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 Winchester Little Theater.
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
The price is CA $123 per night from Jul 26 to Jul 27
CA $123
CA $139 total
Jul 26 - Jul 27
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 ...
9/10 Wonderful! (1,010 reviews)
"This newly renovated, squeaky clean hotel is a favorite of ours as a stop off on our I-81 journeys. It is at an excellent location, quiet, clean, and the rooms are spacious. Hotel gym, breakfast, and pool are excellent additions to our stay here. They are also pet friendly and have a nice spot to ..."
Reviewed on Jun 28, 2026
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
The price is CA $139 per night from Jul 30 to Jul 31
CA $139
CA $154 total
Jul 30 - Jul 31
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (990 reviews)
"They had free EV charging."
Reviewed on Jun 30, 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
The price is CA $132 per night from Jul 26 to Jul 27
CA $132
CA $148 total
Jul 26 - Jul 27
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 ...
9.2/10 Wonderful! (1,005 reviews)
"Clean. Friendly staff. Zero complaints."
Reviewed on Jun 28, 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! (42 reviews)
"everything was easy / clean / worked and the property is lovely."
Reviewed on Jun 27, 2026
Dreamtime - Modern A-frame Cabin w/ Hot tub
Berkeley Springs WV
Stay at this cabin in Berkeley Springs. Enjoy free WiFi, 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 Jun 8, 2026
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! (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 Jun 15, 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.
