Find 5 Star Hotels in Winchester, VA from $125

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Our top choices for Winchester 5-star hotels

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Salamander Resort And Spa

Salamander Resort And Spa
5.0 star property
Middleburg
9.2 out of 10, Wonderful, (384 reviews)
"Room was awesome, amazing experiences at the resort and really great customer service"
United States
Anwar
$618 nightly
The price is $705
Apr 5 - Apr 6
Total with taxes and fees
Salamander Resort And Spa
BBQ/picnic area

Celebration Retreat

Celebration Retreat
5.0 star property
Front Royal
Celebration Retreat
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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 Mar 31 to Apr 1
$257 total
Mar 31 - Apr 1
Total with taxes and fees
8.8/10 Excellent! (1,003 reviews)
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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 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.

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Top Winchester Hotel Reviews

Salamander Resort And Spa

Salamander Resort And Spa

6/10 Okay
"For over a decade, staying at Salamander Middleburg was on my bucket list. As a young professional, I always heard raving reviews but felt priced out. So when a friend and I finally secured a Presidents Day weekend stay around $600 per night, we were excited for a true luxury experience. Unfortunately, the value simply was not there. One of the biggest surprises was how little is actually included for guests. Spa treatments cost $195–$365, and even then you only get two hours of access to amenities afterward — with no guest discounts or privileges. Most other activities on property are similarly expensive, leaving very little to do unless you spend hundreds more. We ended up leaving the resort to go to a nearby spa, where we enjoyed full services and lunch for under $120. The arrival experience was even more disappointing. We drove in during the rain to no greeting, no valet, no help with luggage, and no clear signage for check-in. At the desk, we waited without acknowledgment while the lone staff member worked on other tasks. When we were finally assisted, our room wasn’t ready, resulting in a one-hour wait with no apology or offer of refreshments. The room itself was comfortable but unremarkable. To their credit, customer service later apologized and offered breakfast, wine and late check out. Still, for $600+ per night, the service and overall experience did not match the luxury reputation."
Circe 2-night trip
Posted 3 weeks ago
Salamander Resort And Spa

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 $125

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.

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