Search Villas in Winchester

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Compare 10 Villas in Winchester with updated reviews, rates, and availability.

Private10000sf Retreat GuitarPool Hottub-Wine Area

10.0 out of 10, Exceptional, (22)
"We’ve been twice and hope to return again, the perfect place for a family reunion."
Private10000sf Retreat GuitarPool Hottub-Wine Area

Amazing Lagoon, Beach, Cross Fit Gym, Fishing

10.0 out of 10, Exceptional, (6)
"Fantastic property; owner was very helpful and friendly!"
Amazing Lagoon, Beach, Cross Fit Gym, Fishing

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!

Westcott House- Privacy, amenities and space all in one beautiful package!

9.8 out of 10, Exceptional, (88)
"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!

Historic Virginia Wine Country Villa w/ Pool, Yard

7.6 out of 10, Good, (15)
"We had a great family vacation, everyone lived the pool!!"
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!

Elegant Paris Manor w/ Private Pool!

3.0 star property
Elegant Paris Manor w/ Private Pool!

Stunning Former Winery w/ Pool & Mtn Views!

3.0 star property
Stunning Former Winery w/ Pool & Mtn Views!

Historic Virginia Wine Country Villa w/ Pool, Yard

3.0 star property
Historic Virginia Wine Country Villa w/ Pool, Yard

Private Indoor W/ Pool-WiFi-Aracde-Fire Pit-Mountain Views

Private Indoor W/ Pool-WiFi-Aracde-Fire Pit-Mountain 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.
Don't see what you're looking for?
See all available properties in Winchester
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Winchester

Star view cabin-Riverfront

9.8 out of 10, Exceptional, (312)
"very cute little place, would definitely stay again"
Star view cabin-Riverfront

Dreamtime - Modern A-frame Cabin w/ Hot tub

10.0 out of 10, Exceptional, (37)
"Great cabin. Clean and so welcoming"
The price is SAR 1,084
SAR 1,361 total
includes taxes & fees
30 Apr - 1 May
Dreamtime - Modern A-frame Cabin w/ Hot tub

Riverside cottage, minutes from historic Harpers Ferry! Private river access!

9.8 out of 10, Exceptional, (97)
"This was a perfect clean comfortable place to stay while exploring the Harper's Ferry area. Hosts Scott and Margie are friendly and welcoming"
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
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?
With Expedia, it’s easy to find your ideal villa in Winchester. Vacationing with the family? Take advantage of our filters to look for stays with amenities like a pool. If you’re sticking to a budget, click on how much you want to spend and your preferred star rating. We’ll help you find the right stay that gels with your taste and style.
How can I find cheap villas in Winchester?
With Expedia’s filter tool, comparing cheap villas in Winchester has never been easier. To find properties that give you the most bang for your buck, narrow your search by budget, star rating and amenities.