Winchester Holiday Rentals

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Check prices for these dates

Tonight
14 Jun - 15 Jun
Tomorrow
15 Jun - 16 Jun
Next weekend
20 Jun - 22 Jun
In two weeks
27 Jun - 29 Jun

Holiday Rentals in Winchester

Pet-friendly Greenville Home w/ Private Yard
Interior

Pet-friendly Greenville Home w/ Private Yard

3.0 star property
Pet-friendly Greenville Home w/ Private Yard
Exquisite Hagerstown Home With Deck & Gazebo!
Interior

Exquisite Hagerstown Home With Deck & Gazebo!

3.0 star property
Exquisite Hagerstown Home With Deck & Gazebo!
Quaint Economy Retreat w/ Patio & Spacious Yard!
Interior

Quaint Economy Retreat w/ Patio & Spacious Yard!

3.0 star property
Quaint Economy Retreat w/ Patio & Spacious Yard!
Cozy Richmond Home w/ Fire Pit: Walk, Bike & More!
Interior

Cozy Richmond Home w/ Fire Pit: Walk, Bike & More!

3.0 star property
Cozy Richmond Home w/ Fire Pit: Walk, Bike & More!
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

Are there holiday rentals in Winchester?

Yes, there are holiday rentals close to the most popular sights in Winchester, or you can select a more secluded option if you're looking for a relaxing stay. Winchester is known for its golf courses.

How many holiday rentals are there in Winchester?

Expedia has 3 holiday rentals for your stay in Winchester.

What’s there to see and do in Winchester?

While you're exploring the area, Prairie Creek Reservoir and Campground and YOLO Park are a couple of picturesque spots to get outside and enjoy nature. Winchester Golf Club and Winchester Speedway are other places to visit while you're in town.

What’s a holiday rental in Winchester like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winchester. Holiday rentals offer extras such as patios, hot tubs and fire pits so you'll have all the comforts of home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and busy front desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for family gatherings.