winchester is known for its ample dining options, and you can make a stop by Bright Box Theater and Shenandoah Valley Discovery Museum while in the area.

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
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 ￥15,164 per night from Sep 1 to Sep 2
￥15,164
￥16,499 total
Sep 1 - Sep 2
includes taxes & fees
Stay at this 3-star 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! (2,121 reviews)
"Pet friendly, wonderful breakfast, clean, and great staff."

Reviewed on Aug 13, 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 ￥12,711 per night from Aug 24 to Aug 25
￥12,711
￥14,273 total
Aug 24 - Aug 25
includes taxes & fees
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)
"Bed comfort"

Reviewed on Aug 12, 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 ￥11,657 per night from Sep 14 to Sep 15
￥11,657
￥12,682 total
Sep 14 - Sep 15
includes taxes & 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 ...
9/10 Wonderful! (1,328 reviews)
"Very quiet, carpets felt somewhat yuckie bc it is a pet place. Air conditioning worked very well."

Reviewed on Aug 12, 2025

Microtel Inn & Suites by Wyndham Winchester
See all 1,993 properties in 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.
Canal Cabins

Canal Cabins

3 out of 5
143 Louie's Ln, Paw Paw, WV
Stay at this 3-star cabin in Paw Paw. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Paw Paw Tunnel and Chesapeake and Ohio Canal ...
9.6/10 Exceptional! (8 reviews)
"Very nice"

Reviewed on Aug 9, 2025

Canal Cabins
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub

Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub

Edinburg
Stay at this vacation home in Woodstock. Enjoy a garden, laundry facilities, and patios. Popular attractions Shenandoah Vineyards and Edinburg Mill Museum are ...
9.8/10 Exceptional! (322 reviews)
"Lovely cabin in the woods perfect for our family for a relaxing vacation enjoying nature. Beautiful place to view the sunset from the porch."

Reviewed on Aug 10, 2025

Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub
Dreamtime - Modern A-frame Cabin w/ Hot tub

Dreamtime - Modern A-frame Cabin w/ Hot tub

Berkeley Springs
Stay at this cabin in Berkeley Springs. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Frog Valley Artisans, LTD and Colonial Springs Spa ...
10/10 Exceptional! (45 reviews)
"Cutest little house in the woods. We enjoyed the hot tub under the stars, and the very comfortable bed. It was quiet and relaxing in this home, and it was so nice to have the essentials provided (like coffee, sugar, creamer, garbage bags, paper towels, detergent). Very close to the brewery, and to ..."

Reviewed on Jul 16, 2025

Dreamtime - Modern A-frame Cabin w/ Hot tub
See all properties in 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.

Popular places to visit

Gardens at Glen Burnie House.

Museum of the Shenandoah Valley

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

Museum of the Shenandoah Valley
Staircase at Handley Library

Handley Regional Library

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

Handley Regional Library

Winchester Medical Center

Though Winchester Medical Center might be what brings you to town, perhaps you'll have a chance to explore more of Winchester while you are here.

Winchester Medical Center

Shenandoah University

Enjoy the collegiate vibe when you visit Shenandoah University, during your trip to Winchester. While in this walkable area, you can savor the top-notch restaurants.

Shenandoah University

Apple Blossom Mall

You can enjoy retail therapy at Apple Blossom Mall during your visit to Winchester. While in this walkable area, you can savor the top-notch restaurants.

Apple Blossom Mall

Shenandoah Valley Discovery Museum

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

Cities near Winchester

Photo by Fernando Begay

Front Royal

Berkeley Springs State Park which includes a park

Berkeley Springs

Other places like Winchester