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
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

Villas in Winchester

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, (89)
"This was just what we needed. We had a family of 30. Included were teens that enjoyed having a separate space and pool table. The upstairs main room was so spacious and the tables were set up like a restaurant. Perfect for meals and mingling. The kitchen was well stocked for cooking meals. We would stay here again. "
Westcott House- Privacy, amenities and space all in one beautiful package!
Private10000sf Retreat GuitarPool Hottub-Wine Area
Interior

Private10000sf Retreat GuitarPool Hottub-Wine Area

10.0 out of 10, Exceptional, (23)
"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
Property grounds

Amazing Lagoon, Beach, Cross Fit Gym, Fishing

10.0 out of 10, Exceptional, (7)
"Fantastic property; owner was very helpful and friendly!"
Amazing Lagoon, Beach, Cross Fit Gym, Fishing
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)
"We had a great family vacation, everyone lived the pool!!"
Historic Virginia Wine Country Villa w/ Pool, Yard
Stunning Former Winery w/ Pool & Mtn Views!
Exterior

Stunning Former Winery w/ Pool & Mtn Views!

9.6 out of 10, Exceptional, (11)
"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!
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!
Events and Concierge! 6BR Heated Pool Near Wineries
TV, fireplace, DVD player, stereo

Events and Concierge! 6BR Heated Pool Near Wineries

The price is SAR 1,857
SAR 5,692 total
includes taxes & fees
21 Jul - 22 Jul
Events and Concierge! 6BR Heated Pool Near Wineries
Elegant Paris Manor w/ Private Pool!
Villa (6 Bedrooms) | Interior

Elegant Paris Manor w/ Private Pool!

3.0 star property
Elegant Paris Manor w/ Private Pool!
Highmeadows Estate in the heart of Bluemont Virginia
Interior

Highmeadows Estate in the heart of Bluemont Virginia

Highmeadows Estate in the heart of Bluemont Virginia
Historic Virginia Wine Country Villa w/ Pool, Yard
TV, fireplace, DVD player, iPod dock

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!
Villa (Multiple Bedrooms) | Interior

Stunning Former Winery w/ Pool & Mtn Views!

3.0 star property
Stunning Former Winery w/ Pool & Mtn Views!
Private Indoor W/ Pool-WiFi-Aracde-Fire Pit-Mountain Views
Interior

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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

10/10 Excellent
"Amazing front desk staff. Very clean. Close to dining and shopping. "
Kelly 1-night trip
Posted 12 hours ago
Microtel Inn & Suites by Wyndham Winchester

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.