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Check prices for these dates

Next weekend
24 Jan - 26 Jan
In two weeks
31 Jan - 2 Feb
In one month
14 Feb - 16 Feb
In two months
14 Mar - 16 Mar

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, (21)
"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, (5)
"This home was spectacular inside and outside! The decor was amazing! This home provided for a wonderful time had by all. Very impressive and well thought out floor plan gave us plenty of room to sit and eat, watch tv, play games and even slip away for a nap! The inside of this home had everything our family needed to enjoy Thanksgiving, just fantastic! The outside was just as special! We took walks with the kids around the quarry - stunning - the fire pit provided for many hours of outside...
Amazing Lagoon, Beach, Cross Fit Gym, Fishing
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

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails

9.8 out of 10, Exceptional, (173)
"I don't even know where to begin. This was exactly the reset my husband and I needed. From the moment we drove up to the cabin and walked inside, we felt so relaxed. We love the outdoors and for a weekend in December, it was quite warm. The breaks in the rain allowed us to walk the trail with our dogs. When the weather was not cooperative, it gave us the chance to curl up inside and watch a movie or play a game. It almost seemed as if the decor was meant for us. Our favorite color is green, we...
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Outdoor dining

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails

9.8 out of 10, Exceptional, (208)
"Highly recommend staying here. We even had a little snow! Family friendly and cozy. "
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
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, (169)
"The cabin was very well appointed. All linens were provided, as well as plenty of spare cleaning products for dishes and laundry. The interior of the cabin was beautiful and well laid out. Unfortunately we had mainly rain while in town, so the technology played a large part for us. The town of Berkely Springs is 20 minutes away and is fantastic! With or without kids along, this is a great place to stay! "
Secluded Pet-Friendly High-Tech Log Cabin in the Woods
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?
We think holiday time shouldn’t be hard, so if you’re on the lookout for villas at a competitive rate, Expedia delivers. Save those pennies and go for an all-inclusive stay, or splurge on a deluxe villa to spoil your loved ones. Use our search filters to find a property in Winchester that matches your needs.
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.