Winchester Travel Guide
Tourist Guide
Visit Winchester
Our guide on 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 Shenandoah Valley Discovery Museum or Bright Box Theater.
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 Shenandoah Valley Discovery Museum and Stonewall Jackson's Headquarters.
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
The price is AU$122 per night from 13 Sept to 14 Sept
AU$122
13 Sept - 14 Sept
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 ...
9.2/10 Wonderful! (1,001 reviews)
"Affordable, convenient,"
Reviewed on 2 Sept 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
The price is AU$161 per night from 6 Sept to 7 Sept
AU$161
6 Sept - 7 Sept
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 ...
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
The price is AU$206 per night from 8 Sept to 9 Sept
AU$206
8 Sept - 9 Sept
includes taxes & fees
Stay at this spa hotel in Winchester. Enjoy a full-service spa, 2 restaurants and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms ...
9.4/10 Exceptional! (1,000 reviews)
"Fine"
Reviewed on 1 Sept 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 Wi-Fi, free parking and a garden. Popular attractions Mt Jackson Thrift & Gift and Meems Bottom Covered Bridge ...
9.6/10 Exceptional! (49 reviews)
"5 night stay. Comphy bed and well stocked with pillows, towels and essentials. Quiet lovely surrounding grounds. Easy check in and departure. Close to route 11 for the yard crawl and things to do!"
Reviewed on 17 Aug 2026
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
Rileyville VA
Stay at this cabin in Rileyville. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Chalybeate Spring and Fort Valley Public Library are located ...
9.8/10 Exceptional! (333 reviews)
"The property was clean and homie. We immediately felt relaxed as soon as we walked in. We had plenty to do in the house, even with the bit of rain we had - our kids had their pick at board games . Would definitely recommend and book again!"
Reviewed on 9 Aug 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! (68 reviews)
"Great cabin, super cute and very comfortable, host was very responsive!"
Reviewed on 8 Aug 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.
