Winchester, VA
Travel Guide
Visit Winchester
Where to stay in Winchester
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.
Winchester Historic District
While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Shenandoah Valley Discovery Museum.
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
The price is ￥18,170 per night from Jun 14 to Jun 15
￥18,170
￥19,769 total
Jun 14 - Jun 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 in our reviews. ...
9/10 Wonderful! (901 reviews)
"Room smelled like smoke. Good for run through the town overnight stay"
Reviewed on Jun 2, 2026
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
The price is ￥15,688 per night from Jun 14 to Jun 15
￥15,688
￥17,776 total
Jun 14 - Jun 15
includes taxes & fees
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! (1,030 reviews)
"Bagel buffet ok but prefer eggs and taters."
Reviewed on Jun 1, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
Fully refundableReserve now, pay when you stay
The price is ￥11,335 per night from Jun 3 to Jun 4
￥11,335
￥12,333 total
Jun 3 - Jun 4
includes taxes & fees
Stay at this motel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.6/10 Excellent! (1,050 reviews)
"Good place in Winchester"
Reviewed on Jun 2, 2026
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.
Private, light filled retreat space...
with your own pickleball court!
Berkeley Springs WV
Stay at this cabin in Berkeley Springs. Enjoy cable/satellite TV service, an in-room coffeemaker, and in-room fireplaces. Popular attractions Ice House and Berkeley ...
10/10 Exceptional! (84 reviews)
"We loved our stay! Very private and clean. We even tried pickleball for the first time. Would highly recommend!"
Reviewed on May 31, 2026
Dreamtime - Modern A-frame Cabin w/ Hot tub
Berkeley Springs WV
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! (63 reviews)
"Great cabin! Hot tub was nice, house was very clean"
Reviewed on May 14, 2026
Roadhaven1830
355 Orchard Drive Mount Jackson VA
Stay at this apartment in Mount Jackson. Enjoy free parking, a garden, and premium bedding. Popular attractions Mt Jackson Thrift & Gift and Meems Bottom Covered ...
9.6/10 Exceptional! (40 reviews)
"Very clean close to every and anything local food was amazing and host had a book that showed a lot about the area which came in handy and grounds was so nice games was fun and pit was amazing bed was so comfortable shower pressure was great water was nice an hot too will come back"
Reviewed on Apr 12, 2026
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
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.
Jim Barnett Park
Explore the great outdoors at Jim Barnett Park, a lovely green space in Winchester. Check out the charming coffeehouses or top-notch restaurants in this walkable area.
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.
Patsy Cline Historic House
You can find out about the history of Winchester with a stop at Patsy Cline Historic House. While in this walkable area, you can savor the top-notch restaurants.
Winchester Little Theater
Enjoy a show at Winchester Little Theater, a storied theater in Winchester. While in this walkable area, you can savor the top-notch restaurants.
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.
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