Boutique Hotels in Winchester

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

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check availability on Winchester Boutique Hotels

Top Boutique Hotels in Winchester

Free daily full breakfast
Inn at Evergreen

Inn at Evergreen

3.5 star property
Haymarket
9.4 out of 10, Exceptional, (131)
"Clean,very nice facility "
United States
Matthew P
Inn at Evergreen
TV
Hotel Laurance

Hotel Laurance

3.5 star property
Luray
9.0 out of 10, Wonderful, (159)
"Excellent venue vibrant and historical"
United Kingdom
Rafal
Hotel Laurance
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.
View all properties

Black Friday Sale

Save up to 50% on select hotels
Book now

Top Winchester Hotel Reviews

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent
"The room was perfect. Clean, spacious and the staff was very friendly. Also loved happy hour at the bar, great drinks and appetizers. "
Michelle 1-night trip
Posted 4 days ago
The George Washington Hotel, A Wyndham Grand Hotel
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"Thank you "
Phillip 2-night trip
Posted 5 days ago
La Quinta Inn & Suites by Wyndham Winchester

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 centres, scenic landscape and interesting historical sites. Activities and attractions to experience around Winchester include Bright Box Theater, Museum of the Shenandoah Valley and Old Court House Civil War Museum. You might also like to explore more of the area and take in additional sights like Shenandoah Valley Discovery Museum, Winchester Little Theater and Abram's Delight while you're here.
What kind of weather should I plan for when I travel to Winchester?
Getting an idea of what to expect from the weather in Winchester will help you enjoy your stay to the fullest. The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of 2°C. Average annual precipitation for Winchester is 1172 mm.
What's the best way to get to my boutique hotel in Winchester?
You have a few options for travelling 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, you may want a rental car for your journey.