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

The Inn At Little Washington
5 out of 5
Middle And Main Streets, Washington, VA
Free cancellationReserve now, pay when you stay
per night
Jan 29 - Jan 30
4.9/5Exceptional! (49 reviews)

"One of the most incredible staffs there is. Everything is thought out for your convenience. Truly pampering. I wouldn’t change a thing."…"

Reviewed on 10 Dec 2019

The Inn At Little Washington
Salamander Resort And Spa
5 out of 5
500 North Pendleton Street, Middleburg, VA
Free cancellationReserve now, pay when you stay
per night
Jan 27 - Jan 28
4.6/5Wonderful! (152 reviews)

"Nice property. Great wine selection. Unsatisfactory food options. Largely unhealthy."…"

Reviewed on 21 Jan 2020

Salamander Resort And Spa
Celebration Retreat
5 out of 5
440 Scenic Overlook Dr, Front Royal, VA
Get Rates
No reviews
Celebration Retreat
Can't see what you're looking for?
See all available properties in Winchester
View all properties
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 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

Recently booked Winchester hotels