Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for Winchester vacation rentals

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 ￥15,734
￥20,044 total
includes taxes & fees
May 29 - May 30
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
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 ￥17,630
￥22,061 total
includes taxes & fees
Jun 10 - Jun 11
Peace on the Prairie Too (Tiny House) -Pet Friendly. No pet fee or cleaning fee
2 bedrooms, desk, iron/ironing board, travel crib

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 ￥13,509
￥26,107 total
includes taxes & fees
Jun 15 - Jun 16
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 ￥19,072
￥23,582 total
includes taxes & fees
Jun 16 - Jun 17
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, (60 reviews)
"Beautiful place, highly recommend "
United States
Anthony S.
The price is ￥28,464
￥34,545 total
includes taxes & fees
Jun 1 - Jun 2
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
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 ￥20,502
￥25,097 total
includes taxes & fees
May 31 - Jun 1
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
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 ￥20,502
￥29,308 total
includes taxes & fees
May 28 - May 29
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 ￥39,907
￥55,768 total
includes taxes & fees
May 28 - May 29
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

Holiday Inn Express Hotel & Suites Jacksonville by IHG

Holiday Inn Express Hotel & Suites Jacksonville by IHG

10/10 Excellent
"My room was clean, the staff was wonderful. The sweet lady who works the breakfast was an absolute huge help for us. She was so kind! We were able to hangout in the lobby and utilize the swimming pool. Breakfast was really good too!"
Brook 2-night trip
Posted 20 hours ago
Holiday Inn Express Hotel & Suites Jacksonville by IHG

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 vacation rentals in Winchester?

Yes, you can find vacation rentals near top points of interest in Winchester, or you can select a secluded option if you want a relaxing place to stay.

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

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!: Visitors like this Winchester vacation home rental. It 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like 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 larger area, you’ll find Morgan County Fairgrounds and Illinois College.

What’s a vacation rental in Winchester like?

Vacation rentals are privately owned properties you can stay in for several days or longer in Winchester. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy front desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for a family getaway.