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Featured Villas in Winchester and around

Westcott House- Privacy, amenities and space all in one beautiful package!
Property grounds
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!
Exterior
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
Interior
Private10000sf Retreat GuitarPool Hottub-Wine Area
10.0 out of 10, Exceptional, (20)
"Thank you for making our stay so seamless. We were comfortable and able to have a lot of fun and get a lot accomplished. It’s a great area!"
Private10000sf Retreat GuitarPool Hottub-Wine Area
Historic Virginia Wine Country Villa w/ Pool, Yard
Outdoor dining
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!
Property grounds
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
Miscellaneous
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
Interior
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…
Fridge, microwave, oven, stovetop
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!
Interior
Elegant Paris Manor w/ Private Pool!
3.0 star property
Elegant Paris Manor w/ Private Pool!
Historic Virginia Wine Country Villa w/ Pool, Yard
Outdoor dining
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!
Exterior
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
Outdoor dining
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 €370
includes taxes & fees
3 Dec - 4 Dec
Dreamtime - Modern A-frame Cabin w/ Hot tub
Secluded Pet-Friendly High-Tech Log Cabin in the Woods
Fridge, microwave, oven, stovetop
Secluded Pet-Friendly High-Tech Log Cabin in the Woods
9.6 out of 10, Exceptional, (165)
"I enjoyed every peaceful moment I was there! Living near, and working in a big city is loud and stressful. This was just what the Dr. ordered! Beautiful home in a beautiful setting with great amenities. Loved the lower level deck and propane fire pit that was ready to use! My older dog had a few problems traversing the steps but he loved being there as well!!! Already booked another stay! "
Secluded Pet-Friendly High-Tech Log Cabin in the Woods
Hidden Gem in the woods with hot tub
Property grounds
Hidden Gem in the woods with hot tub
9.4 out of 10, Exceptional, (63)
"Great location, a little out of the way, but very relaxing. Great hot tub and fire pit. My family and I had an amazing time. "
Hidden Gem in the woods with 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?
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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.