Search Holiday Rentals in Winchester

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Check prices for these dates

Tonight
17 Jul - 18 Jul
Tomorrow
18 Jul - 19 Jul
This weekend
18 Jul - 20 Jul
Next weekend
25 Jul - 27 Jul

Top Holiday Rentals in Winchester

Idyllic Mt Sterling Retreat w/ Private Lake!
Stylish hallway with a door leading to a cozy room, adorned with framed artwork and a wooden railing.

Idyllic Mt Sterling Retreat w/ Private Lake!

2.0 star property
Idyllic Mt Sterling Retreat w/ Private Lake!
Exotic Animal Farm Stay in Illinois: Tour, Explore
Kitchen with wooden countertop, stainless steel sink, and white stove, offering ample space for cooking and dining.

Exotic Animal Farm Stay in Illinois: Tour, Explore

3.0 star property
Exotic Animal Farm Stay in Illinois: Tour, Explore
West Central Lodging
BBQ/picnic Area

West Central Lodging

2.5 star property
10.0 out of 10, Exceptional, (1)
"We had a wonderful time - very quiet country location, the manager is friendly but not invasive. First time I have heard a whippoorwill sing in many years. "
West Central Lodging
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

Can I find 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.

What’s there to see and do in Winchester?

While you're exploring the area, Lake Jacksonville and Jacksonville Community Park are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find Morgan County Fairgrounds and Illinois College.

What’s a holiday rental in Winchester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester. Holiday rentals offer extras such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for a family trip.