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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Winchester vacation rentals

Dining

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, (22 reviews)
"Really enjoyed our stay. The place was very clean and bed really comfortable "
United States
David W.
The price is AED 364
AED 463 total
includes taxes & fees
11 Aug - 12 Aug
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Exterior

2. COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
Bluffs
10.0 out of 10, Exceptional, (64 reviews)
"Beautiful place, highly recommend "
United States
Anthony S.
The price is AED 731
AED 876 total
includes taxes & fees
9 Sep - 10 Sep
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
Exterior

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 traveler
The price is AED 407
AED 509 total
includes taxes & fees
21 Aug - 22 Aug
Peace on the Prairie Too (Tiny House) -Pet Friendly. No pet fee or cleaning fee
Exterior

4. 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, (16 reviews)
"Was an excellent place to stay for the weekend."
United States
Amanda
The price is AED 474
AED 580 total
includes taxes & fees
11 Aug - 12 Aug
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
2 bedrooms, desk, iron/ironing board, travel crib

5. 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 AED 312
AED 603 total
includes taxes & fees
16 Aug - 17 Aug
The Farmhouse Loft "Greene County's Guesthouse"
Dining

6. 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 AED 455
AED 561 total
includes taxes & fees
8 Sep - 9 Sep
Peace on the Prairie — Quiet Nature Retreat on 24 Acres
Property grounds

7. 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
"Would go back here many times over again. Was exactly what we needed."
United States
Jake O.
The price is AED 413
AED 714 total
includes taxes & fees
23 Aug - 24 Aug
3-bedroom country home in Pike Co Il with AC and heat
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

10/10 Excellent
"Clean hotel"
Menwoe 1-night trip
Posted 3 days ago
Jacksonville Inn & Suites

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 King 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.