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Featured Villas in Winchester

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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.

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Winchester Villa Rentals

Wake up, stretch, and pad across the bedroom to your kitchen. You’ve got a busy day of exploring ahead, and you’ll face it best with a mug of piping hot coffee in your hand. Look out the window at the rising sun and take a deep breath.

This can be your life if you rent a villa in Winchester. Once upon a time, villas were huge Roman buildings owned by the wealthiest citizens. These days, you can still find palatial villas—but there’s smaller, cozier options to choose from as well.

What makes villas so special? First, they offer you and your travel group privacy and space. After a long day of exploring Winchester, a villa truly becomes your home away from home. Lay down in one of the bedrooms for a midday catnap, then make use of the fully stocked kitchen and craft a culinary masterpiece to serve up on the private patio. Your companions will be talking about it for years to come.

Do you want to really treat yourself during your time in Winchester? Go for it. Luxury villas will make you feel like a million bucks as you sip champagne on a balcony, or cozy up with your someone special and take in the classy artwork. Put that big marble tub to good use. The more fragrant bath salts, the merrier!

At Travelocity, we offer the vacation villa options you want, with a number of villas available for rent in Winchester. Get the most out of your time in this fascinating city, wise wanderer, and browse our available villas today.

Winchester Villas essential information

Accommodation
12 Villas
Lowest Price
CA $84
Highest Price
CA $177
Popular accommodation
Westcott House- Privacy, amenities and space all in one beautiful package!, Stunning Former Winery w/ Pool & Mtn Views!, Private10000sf Retreat GuitarPool Hottub-Wine Area, Historic Virginia Wine Country Villa w/ Pool, Yard, Elegant Paris Manor w/ Private Pool!, Amazing Lagoon, Beach, Cross Fit Gym, Fishing, Indulge in Elegance: Four BR Villa with Outdoor Living in Middleburg, VA, Mid-Long Term Rental villa, pretty location with piano, movie, fitness, trail…, Elegant Paris Manor w/ Private Pool!, Historic Virginia Wine Country Villa w/ Pool, Yard, Stunning Former Winery w/ Pool & Mtn Views!