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Check prices for these dates

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

Featured Villas in Winchester

Westcott House- Privacy, amenities and space all in one beautiful package!
Relax in the hot tub, surrounded by a wooden deck and an outdoor space.

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
Stunning interior with a high ceiling, mezzanine level, and elegant staircase.

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
Relax on the lake's edge, surrounded by lush greenery and tranquil surroundings.

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
Relax under the pergola, surrounded by lush greenery and comfortable seating for four.

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!
Enjoy a serene retreat in this two-story house with a spacious backyard, circular pool, and wooden deck.

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!
Relax in a charming outdoor space with comfortable seating and a flat-screen TV.

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
Relax in the central seating area with a sofa and armchairs, or dine at the small round table with a chair.

Events and Concierge! 6BR Heated Pool Near Wineries

The price is AU$2,352
includes taxes & fees
20 July - 21 July
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
Cozy cabin interior with exposed beams, stone walls, and antique-style furniture, perfect for relaxation and socializing.

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
Enjoy cooking in this well-equipped kitchen with a granite countertop, stainless steel sink, and dishwasher.

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.
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Frequently asked questions

What is there to do near my villa in Winchester?
Whatever your tastes or interests, Winchester has tons of things to keep you entertained. Museum of the Shenandoah Valley, Shenandoah Valley Discovery Museum and Bright Box Theatre are on many visitors' trip plans. Don't forget to check out Winchester Little Theatre, Valerie Hill Winery and Shenandoah University either. With Expedia's hotel deals in Winchester, you'll be able to see more awesome attractions like these with the money you save.