Compare Upperville Villas

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Featured Villas in Upperville

Red Cherry Oasis - Charming 2 bedroom villa with AC, WiFi in serene Aldie

Red Cherry Oasis - Charming 2 bedroom villa with AC, WiFi in serene Aldie

$321 nightly
The price is $366 total per night
$366 total
Oct 7 - Oct 8
Total with taxes and fees
Guests staying at this vacation home enjoy a water park, a hot tub, and laundry facilities. This smoke-free vacation home also has a garden.
Private10000sf Retreat GuitarPool Hottub-Wine Area

Private10000sf Retreat GuitarPool Hottub-Wine Area

At this villa, guests enjoy features like an outdoor pool, a gym, and free WiFi in public areas. Other amenities at this family-friendly villa include a hot tub, an arcade/game room, and a library.
Pool
Hot Tub
Events and Concierge! 6BR Heated Pool Near Wineries

Events and Concierge! 6BR Heated Pool Near Wineries

Guests staying at this villa have access to laundry facilities, a garden, and barbecue grills.
Pool
Kitchen
Highmeadows Estate in the heart of Bluemont Virginia

Highmeadows Estate in the heart of Bluemont Virginia

At this villa, guests have access to a garden.
Kitchen
Pet friendly
Historic Virginia Wine Country Villa w/ Pool, Yard

Historic Virginia Wine Country Villa w/ Pool, Yard

3 out of 5
5024 Leeds Manor Road, Linden, VA
Guests staying at this villa enjoy an outdoor pool, free WiFi in public areas, and barbecue grills. If you drive, put free parking to good use. This smoke-free villa also has a garden.
Pool
Kitchen
Elegant Paris Manor w/ Private Pool!

Elegant Paris Manor w/ Private Pool!

3 out of 5
Guests staying at this villa enjoy an outdoor pool, free WiFi in public areas, and a garden. If you drive, take advantage of free parking. This smoke-free villa also has barbecue grills.
Pool
Kitchen
Stunning Former Winery w/ Pool & Mtn Views!

Stunning Former Winery w/ Pool & Mtn Views!

3 out of 5
An outdoor pool and free WiFi in public areas are features at this villa. There's free parking if you drive.
Pool
Kitchen
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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.

Hotel Options in Upperville

    Lansdowne Resort and Spa

    Lansdowne Resort and Spa

    44050 Woodridge Pkwy, Leesburg, VA
    $282 nightly
    The price is $321 total per night from Oct 13 to Oct 14
    $321 total
    Oct 13 - Oct 14
    Total with taxes and fees
    8.8/10 Excellent! (1,000 reviews)
    La Quinta Inn & Suites by Wyndham Winchester

    La Quinta Inn & Suites by Wyndham Winchester

    1055 Millwood Pike, Route 50 East, Winchester, VA
    $108 nightly
    The price is $118 total per night from Nov 2 to Nov 3
    $118 total
    Nov 2 - Nov 3
    Total with taxes and fees
    9.2/10 Wonderful! (2,167 reviews)
    Hilton Garden Inn Dulles North

    Hilton Garden Inn Dulles North

    22400 Flagstaff Plaza, Ashburn, VA
    $114 nightly
    The price is $129 total per night from Oct 26 to Oct 27
    $129 total
    Oct 26 - Oct 27
    Total with taxes and fees
    8.4/10 Very Good! (1,002 reviews)

Luxury Villas

Book luxury villas in Upperville
There are plenty of ways to up your vacation game, but one of the best is by staying in a luxury villa in Upperville. Villas, with their thoughtful layout and elegant décor, let you travel in style. They come in a variety of sizes and offer a great experience, whether you’re traveling on your own or with a group of friends. Orbitz has fantastic deals on villas in Upperville, so book one now. You’ll feel like a million bucks before you even check in.

Spacious luxury villas in Upperville
You won’t have a problem finding your own space in Upperville. If you’re traveling in a group, go for a three-bedroom or larger villa; separate bedrooms can make it that much easier to keep the peace, especially when you’re all staying in one house. You can also explore Upperville on your own and use a one-bedroom villa as your home base.

A top-end villa experience in Upperville rivals that of a luxury resort. Float in a swimming pool with an elaborate mosaic bottom, work out in your own gym, and let the daily housekeeping staff clean up after you while a private chef whips up one delicious meal after another. This is the life!

Upperville Villas essential information

Accommodation
7 Villas
Lowest Price
$118
Highest Price
$366
Popular accommodation
Red Cherry Oasis - Charming 2 bedroom villa with AC, WiFi in serene Aldie, Private10000sf Retreat GuitarPool Hottub-Wine Area, Events and Concierge! 6BR Heated Pool Near Wineries, Highmeadows Estate in the heart of Bluemont Virginia, Historic Virginia Wine Country Villa w/ Pool, Yard, Elegant Paris Manor w/ Private Pool!, Stunning Former Winery w/ Pool & Mtn Views!