Winchester, VA

Travel Guide

Winchester
Winchester
Handley Library
Gardens at Glen Burnie House.
A nice 3 block outdoor downtown shopping area with dining and bars also.

Where to stay in Winchester

The Courthouse in Winchester, Virginia.

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
Buildings and streets in the historic part of the ancient city of Winchester in Virginia.

Winchester Historic District

While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Shenandoah Valley Discovery Museum.

Winchester Historic District
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
$98 nightly
The price is $107 total per night from Feb 1 to Feb 2
$107 total
Feb 1 - Feb 2
Total with taxes and 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! (2,251 reviews)
Very Friendly staff and clean rooms!

Reviewed on Jan 25, 2026

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

Microtel Inn & Suites by Wyndham Winchester

2.5 out of 5
150 Faraday Plaza Winchester VA
$85 nightly
The price is $92 total per night from Feb 2 to Feb 3
$92 total
Feb 2 - Feb 3
Total with taxes and 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 and the clean ...
9/10 Wonderful! (1,441 reviews)
Perfect for a single night, relatively clean, very friendly staff and decent breakfast.

Reviewed on Jan 18, 2026

Microtel Inn & Suites by Wyndham Winchester
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike Winchester VA
$70 nightly
The price is $76 total per night from Feb 1 to Feb 2
$76 total
Feb 1 - Feb 2
Total with taxes and fees
Stay at this motel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.4/10 Very Good! (1,071 reviews)
Good value, clean, comfortable bed. Bathroom fan was connected to light so couldnt leave light on in the bathroom as a night light. Fan was loud. All in all..id stay there again when traveling.

Reviewed on Jan 20, 2026

Travelodge by Wyndham 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.
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.

Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.

Berkeley Springs WV
Stay at this cabin in Berkeley Springs. Enjoy laundry facilities, patios, and cable/satellite TV service. Popular attractions Cacapon Golf Course and Colonial ...
9.8/10 Exceptional! (282 reviews)
Secluded romantic getaway just as we were looking for.

Reviewed on Jan 12, 2026

Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.
Private, light filled retreat space...
     with your own pickleball court!

Private, light filled retreat space... with your own pickleball court!

Berkeley Springs WV
Stay at this cabin in Berkeley Springs. Enjoy cable/satellite TV service, an in-room coffeemaker, and in-room fireplaces. Popular attractions Ice House and Berkeley ...
10/10 Exceptional! (68 reviews)
What a homey, comfortable and clean mountain retreat that is only 10 minutes from town. You will want to stay here!

Reviewed on Jan 15, 2026

Private, light filled retreat space... with your own pickleball court!
Dreamtime - Modern A-frame Cabin w/ Hot tub

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! (53 reviews)
We absolutely loved the Dreamtime A-frame cabin. The house is simply perfect with a well appointed kitchen, great fireplace, hot tub, and comfortable beds. I could not have asked for more.

Reviewed on Jan 8, 2026

Dreamtime - Modern A-frame Cabin w/ Hot tub
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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