Compare Winchester Villas

Featured Villas in Winchester

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

UrbanHaven - 2BD/2.5BA City/Suburb Living

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

Kitchen

Washer

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

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.

Hot Tub

Kitchen

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, barbecue grills, and a water dispenser.

Pool

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

Kitchen

Washer

The Vale at Serà - Modern Retreat w/Sauna

At this cabin, guests have access to a sauna, a hot tub, and laundry facilities. Additional amenities include barbecue grills and a garden.

Hot Tub

Kitchen

The Ridge at Serà - Modern Retreat w/Sauna

At this cabin, guests have access to a sauna, a hot tub, and laundry facilities. Additional amenities include barbecue grills and a garden.

Pool

Hot Tub

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

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

Spark by Hilton Winchester

150 Wingate Dr Winchester VA

$77 nightly

$87 total

May 31 - Jun 1

Total with taxes and fees

9/10 Wonderful! (1,015 reviews)

TRU By Hilton Winchester

118 Mercedes Court Winchester VA

$106 nightly

$115 total

May 24 - May 25

Total with taxes and fees

9/10 Wonderful! (860 reviews)

The George Washington Hotel, A Wyndham Grand Hotel

103 E Piccadilly St Winchester VA

$122 nightly

$138 total

May 25 - May 26

Total with taxes and fees

9.4/10 Exceptional! (1,005 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	13 Villas
Lowest Price	$87
Highest Price	$138
Popular accommodation	Westcott House- Privacy, amenities and space all in one beautiful package!, UrbanHaven - 2BD/2.5BA City/Suburb Living, Private11200sf Retreat GuitarPool Hottub-Wine Area, Chateau Solace: Luxury Glass Villa w/ Hot Tub, Sauna, Gym & 10 Acres, Amazing Lagoon, Beach, Cross Fit Gym, Fishing, Hilltop Villa with exceptional views, game room, starlink, 90 minutes to DC, The Vale at Serà - Modern Retreat w/Sauna, The Ridge at Serà - Modern Retreat w/Sauna, Elegant Paris Manor w/ Private Pool!