Winchester
Travel Guide
Visit Winchester
Where to stay in Winchester
Find the best Winchester areas and neighborhoods for the activities you enjoy most.
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.
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 Stonewall Jackson's Headquarters.
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
The price is CA $130 per night from Aug 12 to Aug 13
CA $130
CA $149 total
Aug 12 - Aug 13
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
9/10 Wonderful! (1,014 reviews)
"Had to go back to desk 2 times after checking in while my wife stood outside our room with luggage in the hall because the keys didn't work. Very frustrating! Also, only 7 channels worked on the TV, was told this was Comcast fault."
Reviewed on Aug 6, 2026
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
The price is CA $108 per night from Aug 23 to Aug 24
CA $108
CA $122 total
Aug 23 - Aug 24
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 ...
9.2/10 Wonderful! (1,005 reviews)
"It was a great place to stay for our vacation."
Reviewed on Aug 5, 2026
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
The price is CA $171 per night from Aug 13 to Aug 14
CA $171
CA $194 total
Aug 13 - Aug 14
includes taxes & fees
Book a 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 ...
9.4/10 Exceptional! (1,012 reviews)
"Beautiful old hotel with easy walking distance to downtown"
Reviewed on Aug 6, 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.
Silo Tiny House Cabin
Harpers Ferry WV
Stay at this cabin in Harpers Ferry. Enjoy free WiFi, a sauna, and patios. Popular attractions Harpers Ferry National Historical Park and Hollywood Casino at ...
8.2/10 Very good! (26 reviews)
"Pros- close to activities, cute home, large outdoor area, supplied coffee & variety of shower soaps. Great water pressure in shower. Fire pit was nice, need to take kindling. Bathrobes provided. Cons- stairs are treacherous. Railing is not attached properly. Weeds are taking over property. Walkway ..."
Reviewed on Jul 11, 2026
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub
Edinburg VA
Stay at this vacation home in Woodstock. Enjoy a garden, laundry facilities, and patios. Popular attractions Shenandoah Vineyards and Edinburg Mill Museum are ...
10/10 Exceptional! (415 reviews)
"Outstanding Property in Every Possible Way!My husband and I were lucky enough to celebrate our minimoon at Deer Haven and it was exceptional in every way! The pictures don't even do the place justice. The house was spacious, spotless clean, and both decks were incredible. The front deck offered those ..."
Reviewed on Aug 2, 2026
Roadhaven1830
355 Orchard Drive Mount Jackson VA
Stay at this apartment in Mount Jackson. Enjoy free WiFi, 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 Aug 1, 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.
