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.

Eid al-Fitr Sale

Members save up to 40% on hotels. Plan this year’s big trip and save.

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
The price is SAR 368 per night from Mar 8 to Mar 9
SAR 368
SAR 400 total
8 Mar - 9 Mar
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! (2,264 reviews)
Staff was very courteous and friendly throught our entire stay! Everything was updated and very clean. Kids LOVED the pool and breakfast.

Reviewed on 10 February 2026

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

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike Winchester VA
The price is SAR 263 per night from Feb 15 to Feb 16
SAR 263
SAR 286 total
15 Feb - 16 Feb
includes taxes & 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. ...
8.6/10 Excellent! (1,083 reviews)
Room was good for the price, staff was friendly and helpful

Reviewed on 4 February 2026

Travelodge by Wyndham Winchester
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

3.5 out of 5
103 E Piccadilly St Winchester VA
The price is SAR 458 per night from Feb 19 to Feb 20
SAR 458
SAR 519 total
19 Feb - 20 Feb
includes taxes & fees
Book a stay at this spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
9.4/10 Exceptional! (1,004 reviews)
Clean nice room Great location for restaurants

Reviewed on 28 January 2026

The George Washington Hotel, A Wyndham Grand Hotel
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.
Star view cabin-Riverfront

Star view cabin-Riverfront

Rileyville VA
Stay at this cabin in Rileyville. Enjoy laundry facilities, tennis courts, and patios. Our guests praise the property condition in our reviews. Popular attractions ...
9.8/10 Exceptional! (345 reviews)
The host was exceptional and quick to respond to questions. Loved the cabin, it was in great condition, clean and very nicely set up. The views to the river and the mountains beyond were breath taking with the snow and ice from a recent storm.

Reviewed on 5 February 2026

Star view cabin-Riverfront
Falling Leaf Cabin - Rustic Charm With Modern Decor!

Falling Leaf Cabin - Rustic Charm With Modern Decor!

Rileyville VA
Book a stay at this family-friendly cabin in Rileyville. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Chalybeate Spring and Fort Valley ...
9.8/10 Exceptional! (307 reviews)
Cabin was as described and easy access with great communication with the host.

Reviewed on 18 January 2026

Falling Leaf Cabin - Rustic Charm With Modern Decor!
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 ...
10/10 Exceptional! (57 reviews)
The house was beautiful and well taken care of. We had everything we needed to just hold up cozy in the house. The hot tub was a great ammenity.

Reviewed on 23 January 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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