Winchester Holiday Rentals

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Check prices for these dates

In two weeks
5 Jun - 7 Jun
In two months
17 Jul - 19 Jul
In three months
14 Aug - 16 Aug
In four months
11 Sept - 13 Sept

Our top choices for Winchester holiday rentals

Exterior

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, (65 reviews)
"We had such a great experience staying here. The property was beautiful and the hosts were very welcoming and friendly. The property was very pet friendly as well. We will definitely go back for the peace and quiet!"
United States
Mandy S.
The price is HK$867
HK$1,085 total
includes taxes & fees
31 May - 1 Jun
Peace on the Prairie Too (Tiny House) -Pet Friendly. No pet fee or cleaning fee
Exterior

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, (13 reviews)
"Was an excellent place to stay for the weekend."
United States
Amanda
The price is HK$1,011
HK$1,237 total
includes taxes & fees
25 May - 26 May
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
2 bedrooms, desk, iron/ironing board, travel cot

The Farmhouse Loft "Greene County's Guesthouse"

The Farmhouse Loft "Greene County's Guesthouse"
Carrollton
9.8 out of 10, Exceptional, (61 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$1,287 total
includes taxes & fees
3 Jun - 4 Jun
The Farmhouse Loft "Greene County's Guesthouse"
Dining

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, (30 reviews)
"Yes, everything was very nice"
United States
Cary W.
The price is HK$853
HK$1,070 total
includes taxes & fees
24 May - 25 May
Peace on the Prairie — Quiet Nature Retreat on 24 Acres
Exterior

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
Bluffs
10.0 out of 10, Exceptional, (59 reviews)
"Beautiful place, highly recommend "
United States
Anthony S.
The price is HK$1,403
HK$1,695 total
includes taxes & fees
5 Jun - 6 Jun
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
Dining

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, (18 reviews)
"Always a nice place to stay."
United States
Pete D.
The price is HK$776
HK$988 total
includes taxes & fees
27 May - 28 May
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Interior

Charming 2-bedroom barnloft on hobby farm in Pleasant Hill pittsfield area

Charming 2-bedroom barnloft on hobby farm in Pleasant Hill pittsfield area
Pleasant Hill
The price is HK$1,011
HK$1,461 total
includes taxes & fees
24 May - 25 May
Charming 2-bedroom barnloft on hobby farm in Pleasant Hill pittsfield area
Exterior

Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland

Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland
Pittsfield
The price is HK$1,967
HK$2,749 total
includes taxes & fees
27 May - 28 May
Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland
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

Jacksonville Inn & Suites

Jacksonville Inn & Suites

4/10 Poor
"Didn't have anything hot for breakfast"
Jeff 1-night trip
Posted 9 hours ago
Jacksonville Inn & Suites

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:

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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?

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!: This holiday home rental outside of Winchester offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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.