Search Villas in Winchester

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Featured Villas in Winchester and around

Westcott House- Privacy, amenities and space all in one beautiful package!
9.8 out of 10, Exceptional, (86)
"A group of 25 teachers gathered to enjoy professional development and relaxation at the Westcott House. We had a wonderful time relaxing in all of the cozy spots and enjoying the pretty views of the fall leaves. We were glad to see the deck boards replaced from our visit two years ago. Our only complaint this time is how many stubbed toes we went home with from the raised bath mats! The property is wonderful and we hope to return again!"
Westcott House- Privacy, amenities and space all in one beautiful package!
Stunning Former Winery w/ Pool & Mtn Views!
9.4 out of 10, Exceptional, (9)
"This place was perfect for our family and wedding party to all stay together. There was plenty of room, everyone was comfortable, and the scenery was fabulous!"
Stunning Former Winery w/ Pool & Mtn Views!
Private10000sf Retreat GuitarPool Hottub-Wine Area
10.0 out of 10, Exceptional, (19)
"Things were crazy due to a storm that came through right before we arrived but all ended up well and the kids had a blast. Paul always available if/when we needed him"
Private10000sf Retreat GuitarPool Hottub-Wine Area
Historic Virginia Wine Country Villa w/ Pool, Yard
7.6 out of 10, Good, (15)
"The rooms were very engaging. My daughter-in-law was charmed. We had lots of indoor places in which to play. The pool in the backyard was great for adults & children during the warm summer!"
Historic Virginia Wine Country Villa w/ Pool, Yard
Elegant Paris Manor w/ Private Pool!
10.0 out of 10, Exceptional, (1)
"Wonderful property with wonderful people. The Manor house is incredible. The pool and the outdoor space was exactly what we had hoped for. Everyone really enjoyed the wagon ride to the top of the property. Definitely would recommend this family or just a getaway for 2 on a weekend!! John"
Elegant Paris Manor w/ Private Pool!
Amazing Lagoon, Beach, Cross Fit Gym, Fishing
10.0 out of 10, Exceptional, (4)
"This place was like having a resort to ourselves. Very clean and accommodating. The home owner is very personable. From the beautiful quarry, to the swings, floating docks, white beaches and kerokee room this is a true paradise. Come to your next adventure here!"
Amazing Lagoon, Beach, Cross Fit Gym, Fishing
Indulge in Elegance: Four BR Villa with Outdoor Living in Middleburg, VA
2.0 star property
10.0 out of 10, Exceptional, (2)
"Pictures do not do this home justice. We came with 8 moms for a little weekend getaway and couldnt have chosen a better location. The house is beautifully furnished and decorated. The high ceilings and windows let so much light in! The pool and spa are a great addition for anyone looking to hang around the house. Its also a very short walk up the street to get to the Salamander resort for a little spa time. We will definitely be back! "
Indulge in Elegance: Four BR Villa with Outdoor Living in Middleburg, VA
Mid-Long Term Rental villa, pretty location with piano, movie, fitness, trail…
10.0 out of 10, Exceptional, (2)
"Our family of five needed a house near my aging / sick folks and this house was perfect! The owner was very hands on from a communication perspective and my kids loved all the amenities!"
Mid-Long Term Rental villa, pretty location with piano, movie, fitness, trail…
Elegant Paris Manor w/ Private Pool!
3.0 star property
Elegant Paris Manor w/ Private Pool!
Historic Virginia Wine Country Villa w/ Pool, Yard
3.0 star property
Historic Virginia Wine Country Villa w/ Pool, Yard
Stunning Former Winery w/ Pool & Mtn Views!
3.0 star property
Stunning Former Winery w/ Pool & Mtn Views!
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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Other property types in Winchester

Dreamtime - Modern A-frame Cabin w/ Hot tub
10.0 out of 10, Exceptional, (34)
"The cabin was in a beautiful community and setting with a fabulous outdoor area facing the woods. Many amenities in the home that made our stay easy with nicely renovated interior. Owner was very willing and able to offer help with anything and was receptive to feedback. Thank you!"
The price is €359
includes taxes & fees
3 Dec - 4 Dec
Dreamtime - Modern A-frame Cabin w/ Hot tub
Star view cabin-Riverfront
9.8 out of 10, Exceptional, (296)
"The location is perfect, the only criticism we'd have if that the appliances need updated. The kitchen was thin. But the place was very nice, very nice owner and beautiful views. I could definitely see my wife and I going back. "
Star view cabin-Riverfront
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub
10.0 out of 10, Exceptional, (354)
"Deer Haven is a very comfortable and spacious house on a secluded property with a great view from the balcony and upstairs bedroom. It is exactly as described on the VRBO listing. We enjoyed our stay and especially liked sitting around a cozy fire in the outdoor firepit. Would return to Deer Haven again with no hesitation !"
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub
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.

Frequently asked questions

Why book your villa in Winchester with Expedia?
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How can I find cheap villas in Winchester?
Expedia is here to help you look for cheap villas in Winchester. Use our filter tool to select amenities, star rating and budget to refine your search and find the perfect stay in a couple of quick clicks.
What is there to do near my villa in Winchester?
Winchester has enough sights and activities to entertain you for weeks (or months!), starting with Museum of the Shenandoah Valley. Shenandoah Valley Discovery Museum, Bright Box Theatre and Winchester Little Theatre are other wonderful attractions. If you’re staying a while longer, Shenandoah University and Jim Barnett Park are worthwhile additions to your itinerary.