Compare Winchester Villas

Featured Villas in Winchester

Country Roads Cottage - Amish Living Reimagined in WV - HOT TUB

$344 nightly

$383 total

Oct 5 - Oct 6

Total with taxes and fees

This villa features a hot tub and barbecue grills. This smoke-free villa also has a garden.

Hot Tub

Kitchen

Guests staying at this villa enjoy a hot tub, an arcade/game room, and barbecue grills.

Hot Tub

Kitchen

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 a garden. This family-friendly villa also has barbecue grills.

Kitchen

Washer

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

Hot Tub

Kitchen

UrbanHaven - 2BD/2.5BA City/Suburb Living

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

Kitchen

Washer

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

Guests of this villa enjoy a hot tub, an arcade/game room, and laundry facilities. Additional amenities include barbecue grills and 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 a water dispenser.

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

Travelodge by Wyndham Winchester

160 Front Royal Pike Winchester VA

$71 nightly

$78 total

Oct 5 - Oct 6

Total with taxes and fees

The George Washington Hotel, A Wyndham Grand Hotel

103 E Piccadilly St Winchester VA

$130 nightly

$148 total

Oct 11 - Oct 12

Total with taxes and fees

La Quinta Inn & Suites by Wyndham Winchester

1055 Millwood Pike, Route 50 East Winchester VA

$103 nightly

$114 total

Oct 4 - Oct 5

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	10 Villas
Lowest Price	$78
Highest Price	$383
Popular accommodation	Country Roads Cottage - Amish Living Reimagined in WV - HOT TUB, Hamatreya- Panoramic Shenandoah Views, 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, Elegant Paris Manor w/ Private Pool!