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Winchester Holiday Rentals

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Winchester holiday rentals

A dining area with a wooden table and chairs, a patterned rug, and a kitchen in the background.

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

Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Jacksonville
10.0 out of 10, Exceptional, (26 reviews)
"Really enjoyed our stay. The place was very clean and bed really comfortable "
United States
David W.
The price is HK$776
HK$989 total
includes taxes & fees
13 Sept - 14 Sept
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
A coffee maker on a counter, a framed picture of a boat on water, and a coffee bag on the wall.

2. Peace on the Prairie — Quiet Nature Retreat on 24 Acres

Peace on the Prairie — Quiet Nature Retreat on 24 Acres
Murrayville
10.0 out of 10, Exceptional, (31 reviews)
"Exactly as described, wonderful experience."
United States
Petraborg P.
The price is HK$727
HK$936 total
includes taxes & fees
8 Sept - 9 Sept
Peace on the Prairie — Quiet Nature Retreat on 24 Acres
A two-story building with a balcony on the upper floor, a front door, and a sign that reads "Peace on the Prairie Klein Prairie".

3. Peace on the Prairie Too (Tiny House) -Pet Friendly. No pet fee or cleaning fee

Peace on the Prairie Too (Tiny House) -Pet Friendly. No pet fee or cleaning fee
Murrayville
9.8 out of 10, Exceptional, (69 reviews)
"Kevin was a great host. Responsive when I had issues with the lock. Great homemade cookies. "
United States
Anonymous traveller
The price is HK$868
HK$1,086 total
includes taxes & fees
9 Sept - 10 Sept
Peace on the Prairie Too (Tiny House) -Pet Friendly. No pet fee or cleaning fee
A wooden deck with a railing, surrounded by trees with autumn foliage.

4. 3-bedroom country home in Pike Co Il with AC and heat

3-bedroom country home in Pike Co Il with AC and heat
Chambersburg
10.0 out of 10, Exceptional, (2 reviews)
"If you like quiet, wildlife and beautiful trees, this is the perfect place. We loved our stay! Thanks to our host!"
United States
Carol
The price is HK$882
HK$1,525 total
includes taxes & fees
10 Sept - 11 Sept
3-bedroom country home in Pike Co Il with AC and heat
A rustic log cabin with a porch and a chimney.

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

Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
Jacksonville
10.0 out of 10, Exceptional, (17 reviews)
"The place was really neat and the host was incredibly friendly"
United States
Dylan
The price is HK$1,011
HK$1,238 total
includes taxes & fees
15 Sept - 16 Sept
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
A bedroom with a wooden headboard, a large bed with white bedding, a bench, and a dresser with a mirror.

6. The Farmhouse Loft "Greene County's Guesthouse"

The Farmhouse Loft "Greene County's Guesthouse"
Carrollton
9.8 out of 10, Exceptional, (62 reviews)
"Stayed at the Farmhouse Loft for a local wedding. It met all our expectations. Great location on the town square. Will definitely stay there again "
United States
Gregory D.
The price is HK$666
HK$1,288 total
includes taxes & fees
8 Sept - 9 Sept
The Farmhouse Loft "Greene County's Guesthouse"
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

Best Western Jacksonville Inn

Best Western Jacksonville Inn

8/10 Good
"Could be just a little cleaner and really could have used a handicap room"
Heather 2-night trip
Posted 14 hours ago
Best Western Jacksonville Inn

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

  • View our selection of featured holiday rentals in Winchester
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Look no further and take a look at our great range of rental properties in Winchester!

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.