Winchester Travel Guide

Tourist 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 popular for its abundant dining options, and if you're looking for more to see and do, you might think about a trip to Bright Box Theater or Shenandoah Valley Discovery Museum.

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 AU$170 per night from 7 Apr to 8 Apr
AU$170
includes taxes & fees
7 Apr - 8 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! (1,897 reviews)
"Quiet and clean"

Reviewed on 3 Apr. 2025

La Quinta Inn & Suites by Wyndham Winchester
Spark by Hilton Winchester
Spark by Hilton Winchester
3 out of 5
150 Wingate Dr, Winchester, VA
The price is AU$176 per night from 20 Apr to 21 Apr
AU$176
includes taxes & fees
20 Apr - 21 Apr
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and ...
8.8/10 Excellent! (1,001 reviews)
"Everthing was excellent except the breakfast could be improve. It would be nice to have some hot items."

Reviewed on 1 Apr. 2025

Spark by Hilton 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 AU$228 per night from 4 May to 5 May
AU$228
includes taxes & fees
4 May - 5 May
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! (1,000 reviews)
"Beautiful hotel, super easy check in, restaurant on the property is Unos Pizzeria, just one block away is Old Town and we had an enjoyable evening strolling that area after dinner. We’ve already booked another stay for ‘our stop on the way home.’"

Reviewed on 31 Mar. 2025

The George Washington Hotel, A Wyndham Grand Hotel
See all 1,976 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.
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! (275 reviews)
Spectacular Views!
"We thoroughly enjoyed our stay here. From the moment you walk into the cabin, the views are spectacular and the surroundings are relaxing. We had a wonderful time and can’t wait to come back in the warmer weather to enjoy the outdoors more within a quick drive of lots of parks and scenic views Very ..."

Reviewed on 2 Apr. 2025

Star view cabin-Riverfront
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, patios, and an in-room coffeemaker. Popular attractions Frog Valley Artisans, LTD and Colonial Springs ...
9.8/10 Exceptional! (36 reviews)
Anniversary Trip
"We stayed here for our anniversary and had a great time. Hosts were very responsive when we had a question about the hot tub,"

Reviewed on 4 Feb. 2025

Dreamtime - Modern A-frame Cabin w/ Hot tub
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
Harpers Ferry
Stay at this vacation home in Harpers Ferry. Enjoy free WiFi, patios, and an in-room coffeemaker. Our guests praise the helpful staff in our reviews. Popular ...
9.6/10 Exceptional! (92 reviews)
2 Night Stay
"We enjoyed a very comfortable stay. House was very clean and cozy. We were a little surprised by the close proximity to other homes, but other than that it was as described. Hosts were easy to communicate with and created a very welcoming space for us. Thank you!"

Reviewed on 16 Mar. 2025

Riverside cottage, minutes from historic Harpers Ferry! Private river access!
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

Museum of the Shenandoah Valley

Museum of the Shenandoah Valley

You can spend time browsing the exhibits at Museum of the Shenandoah Valley during your trip to Winchester. Visit the cosy cafes or top-notch restaurants in this walkable area.

Museum of the Shenandoah Valley
Handley Regional Library

Handley Regional Library

After visiting Handley Regional Library, make a plan to see the other sights and activities in Winchester. Visit the top-notch restaurants or cosy cafes in this walkable area.

Handley Regional Library

Winchester Medical Center

If Winchester Medical Center is what brings you to town, hopefully you'll have a chance to explore more of Winchester.

Winchester Medical Center

Shenandoah University

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

Shenandoah University

Apple Blossom Mall

You can search for that perfect souvenir at Apple Blossom Mall during your stay in Winchester. While in this walkable area, you can savour 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 savour the top-notch restaurants.

Shenandoah Valley Discovery Museum

Cities near Winchester

Photo by KM Moore

Berryville

Other places like Winchester