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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Villas in Winchester and around

Westcott House- Privacy, amenities and space all in one beautiful package!
Enjoy a covered outdoor space with a staircase and seating area.

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

9.8 out of 10, Exceptional, (90)
"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
Relax by the pool surrounded by lounge chairs and a clear water feature.

Private10000sf Retreat GuitarPool Hottub-Wine Area

10.0 out of 10, Exceptional, (26)
"We’ve been twice and hope to return again, the perfect place for a family reunion."
Private10000sf Retreat GuitarPool Hottub-Wine Area
Events and Concierge! 6BR Heated Pool Near Wineries
Surrounded by lush greenery and rolling hills, this estate offers a serene natural setting with multiple buildings amidst manicured lawns and trees.

Events and Concierge! 6BR Heated Pool Near Wineries

The price is €1,241
includes taxes & fees
14 Aug - 15 Aug
Events and Concierge! 6BR Heated Pool Near Wineries
Amazing Lagoon, Beach, Cross Fit Gym, Fishing
Relax in a serene outdoor oasis with a view of the water and lush surroundings.

Amazing Lagoon, Beach, Cross Fit Gym, Fishing

10.0 out of 10, Exceptional, (9)
"Great home on such lovely, large private property. Everything was beautifully decorated and so well thought out. Comfortable beds, well-stocked kitchen, and amazing view from all the rooms. The kids especially loved peddle boating, and walking around the quarry to find hidden treasures. There were just so many things to do! We highly recommend this place, and hope to come back soon."
Amazing Lagoon, Beach, Cross Fit Gym, Fishing
Historic Virginia Wine Country Villa w/ Pool, Yard
Escape to a tranquil rural retreat surrounded by lush greenery and rolling hills.

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
Highmeadows Estate in the heart of Bluemont Virginia
Terrace/patio

Highmeadows Estate in the heart of Bluemont Virginia

Highmeadows Estate in the heart of Bluemont Virginia
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!
Historic Virginia Wine Country Villa w/ Pool, Yard
Escape to a serene rural landscape surrounded by lush greenery and rolling hills, featuring traditional houses with gabled roofs.

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!
Red Cherry Oasis - Charming 2 bedroom villa with AC, WiFi in serene Aldie
Exterior

Red Cherry Oasis - Charming 2 bedroom villa with AC, WiFi in serene Aldie

The price is €256
includes taxes & fees
2 Sept - 3 Sept
Red Cherry Oasis - Charming 2 bedroom villa with AC, WiFi in serene Aldie
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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Top Winchester Hotel Reviews

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

10/10 Excellent
"I’ve stayed here before with my two dogs, this time without…..Rooms are very spacious and clean, Staff at desk always friendly and helpful. Breakfast good with friendly staff….Convenient off/on from Highway."
Laura 1-night trip
Posted 1 day ago
Comfort Inn & Suites Winchester

Frequently asked questions

Why book your villa in Winchester with Expedia?
With Expedia, it's easy to find your ideal villa in Winchester. Holidaying 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.
What is there to do near my villa in Winchester?
Whatever you love doing, Winchester has plenty of things to keep you on the move. Rock Harbour Golf Course, The Kernstown Battlefield and Museum of the Shenandoah Valley are on many visitors' lists. Don't head home without exploring Apple Blossom Mall, Jim Barnett Park and Handley Regional Library either. With Expedia's Winchester hotel deals, you'll be able to discover even more renowned attractions like these with the money you save.