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Top Holiday Rentals in Winchester

Our top choices for Winchester holiday rentals

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!

9.8 out of 10, Exceptional, (77)
"Fabulous"
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!

Peace on the Prairie: Native prairie setting - Pets allowed. No cleaning fees

10.0 out of 10, Exceptional, (24)
"We had a great stay. The environment is just cuddling. "
The price is £94
includes taxes & fees
1 Sept - 2 Sept
Peace on the Prairie: Native prairie setting - Pets allowed. No cleaning fees

Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL

10.0 out of 10, Exceptional, (10)
"Very nice and cozy cabin in the middle of a cornfield. This place is close to town but completely isolated. We sat on the front porch and enjoyed our morning coffee in almost complete silence. Not sure if this is the place for everyone, but it was perfect for us."
The price is £96
includes taxes & fees
21 Aug - 22 Aug
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL

Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.

9.8 out of 10, Exceptional, (52)
"House was clean with lots of stuff to do! Very quiet get away"
The price is £96
includes taxes & fees
21 Aug - 22 Aug
Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.

Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville

10.0 out of 10, Exceptional, (7)
"The cabin is perfect for creating a relaxing atmosphere. We always like our stay there."
The price is £120
includes taxes & fees
25 Aug - 26 Aug
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville

Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland

2.0 star property
The price is £265
includes taxes & fees
22 Aug - 23 Aug
Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland

Home with great location

10.0 out of 10, Exceptional, (20)
"Great stay for our family - thank you!"
Home with great location

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

10.0 out of 10, Exceptional, (55)
"We enjoyed our stay at this beautiful country home. "
The price is £164
includes taxes & fees
21 Aug - 22 Aug
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

Spacious 6-bedroom house in rural Versailles with many amenities included.

10.0 out of 10, Exceptional, (1)
"We stayed for our Mendota FFA Chapter Officer Retreat. It was very accommodating for our group of nine high school students and two adult chaperones. The house itself is a bit chopped up, but has a lot of charm and many unique decor elements. The bar/kitchen was very unique. We utilized both outdoor grill and firepit area to prepare evening meals. The pool table in the basement was a big hit with the boys. Air fresheners were a little overpowering. "
Spacious 6-bedroom house in rural Versailles with many amenities included.

Idyllic Mt Sterling Retreat w/ Private Lake!

10.0 out of 10, Exceptional, (7)
"Wonder!! House and lake amazing! Kitchen well stocked with everything one would need! So many outside adventures! We had a wonderful time. Thank you. "
Idyllic Mt Sterling Retreat w/ Private Lake!

The Farmhouse Loft "Greene County's Guesthouse"

9.8 out of 10, Exceptional, (56)
"We were in the area for a couple days for an event in Roadhouse. Carrollton was incredibly charming and we really loved the Farmhouse loft. We got food at the pizza place next door and I had the BEST meatball sub! We really appreciated being able to bring our dog along on our trip as he can be very anxious when we are away. Can't wait to come back!"
The price is £125
includes taxes & fees
27 Aug - 28 Aug
The Farmhouse Loft "Greene County's Guesthouse"

Country Retreat in the heart of Pike County Illinois

Country Retreat in the heart of Pike County Illinois

Exotic Animal Farm Stay in Illinois: Tour, Explore

Exotic Animal Farm Stay in Illinois: Tour, Explore

Cozy 3 bedroom family friendly home in pike county IL

10.0 out of 10, Exceptional, (3)
"Clean and nice location"
Cozy 3 bedroom family friendly home in pike county IL

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

3.0 star property
Exotic Animal Farm Stay in Illinois: Tour, Explore

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

Waterfront cottage in Calhoun County, IL

The price is £225
includes taxes & fees
1 Sept - 2 Sept
Waterfront cottage in Calhoun County, IL
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

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 are some of the best holiday rentals that Winchester has to offer?

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!: This holiday home rental outside of Winchester is located in a rural location, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

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.