A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.

Compare and book 5 Star hotels in Winchester, Virginia

  • 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 5 Star Hotels

Tonight
24 Oct - 25 Oct
Tomorrow
25 Oct - 26 Oct
Next weekend
30 Oct - 1 Nov
In two weeks
6 Nov - 8 Nov

Our top choices for Winchester 5-star hotels

A large, multi-story building with a symmetrical facade, multiple chimneys, and a central entrance with columns.
A swimming pool with lounge chairs and a sunset view.
A restaurant with round tables, booths, and a chandelier.
A picnic setup with a cheese board, grapes, and a glass of white wine on a wooden table, surrounded by lush greenery and a pergola.

1. Salamander Middleburg

Salamander Middleburg
Middleburg
United States
Mohamed
₹59,897
₹73,214 total
includes taxes & fees
23 Nov - 24 Nov
Salamander Middleburg
Billiards
Front of property
Room
Dining

2. Celebration Retreat

Celebration Retreat
Front Royal
Celebration Retreat
Save an average of 15% on thousands of hotels when you're signed in

Winchester and related destinations

Stroll through the charming pedestrian mall in the historic district, where shops and excellent restaurants await. Delve into local culture at the Museum of the Shenandoah Valley or catch a show at the Bright Box Theatre.

See all hotels in Winchester
A white neoclassical building with columns, an American flag, and a clock tower.

Top Winchester Hotel Reviews

Find out more about Winchester

Stay in Luxury: 5 Star Hotels in Winchester

There's nothing wrong with enjoying the finer things in life. Indulge your every desire on your upcoming leisure time. Treat yourself with a stay in a 5-star hotel during your Winchester trip. You'll join the multitudes of holidaymakers who have made Winchester so fashionable recently. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Don't wait any longer. Reserve one of our 5-star hotels in Winchester and indulge in the finer things in life for a while.

5-Star Hotels in Winchester

You'll have a wonderful time at one of these 5-star hotels. Exceptional customer care, luxurious bedding, and deeply relaxing spa offerings are waiting for you. You're sure to find exactly the accommodation you need. You can also expect excellent customer service from these hotels, so get ready for a wonderful adventure. What kind of amenities will make your stay a wonderful one? 24-hour room service, so you can order that berry tart in the wee hours of the morning? A body scrub that will leave you feeling refreshed and alive? Butler services? Whatever it is your heart desires, you're bound to find it here. Don't want to take our word for it? Explore our listings and pick the perfect accommodation for your needs. 

But you aren't going to spend your entire holiday in your room, of course. You're in luck. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what's on your agenda, the 5-star hotels in Winchester are waiting for you to relax after an exciting day.

Make Your Escape

The results are in, and Winchester 5-star hotels are the place to be when you book your next holiday. If you've been dreaming about a holiday set here, then go ahead and book it. It's time to plan your next great escape -- this is a great time to find 5-star hotel deals in Winchester! Choose one of our Winchester 5-star hotels today and soothe yourself in luxe surroundings at your convenience.

Expedia India is rated 4 stars by Feefo based on 1038 reviews

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Winchester?
You'll find a variety of pricing options for 5-star hotels in Winchester on Expedia. The amount you pay will depend on when you travel, trip length and other factors. Compare all of the available properties for your chosen dates and make use of our pricing and other filters to score the ideal upscale stay.
  • Search for the lowest price per night
What makes a hotel 5 stars in Winchester?
In Winchester, a hotel needs to offer a certain number of upscale features to be rated 5 stars. These can include gourmet restaurants, on-site gyms, saunas and spas, luxury toiletries, premium bedding and more. What also sets 5-star hotels apart is their guest-focused service. You can look forward to things like concierge services, nightly turn-down services and in-room massage. Some may even offer special touches such as welcome gifts.
Are there any 5-star all-inclusive resorts in Winchester?
Our filter tool is the easiest way to narrow down what you're looking for. Check the "All inclusive" and "5-star" boxes to see the most upscale resorts in Winchester where your room, meals, entertainment and activities are included in the upfront price. At these stays, your trip is pure indulgence from the moment you arrive.

Explore a world of travel with Expedia