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
2.5 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
The price is SAR 371 per night from Apr 2 to Apr 3
SAR 371
SAR 403 total
includes taxes & fees
2 Apr - 3 Apr
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 ...
9/10 Wonderful! (1,844 reviews)
"Very clean, comfortable, and friendly."

Reviewed on 3 March 2025

La Quinta Inn & Suites 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
The price is SAR 300 per night from Mar 9 to Mar 10
SAR 300
SAR 326 total
includes taxes & fees
9 Mar - 10 Mar
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! (1,143 reviews)
Would stay again
"It was comfortable and clean"

Reviewed on 1 March 2025

Microtel Inn & Suites by Wyndham 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 SAR 475 per night from Mar 23 to Mar 24
SAR 475
SAR 538 total
includes taxes & fees
23 Mar - 24 Mar
Stay at this 3.5-star spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the bar and the helpful staff in our ...
9.2/10 Wonderful! (1,002 reviews)
"Solid, quiet building. Short convenient walk to old Town Winchester services. Reasonable, affordable room rates. Pleasant pool, hot tub and weight room. Customer-friendly staff."

Reviewed on 2 March 2025

The George Washington Hotel, A Wyndham Grand Hotel
See all 1,902 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.
Charming mountaintop cabin with hot tub, pool table, and breathtaking views
Charming mountaintop cabin with hot tub, pool table, and breathtaking views
Great Cacapon
Stay at this vacation home in Great Cacapon. Enjoy a garden, a pool table, and patios. Popular attractions Frog Valley Artisans, LTD and Prospect Peak are located ...
9.8/10 Exceptional! (195 reviews)
LOST MY ENGAGEMENT RING!
"We booked the cabin for a weekend get away. The cabin was great. My boyfriend purposed to me and I left the ring at the cabin! Please contact me ASAP!"

Reviewed on 16 February 2025

Charming mountaintop cabin with hot tub, pool table, and breathtaking views
Star view cabin-Riverfront
Star view cabin-Riverfront
Rileyville
Stay at this cabin in Rileyville. Enjoy tennis courts, patios, and an in-room coffeemaker. Our guests praise the property condition in our reviews. Popular attractions ...
9.6/10 Exceptional! (272 reviews)
Exceptional Views
"Our second stay and just as fantastic as the first. The fireplace in winter just adds to the ambiance of this fantastic property. The dogs love the property as well as all of the wildlife that passes through. Despite the severe windstorm, the house remained cozy for all of us. Will definitely be ..."

Reviewed on 17 February 2025

Star view cabin-Riverfront
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
Front Royal
Stay at this cabin in Front Royal. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Glen Manor Vineyards and Shenandoah ...
9.4/10 Exceptional! (322 reviews)
Great
"Amazing view, and very quiet. Exactly what i was looking for."

Reviewed on 3 March 2025

Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
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

5/5(19 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
Staircase at Handley Library

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

Winchester Medical Center

4/5(39 reviews)

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

4.5/5(69 reviews)

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

4/5(105 reviews)

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

Rock Harbor Golf Course

3.5/5(3 reviews)

Enjoy a round of golf in Winchester at Rock Harbor Golf Course. While in this walkable area, you can savor the top-notch restaurants.

Rock Harbor Golf Course

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