Compare Winchester Villas

Featured Villas in Winchester

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

$317 nightly

$362 total

Feb 16 - Feb 17

Total with taxes and fees

Guests staying at this villa enjoy a hot tub, laundry facilities, and a garden.

Hot Tub

Kitchen

Westcott House- Privacy, amenities and space all in one beautiful package!

Guests staying at this villa enjoy a hot tub, laundry facilities, and barbecue grills. This smoke-free villa also has a garden.

Hot Tub

Kitchen

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

Amazing Lagoon, Beach, Cross Fit Gym, Fishing

At this villa, guests enjoy features like an outdoor pool, a gym, and a sauna. Other amenities at this beach villa include laundry facilities, a garden, and barbecue grills.

Pool

Kitchen

The Vale at Será - Brand New Modern WV Retreat

Wardensville WV

At this villa, guests have access to a sauna, a hot tub, and laundry facilities. This villa also has barbecue grills.

Pool

Hot Tub

Highmeadows Estate in the heart of Bluemont Virginia

This villa is a smoke-free villa.

Mountain view

Pet friendly

The Ridge at Será - Brand New Modern WV Retreat

Wardensville WV

At this villa, guests have access to a sauna, a hot tub, and laundry facilities. This villa also has barbecue grills.

Pool

Hot Tub

Guests staying at this villa enjoy an outdoor pool, free WiFi in public areas, and a garden. If you drive, put free parking to good use. This smoke-free villa also has barbecue grills.

Pool

Kitchen

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

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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 Winchester

La Quinta Inn & Suites by Wyndham Winchester

1055 Millwood Pike, Route 50 East Winchester VA

$100 nightly

$109 total

Feb 16 - Feb 17

Total with taxes and fees

9.2/10 Wonderful! (2,264 reviews)

The George Washington Hotel, A Wyndham Grand Hotel

103 E Piccadilly St Winchester VA

$122 nightly

$138 total

Feb 22 - Feb 23

Total with taxes and fees

9.2/10 Wonderful! (1,000 reviews)

Microtel Inn & Suites by Wyndham Winchester

150 Faraday Plaza Winchester VA

$86 nightly

$93 total

Feb 22 - Feb 23

Total with taxes and fees

9/10 Wonderful! (1,446 reviews)

Luxury Villas

Book luxury villas in Winchester
There are plenty of ways to up your vacation game, but one of the best is by staying in a luxury villa in Winchester. 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 Winchester, so book one now. You’ll feel like a million bucks before you even check in.

Spacious luxury villas in Winchester
You won’t have a problem finding your own space in Winchester. 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 Winchester on your own and use a one-bedroom villa as your home base.

A top-end villa experience in Winchester 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!

Winchester Villas essential information

Accommodation	11 Villas
Lowest Price	$93
Highest Price	$362
Popular accommodation	Red Cherry Oasis - Charming 2 bedroom villa with AC, WiFi in serene Aldie, Westcott House- Privacy, amenities and space all in one beautiful package!, Private10000sf Retreat GuitarPool Hottub-Wine Area, Amazing Lagoon, Beach, Cross Fit Gym, Fishing, The Vale at Será - Brand New Modern WV Retreat, Highmeadows Estate in the heart of Bluemont Virginia, The Ridge at Será - Brand New Modern WV Retreat, Historic Virginia Wine Country Villa w/ Pool, Yard, Elegant Paris Manor w/ Private Pool!