Compare Winchester Villas

Featured Villas in Winchester

Hilltop Villa with exceptional views, game room, starlink, 90 minutes to DC

At this villa, guests have access to an arcade/game room, laundry facilities, and barbecue grills. This family-friendly villa also has a garden.

Chateau Solace: Luxury Glass Villa w/ Hot Tub, Sauna, Gym & 10 Acres

Guests staying at this villa enjoy a gym, a sauna, and a hot tub. Additional amenities include laundry facilities, barbecue grills, and a water dispenser.

UrbanHaven - 2BD/2.5BA City/Suburb Living

At this villa, guests have access to features like laundry facilities.

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

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

Private11200sf 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.

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 water dispenser, and barbecue grills.

Historic Virginia Wine Country Villa w/ Pool, Yard

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.

Stunning Former Winery w/ Pool & Mtn Views!

An outdoor pool and free WiFi in public areas are features at this villa. There's free parking if you drive.

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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

Spark by Hilton Winchester

150 Wingate Dr Winchester VA

$78 nightly

$88 total

Sep 2 - Sep 3

Total with taxes and fees

9.2/10 Wonderful! (1,008 reviews)

Holiday Inn Winchester Se-Historic Gateway by IHG

333 Front Royal Pike Winchester VA

$96 nightly

$107 total

Aug 23 - Aug 24

Total with taxes and fees

9/10 Wonderful! (1,009 reviews)

The George Washington Hotel, A Wyndham Grand Hotel

103 E Piccadilly St Winchester VA

$122 nightly

$138 total

Aug 23 - Aug 24

Total with taxes and fees

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	9 Villas
Lowest Price	$88
Highest Price	$138
Popular accommodation	Hilltop Villa with exceptional views, game room, starlink, 90 minutes to DC, Chateau Solace: Luxury Glass Villa w/ Hot Tub, Sauna, Gym & 10 Acres, UrbanHaven - 2BD/2.5BA City/Suburb Living, Westcott House- Privacy, amenities and space all in one beautiful package!, Private11200sf Retreat GuitarPool Hottub-Wine Area, Amazing Lagoon, Beach, Cross Fit Gym, Fishing, Historic Virginia Wine Country Villa w/ Pool, Yard, Stunning Former Winery w/ Pool & Mtn Views!