Winchester, VA

Travel Guide

Winchester
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby

Where to stay in Winchester

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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.

Old Town Winchester
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Winchester Historic District

While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Winchester Little Theater.

Winchester Historic District
Red Roof Inn Winchester, VA

Red Roof Inn Winchester, VA

2 out of 5
991 Millwood Pike, Winchester, VA
The price is ₩98,033 per night from Nov 2 to Nov 3
₩98,033
₩106,660 total
Nov 2 - Nov 3
includes taxes & fees
Stay at this hotel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the clean rooms in our reviews. Popular attractions ...
7.4/10 Good! (1,005 reviews)
Good Stay
Good stay for an overnight trip. Kumar treated us like very special people! Clean and very comfortable. Only problem - ADA shower very difficult to use for someone less then 5’4. Reaching the shower head was impossible. Would not recommend this place for special needs.

Reviewed on Oct 22, 2025

Red Roof Inn Winchester, VA
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

3 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
The price is ₩145,792 per night from Nov 2 to Nov 3
₩145,792
₩158,621 total
Nov 2 - Nov 3
includes taxes & fees
Stay at this 3-star 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! (2,190 reviews)
Amazing

Reviewed on Oct 27, 2025

La Quinta Inn & Suites by Wyndham Winchester
Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

2.5 out of 5
195 Kernstown Commons Blvd, Winchester, VA
The price is ₩143,731 per night from Nov 1 to Nov 2
₩143,731
₩156,380 total
Nov 1 - Nov 2
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 ...
9.4/10 Exceptional! (1,045 reviews)
Front desk manager Roy was very nice. Tried his best to accommodate us. I didn’t realize this was a pet friendly place when I booked the rooms. Dogs were everywhere, and some could be heard barking. Plus I’m allergic! But the roomed were clean. Dogs quieted down and the stay was good. Roy was a good ...

Reviewed on Oct 26, 2025

Comfort Inn & Suites Winchester
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.
Canal Cabins

Canal Cabins

3 out of 5
143 Louie's Ln, Paw Paw, WV
Stay at this 3-star cabin in Paw Paw. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Paw Paw Tunnel and Chesapeake and Ohio Canal ...
9.6/10 Exceptional! (11 reviews)
Great place for bikers to stay

Reviewed on Oct 25, 2025

Canal Cabins
Road Haven 1830

Road Haven 1830

3 out of 5
355 Orchard Drive, Mount Jackson, VA
Stay at this 3-star apartment in Mount Jackson. Enjoy free parking and a garden. Popular attractions Mt Jackson Thrift & Gift and Meems Bottom Covered Bridge ...
9.4/10 Exceptional! (37 reviews)
This cottage was super clean and cozy!!! The back yard was so relaxing with many games to keep adults and young kids entertained . I would highly recommend this place. I would live to stay again. The owner was very sweet also ❤️

Reviewed on Oct 15, 2025

Road Haven 1830
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.

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