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$172 per night from 18 Feb to 19 Feb
AU$172
includes taxes & fees
18 Feb - 19 Feb
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! (1,808 reviews)
"Clean comfortable room. Great hot breakfast."

Reviewed on 13 Feb. 2025

La Quinta Inn & Suites by Wyndham Winchester
Travelodge by Wyndham Winchester
Travelodge by Wyndham Winchester
2.5 out of 5
160 Front Royal Pike, Winchester, VA
The price is AU$115 per night from 1 Mar to 2 Mar
AU$115
includes taxes & fees
1 Mar - 2 Mar
Stay at this motel in Winchester. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
8.2/10 Very Good! (1,096 reviews)
"Very comfortable and well maintained"

Reviewed on 8 Feb. 2025

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
The price is AU$130 per night from 18 Feb to 19 Feb
AU$130
includes taxes & fees
18 Feb - 19 Feb
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! (1,128 reviews)
"clean"

Reviewed on 13 Feb. 2025

Microtel Inn & Suites by Wyndham Winchester
See all 1,891 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.
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! (321 reviews)
Cozy Cabin, Quiet Getaway
"My friend and I spent the weekend in John's Cozy Cabin to enjoy some time away from our urban settings and focus on writing in a quiet, secluded place. This cabin was just what we were seeking because it was tranquil, isolated, in serene settings in the forest along the Shenandoah River, and it had ..."

Reviewed on 30 Jan. 2025

Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
Cottage w Hot Tub, Pond & Kayaks, Fire Pit, & WiFi
Cottage w Hot Tub, Pond & Kayaks, Fire Pit, & WiFi
Berkeley Springs
Stay at this cabin in Berkeley Springs. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Cacapon State Park and Cacapon Resort State ...
8.8/10 Excellent! (30 reviews)
Peaceful Getaway
"Tony was an amazing host. The property was home-y and very spacious. Perfect place to accommodate 2 couples and 2 children (or adults who are children at heart). It was a nice little getaway in the woods with easy access to the town. If you’re looking for a place for some great R&R, this is your ..."

Reviewed on 15 Dec. 2024

Cottage w Hot Tub, Pond & Kayaks, Fire Pit, & WiFi
18th Century Stone Cottage minutes from historic Middleburg
18th Century Stone Cottage minutes from historic Middleburg
Middleburg
Stay at this cottage in Middleburg. Enjoy free WiFi, a garden, and patios. Popular attractions The Boxwood Winery and National Sporting Library & Museum are ...
9.8/10 Exceptional! (36 reviews)
Everything lovely
"Adorable cottage. Well appointef"

Reviewed on 10 Feb. 2025

18th Century Stone Cottage minutes from historic Middleburg
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 cosy cafes or top-notch restaurants in this walkable area.

Handley Regional Library

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

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

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