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 Shenandoah Valley Discovery Museum.
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
The price is CA $97 per night from Sep 22 to Sep 23
CA $97
CA $106 total
Sep 22 - Sep 23
includes taxes & fees
Stay at this motel in Winchester. Enjoy free parking, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in ...
8.6/10 Excellent! (1,071 reviews)
"Very nice stay great staff and very clean"
Reviewed on Sep 20, 2026
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
The price is CA $182 per night from Sep 27 to Sep 28
CA $182
CA $207 total
Sep 27 - Sep 28
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 ...
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
The price is CA $158 per night from Sep 23 to Sep 24
CA $158
CA $176 total
Sep 23 - Sep 24
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 breakfast and the helpful ...
9.2/10 Wonderful! (2,277 reviews)
"Property was great other than I booked in advance and placed us on a floor that allows dogs. Room smelled like wet dog. Other than that it was clean. In future I will make sure to request a non pet room"
Reviewed on Sep 20, 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 WiFi, free parking, and a garden. Popular attractions Mt Jackson Thrift & Gift and Meems Bottom Covered Bridge ...
9.6/10 Exceptional! (51 reviews)
"Easy access"
Reviewed on Sep 14, 2026
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
Rileyville VA
Stay at this cabin in Rileyville. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Chalybeate Spring and Fort Valley Public Library are ...
10/10 Exceptional! (376 reviews)
"Perfect quick getaway"
Reviewed on Sep 9, 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 ...
9.8/10 Exceptional! (71 reviews)
"Average at best. 2 out of 4 burners in the stove did not work. Outside grill was grease filled and caught on fire, kitchen is ill-equipped for cooking. If u plan on baking meals…. Bring everything you need! Relaxing experience in the woods but lacked basic upkeep."
Reviewed on Sep 2, 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.
