Explore top 2026 5 Star Hotels in Winchester

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Top Winchester 5 Star hotels

Salamander Resort And Spa

500 North Pendleton Street Middleburg VA

Fully refundableReserve now, pay when you stay

$634 nightly

$723 total

Sep 1 - Sep 2

Total with taxes and fees

A full-service spa, 2 restaurants, and an indoor pool are all featured at this luxury resort. Bring the family and enjoy the children's club, children's pool, ...

9.2/10 Wonderful! (410 reviews)

"The property and staff are amazing. Lots to do if you bring the kiddos, the kids camp let's adults relax and enjoy amenities. The one thing the property can work on is the food menu; more variety is needed. The Red Horse Tavern is a 5-minute walk into town and has the best food!!"

Reviewed on Jul 21, 2026

Celebration Retreat

440 Scenic Overlook Dr Front Royal VA

This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. You'll appreciate the area shuttle, terrace, and garden.

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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.

Winchester Resorts & 5 Star Hotels

Looking for your own little slice of heaven during your next trip? Check out all the best 5-star hotels in Winchester to make sure your trip is as extravagantly comfortable as you expect.

Whether you plan on staying in your room the whole time or getting out and enjoying the city, you’ll be living the life while staying at your luxury accommodation. With so many amenities at your beck and call, you might try to turn your stay into a staycation!

Many of the 5-star hotels have award-winning restaurants you can dine at, as well as plush bedding and a concierge service to take care of your every need. Most also offer pools and modern fitness centers, not to mention high-speed Wi-Fi.

For your next trip, book a hotel that can be your own little hideaway, whether you’re in town for business or leisure. Winchester 5-star hotels provide you with all the comforts and amenities you expect from a sophisticated hotel, with a staff that’s happy to ensure you have everything you need to feel at home.

Whether you’re a first-time guest, or you’ve stayed in 5-star hotels in Winchester before, you’ll have no shortage of options to choose from on your next trip when you book with Travelocity. Browse our vast selection and find great deals on luxury lodging.