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Compare and book 5 Star hotels in Upperville, Virginia

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Check availability on Upperville 5 Star Hotels

Tonight
24 Dec - 25 Dec
Tomorrow
25 Dec - 26 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Upperville 5-star hotels

Exterior
Salamander Resort And Spa

Salamander Resort And Spa

Salamander Resort And Spa
5.0 star property
Middleburg
9.2 out of 10, Wonderful, (373)
"."
Canada
Ivanti
The price is 13.402.479 ₫
16.646.456 ₫ total
includes taxes & fees
7 Jan - 8 Jan 2026
Salamander Resort And Spa
BBQ/picnic Area
Celebration Retreat

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 Upperville.
Lansdowne Resort and Spa

Lansdowne Resort and Spa

44050 Woodridge Pkwy Leesburg VA
The price is 4.477.587 ₫ per night from 1 Jan to 2 Jan
4.477.587 ₫
6.081.329 ₫ total
1 Jan - 2 Jan 2026
includes taxes & fees
8.8/10 Excellent! (1,000 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.

Learn more about Upperville

Hunt country elegance shines at the historic Upperville Horse Show, America's oldest running exhibition where equestrians compete each June. Wander through the quaint village to discover stone buildings, antique shops, and Sky Meadows State Park's hiking trails nearby in Paris.

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Hiking Sky Meadows State Park...
Photo by Michael Gibson
Open Photo by Michael Gibson

Top Upperville Hotel Reviews

Frequently asked questions

What are the best 5-star hotels in Upperville?
Stay in the lap of luxury at Salamander Resort And Spa. This is among the best 5-star hotels in Upperville based on reviews by Expedia customers. From its premium amenities and services to its prime location, you can look forward to the best of everything.
How much does it cost to stay in a 5-star hotel in Upperville?
There are a range of pricing options for a 5-star hotel in Upperville on Expedia. The amount you pay will depend on when you want to travel, length of your trip and other factors. Compare all of the available properties for your desired dates and make use of our pricing and other filters to land the perfect luxury stay.

  • Search for the lowest price per night from 2.834.025 ₫

What makes a hotel 5 stars in Upperville?
Impeccable guest service is integral to every 5-star hotel in Upperville. From the minute you arrive, staff attend to your every need, whether offering luggage assistance and storage or providing in-room massage treatments. Plus, hotels must offer upscale amenities to obtain a 5-star rating. These can include deluxe baths, spas or saunas, swimming pools, gastronomic kitchens and knowledgeable concierge.