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 Winchester Little Theater and Shenandoah Valley Discovery Museum.
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
The price is AU$137 per night from 2 Aug to 3 Aug
AU$137
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 ...
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
The price is AU$131 per night from 30 July to 31 July
AU$131
30 July - 31 July
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. ...
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
The price is AU$198 per night from 30 July to 31 July
AU$198
30 July - 31 July
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 ...
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! (44 reviews)
"Quiet, recently renovated and very cute suite with thoughtful accommodations. The owner was very nice and pleasant 😊We stayed in the Elizabeth suite and would definitely stay again!"
Reviewed on 15 July 2026
Wild And Wonderful Silos
Harpers Ferry WV
Stay at this cabin in Harpers Ferry. Enjoy free Wi-Fi, a sauna and patios. Popular attractions Harpers Ferry National Historical Park and Hollywood Casino at ...
8.2/10 Very good! (24 reviews)
"Pictures on internet were very nice and clean. Upon arriving was a different case property had junk behind the silo walkway was not stable uneven round rocks to walk on especially for the distance from the parking.. upon entering the silo not clean shower contained mold, and mildew dead flies on ..."
Reviewed on 15 June 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! (92 reviews)
"The photos are lovely, but the experience of being there is so much more. We loved it! It was so peaceful and lovely. We watched deer families every night and saw a fox as well. So wonderful to see them enjoy the woods with no fear. There was easy access to town and Cacapon. The area has plenty of ..."
Reviewed on 17 July 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.
