Winchester

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 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 €94 per night from 6 Apr to 7 Apr
€94
includes taxes & fees
6 Apr - 7 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! (1,877 reviews)
"The hotel was easy access, clean and a good value for the price. The room was very modern and had everything needed for an overnight stay."

Reviewed on 25 Mar 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 €89 per night from 13 Apr to 14 Apr
€89
includes taxes & fees
13 Apr - 14 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)
"Great spot to stop for the night while traveling. Just off the highway!"

Reviewed on 17 Mar 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 €133 per night from 13 Apr to 14 Apr
€133
includes taxes & fees
13 Apr - 14 Apr
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)
"Love old historical hotel. This one is always been great. Great location neat walking mall and great shopping and restaurants. Street parking and garage nearby. Staff was great."

Reviewed on 23 Mar 2025

The George Washington Hotel, A Wyndham Grand Hotel
See all 1,935 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! (274 reviews)
5 Stars - Incredible Stay with Stunning Views!
"I recently stayed at this cabin over the weekend, and it was an unforgettable experience. The views were absolutely breathtaking — whether it was sunrise over the mountains or relaxing in the evening with a stunning sunset, the scenery was incredible from every angle.The cabin itself was just as ..."

Reviewed on 15 Mar 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! (323 reviews)
Great
"Amazing view, and very quiet. Exactly what i was looking for."

Reviewed on 3 Mar 2025

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

5/5(1 review)

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

4/5(1 review)

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
Photo by KM Moore

Berryville

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