Winchester
Travel Guide
Visit Winchester
Where to stay in Winchester
Find the best Winchester areas for the activities you enjoy most.
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.
Photo by Fernando Begay
Open Photo by Fernando Begay
Winchester Historic District
While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Winchester Little Theater.
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
Fully refundableReserve now, pay when you stay
The price is €89 per night from 26 Jul to 27 Jul
€89
26 Jul - 27 Jul
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. ...
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
The price is €74 per night from 3 Aug to 4 Aug
€74
3 Aug - 4 Aug
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking and a fitness centre. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,010 reviews)
"Great staff, clean rooms and delightful breakfast. I'll be back!"
Reviewed on 5 Jul 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
The price is €87 per night from 2 Aug to 3 Aug
€87
2 Aug - 3 Aug
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (1,012 reviews)
"This is a beautiful B&B. Perfect location & very helpful staff. I highly recommend it."
Reviewed on 10 Jul 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.
Roadhaven1830
355 Orchard Drive Mount Jackson VA
Stay at this apartment in Mount Jackson. Enjoy free parking and a garden. Popular attractions Mt Jackson Thrift & Gift and Meems Bottom Covered Bridge are located ...
9.6/10 Exceptional! (43 reviews)
"Wonderful stay; Olivia, the host is top-notch. Thanks!"
Reviewed on 30 Jun 2026
Dreamtime - Modern A-frame Cabin w/ Hot tub
Berkeley Springs WV
Stay at this cabin in Berkeley Springs. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Frog Valley Artisans, LTD and Colonial Springs Spa ...
10/10 Exceptional! (65 reviews)
"I found the atmosphere cozier and lovely. I really liked it."
Reviewed on 8 Jun 2026
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 coffee maker and in-room fireplaces. Popular attractions Ice House and Berkeley ...
10/10 Exceptional! (90 reviews)
"The house was great! Highly recommend!"
Reviewed on 6 Jul 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.
