Find Boutique Hotels in Winchester, VA

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Winchester Boutique Hotels

This weekend
Next weekend

Top Winchester Boutique Hotels

The George Washington Hotel, A Wyndham Grand Hotel

3.5 star property
9.4 out of 10, Exceptional, (1014)
"Perfect location to visit for business or pleasure!"
The price is NT$3,842
NT$4,353 total
includes taxes & fees
Oct 2 - Oct 3
The George Washington Hotel, A Wyndham Grand Hotel

La Quinta Inn & Suites by Wyndham Winchester

3.0 star property
9.2 out of 10, Wonderful, (2167)
"Would stay again if in the area. "
The price is NT$3,281
NT$3,570 total
includes taxes & fees
Sep 29 - Sep 30
La Quinta Inn & Suites 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.

Top Winchester Hotel Reviews

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

What's there to see and do in Winchester?
Visitors speak positively about this destination's major shopping centers, scenic landscape, and interesting historical sites. Activities and attractions to experience around Winchester include Bright Box Theater, Winchester Little Theater, and Museum of the Shenandoah Valley. You might also like to explore more of the area and take in additional sights like Shenandoah Valley Discovery Museum, Abram's Delight, and Wayside Theater while you're here.
What kind of weather should I plan for when I travel to Winchester?
Having a good idea of the weather in Winchester will help you enjoy your stay to the fullest. The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 36°F. Average annual precipitation for Winchester is 46 inches.
What's the best way to get to my boutique hotel in Winchester?
You have a few options for traveling to and around Winchester. The closest major airport is Martinsburg, WV (MRB-Eastern West Virginia Regional), which is located 18 mi (28.9 km) from the heart of the city. If you'd like to explore around the area, consider renting a car to take in more sights.