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

Find 5 Star Hotels in Winchester, VA from $123

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Winchester 5 Star Hotels

Our top choices for Winchester 5-star hotels

A large, two-story house with a central entrance, multiple chimneys, and a well-maintained lawn with a pathway leading to the entrance.

1. Salamander Middleburg

Salamander Middleburg
5.0 star property
Middleburg
9.2 out of 10, Wonderful, (430 reviews)
"This property is amazing"
United States
jonathan
$664 nightly
The price is $756
Dec 15 - Dec 16
Total with taxes and fees
Salamander Middleburg
Dining

2. Celebration Retreat

Celebration Retreat
5.0 star property
Front Royal
Celebration Retreat
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Winchester.
Lansdowne Resort and Spa

Lansdowne Resort and Spa

44050 Woodridge Pkwy Leesburg VA
$225 nightly
The price is $257 total per night from Nov 22 to Nov 23
$257 total
Nov 22 - Nov 23
Total with taxes and fees
Still don't see what you're looking for?
See all properties in Winchester.
You can also use these popular filters to refine your search.
PoolSpaHot tubBreakfast includedWaterpark
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 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 Theater.

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

Indulge yourself on your impending escape. After all, you love the finer things in life, both at home and when you book a getaway. You'll join the multitudes of vacationers who have made Winchester so popular in the last year. There's no reason to delay a getaway to Winchester any longer. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll want for nothing during your getaway. Reserve one of our 5-star hotels in Winchester and indulge in the finer things in life for a while. You deserve an outstanding getaway.

Book the Best Winchester 5-Star Hotels

Don't be afraid to live the high life while you're on vacation, along with pristine rooms. High-end restaurants, concierges, and in-room massages are all at the ready. You're sure to find exactly the accommodation you need. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. How do you want to relax? A concierge to help you pick out your next adventure? A Swedish massage to help your cares fall away? Beautiful furniture, piping hot coffees, and even spectacular views...these hotels have it all.

Can't wait to get outside? We've got you covered. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what you end up doing, the 5-star hotels in Winchester are the perfect place to relax after a busy day. Ready to learn more? Then explore the 395 reviews various guests have left on Expedia and get to know these places.

Your Getaway Starts Today

The results are in, and Winchester 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. It's time to plan your next great escape -- Expedia can help you land a great deal on accommodation. Pick out one of Expedia's Winchester 5-star hotels today and settle down in the lap of luxury when you're ready.

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. How much you'll pay will depend on when you want to travel, length of stay and other factors. Compare available properties for your preferred dates and make use of our pricing and other filters to score the ideal high-end stay.

  • Search for the lowest price per night from $123

What makes a hotel 5 stars in Winchester?
In Winchester, a hotel needs to provide a specific number of high-end conveniences to earn 5 stars. These may include on-site gyms, saunas and spas, gourmet restaurants, luxury toiletries, premium bedding and more. What also sets 5-star hotels apart is their superior service. You can expect things like in-room massages, concierge services and nightly turn-down services. Some may also offer extra touches such as welcome gifts.
Are there any 5-star all-inclusive resorts in Winchester?
Find a luxurious escape that includes your room, meals, drinks and entertainment in Winchester with the help of our filters. Search for resorts rated 5 stars and select the "All inclusive" filter. Have a look at what's included in the upfront price. That way, you can take full advantage of all the perks on offer when you get there.

Explore a world of travel with Expedia