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 Winchester Little Theater and Stonewall Jackson's Headquarters.
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
The price is S$136 per night from 12 Aug to 13 Aug
S$136
12 Aug - 13 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! (1,013 reviews)
"Good location and clean hotel"
Reviewed on 4 Aug, 2026
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
The price is S$112 per night from 17 Aug to 18 Aug
S$112
17 Aug - 18 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 ...
9.2/10 Wonderful! (1,005 reviews)
"It was a great place to stay for our vacation."
Reviewed on 5 Aug, 2026
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
The price is S$177 per night from 16 Aug to 17 Aug
S$177
16 Aug - 17 Aug
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! (1,010 reviews)
"Well, first evening our suites A/C didnt work (80 degrees) and we had to change to a double full size bedroom from our King Suite. The following day we had moved into a new suite but it also wouldn't get any cooler than 74 degrees. That said we had been locked out of our room 3 times due to the card ..."
Reviewed on 4 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.
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! (46 reviews)
"Everything was well decorated and clean. The place was quiet except that it is right by Rt. 81. The property is maintained well but if you want to enjoy their lovely and spacious yard bring mosquito repellent as I was bitten several times. My husband in the other hand had a great time on the swing ..."
Reviewed on 1 Aug, 2026
Canal Cabins
143 Louie's Ln Paw Paw WV
Stay at this cabin in Paw Paw. Enjoy free Wi-Fi, free parking and daily housekeeping. Popular attractions Paw Paw Tunnel and Sideling Hill Wildlife Management ...
9.8/10 Exceptional! (16 reviews)
"A great place for a nice getaway. The place is well tailored for the cyclists."
Reviewed on 5 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.
