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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

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, (26 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
28 Sep - 29 Sep
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)
"Very nice property"
United States
Brian G.
The price is AED 731
AED 853 total
includes taxes & fees
16 Oct - 17 Oct
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
2 bedrooms, desk, iron/ironing board, travel crib

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

The Farmhouse Loft "Greene County's Guesthouse"
Carrollton
9.8 out of 10, Exceptional, (63 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
28 Sep - 29 Sep
The Farmhouse Loft "Greene County's Guesthouse"
Exterior

4. 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
5 Oct - 6 Oct
Peace on the Prairie Too (Tiny House) -Pet Friendly. No pet fee or cleaning fee
Property grounds

5. 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
9.6 out of 10, Exceptional, (4 reviews)
"Property had all the amenities needed for a comfortable stay. Very private, quiet setting perfect for a relaxed stay."
United States
Chad L.
The price is AED 413
AED 710 total
includes taxes & fees
28 Sep - 29 Sep
3-bedroom country home in Pike Co Il with AC and heat
Exterior

6. 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 AED 474
AED 580 total
includes taxes & fees
29 Sep - 30 Sep
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
Property grounds

7. Peace on the Prairie — Quiet Nature Retreat on 23 Acres

Peace on the Prairie — Quiet Nature Retreat on 23 Acres
Murrayville
10.0 out of 10, Exceptional, (32 reviews)
"My wife and I spent a relaxing weekend at this property. The walking trail was a 10/10 for our pups. Everything about this place was amazing and we could not recommend it enough. Kevin went out of his way to make our check in as easy as possible."
United States
Catherine
The price is AED 380
AED 481 total
includes taxes & fees
28 Sep - 29 Sep
Peace on the Prairie — Quiet Nature Retreat on 23 Acres
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

Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville

8/10 Good
"Room was clean, staff was helpful. Some stains in the carpeting, typical for an older hotel. Could tell management worked to keep hotel maintained best as possible."
Michael 1-night trip
Posted 8 hours ago
Sleep Inn & Suites South Jacksonville

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’s there to see and do in Winchester?

While you're exploring the area, Jacksonville Community Park and Lake Jacksonville are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Illinois College and Future Champions Sport Complex.

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.