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 $98 per night from Dec 1 to Dec 2
CA $98
CA $108 total
Dec 1 - Dec 2
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 ...
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
The price is CA $115 per night from Nov 8 to Nov 9
CA $115
CA $128 total
Nov 8 - Nov 9
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 ...
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
The price is CA $145 per night from Nov 8 to Nov 9
CA $145
CA $161 total
Nov 8 - Nov 9
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! (2,262 reviews)
"We only spent one night but we loved the location close to some shops, the beds were comfortable and the staff were helpful! I would recommend."
Reviewed on Nov 5, 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 ...
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! (78 reviews)
"This was a quick get away for us and we enjoyed the area and our stay. Everything was as expected, host very responsive and attentive to our needs. Happy we made the trip."
Reviewed on Oct 21, 2026
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
Rileyville VA
Stay at this cabin in Rileyville. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Chalybeate Spring and Fort Valley Public Library are located ...
9.8/10 Exceptional! (345 reviews)
"Beautiful cabin in a private location with a good view. Firewood was provided and grill too. Hot tub was easy and relaxing. Had a great time."
Reviewed on Nov 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.
Things to do
Shenandoah Tour: Self-Guided Drive
CA $24
per traveller
98% of travellers recommend
Sunday Funday Loudoun 2 Winery Tour from DC Metro or Leesburg
CA $141
per adult
