This site uses cookies for analytics, personalization, and advertising. By continuing to browse the site, you agree to our use of cookies. Learn More
trover photo by Fernando Begay
Compare and book 5 Star hotels in Winchester, Virginia
Search over 1 million properties and 550 airlines worldwide
Search over 1 million flights, hotels, packages, and more
No Expedia cancellation fee to change or cancel almost any hotel reservation
Top Winchester 5 Star Hotels
Middle And Main Streets, Washington, VA
Free cancellationReserve now, pay when you stay
per night
Jan 29 - Jan 30
4.9/5Exceptional! (49 reviews)
Reviewed on 10 Dec 2019
500 North Pendleton Street, Middleburg, VA
Free cancellationReserve now, pay when you stay
per night
Jan 27 - Jan 28
4.6/5Wonderful! (152 reviews)
Reviewed on 21 Jan 2020
Can't see what you're looking for?
See all available properties in 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.
Pocket Guide: 5 Star Hotels in Winchester
Search for hotels in Winchester on Expedia.co.uk. You can easily find your hotels in Winchester using one of the methods below:
- View our selection of featured hotels in Winchester
- Use the map to find hotels in the Winchester neighborhood you prefer
- Use the filters to see hotels in a specific area of Winchester, select a specific theme, brand, or hotel class from basic (1 Star) to luxury hotels (5 Stars) in Winchester
- Enter your travel dates to view the best deals on hotels in Winchester - while they last
More trip options
- Hotels Near Winchester, Virginia
- Accommodation near Winchester Attractions
- More accommodation types in Winchester
- Choose Your Winchester Hotel Style
- Hotels in Winchester by Star Rating
- Recommended cities for you
- Expedia Latest Trends
- Ashburn Hotels (60.45 km)
- Sterling Hotels (66.79 km)
- Middleburg Hotels (42.82 km)
- Leesburg Hotels (52.21 km)
- Charles Town Hotels (28.8 km)
- Chantilly Hotels (67.12 km)
- Harpers Ferry Hotels (40.52 km)
- Warrenton Hotels (61.39 km)
- Front Royal Hotels (29.01 km)
- Blue Ridge Mountains Hotels (384.95 km)
- Culpeper Hotels (83.57 km)
- Northern Virginia Hotels (57.91 km)
- Shenandoah National Park Hotels (80.49 km)
- Washington Hotels (50.94 km)
- Gainesville Hotels (63.23 km)
- Berkeley Springs Hotels (49.7 km)
- Shepherdstown Hotels (41.63 km)
- Woodstock Hotels (45.24 km)
- Appalachian Mountains Hotels (112.3 km)
- Strasburg Hotels (27.47 km)
- Winchester Medical Center
- Shenandoah University
- Bluemont Vineyard
- Front Royal Entrance Shenandoah National Park
- Dinosaur Land
- Skyline Caverns
- Apple Blossom Mall
- Shenandoah Valley Discovery Museum
- Museum of the Shenandoah Valley
- Winchester Little Theater
- Patsy Cline Historic House
- Rock Harbor Golf Course
- Mackintosh Fruit Farm
- Holy Cross Abbey
- Wilson's Wild Animal Park
- Jim Barnett Park
- Wayside Theater
- Handley Regional Library
- Stonewall Jackson's Headquarters
- George Washington's Office
- Business Hotels (35)
- Cheap Hotels (27)
- Family-Friendly Hotels (36)
- Golf Hotels (34)
- Historic Hotels (40)
- Hotels Suites (6)
- Hotels near Museums (34)
- Hotels with Air Conditioning (44)
- Hotels with Balcony (6)
- Hotels with Breakfast (37)
- Hotels with Connecting Rooms (19)
- Hotels with Entertainment (12)
- Hotels with Gym (23)
- Hotels with Hot Tubs & Jacuzzis (14)
- Hotels with Laundry Service (28)
- Hotels with Parking (41)
- Hotels with Parking (38)
- Hotels with Pool (27)
- Hotels with Restaurant (38)
- Hotels with Room Service (6)
- Hotels with Wifi (41)
- Hotels with a Bar (23)
- Hotels with a View (11)
- Luxury Hotels (19)
- Mountain Hotels (8)
- Pet-Friendly Hotels (23)
- Romantic Hotels (14)
- Shopping Hotels (28)
- Spa Hotels (11)
- Sports Hotels (26)
- Wedding Hotels (19)
- Winery Hotels (15)
- Las Vegas Hotels
- New York Hotels
- Orlando Hotels
- Los Angeles Hotels
- Miami Hotels
- San Francisco Hotels
- New Orleans Hotels
- Chicago Hotels
- Fort Lauderdale Hotels
- Boston Hotels
- Honolulu Hotels
- San Diego Hotels
- Washington Hotels
- Toronto Hotels
- Anaheim Hotels
- Atlanta Hotels
- Nashville Hotels
- Seattle Hotels
- Phoenix Hotels
- Myrtle Beach Hotels
Hotels
Recently booked Winchester hotels
4 out of 5
A verified traveller stayed at Travelodge by Wyndham Winchester
Posted 13 days ago
5 out of 5
A verified traveller from North Babylon, N.Y. stayed at Hotel Strasburg
Posted 2 months ago
5 out of 5
A verified traveller from Boone, NC stayed at Hampton Inn Winchester-University/Mall Area
Posted 2 months ago
5 out of 5
A verified traveller stayed at TownePlace Suites by Marriott Winchester
Posted 6 months ago
062e40d8-67ed-4334-b301-7616843a23ef8c3b0341-be81-4b0d-aa8a-57ea0203c3ef062e40d8-67ed-4334-b301-7616843a23ef4be93cec-29ff-4e3f-8c0e-dccc106653f4