Winchester Holiday Rentals
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Our top choices for Winchester holiday rentals
1. Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, ILJacksonville
10.0 out of 10, Exceptional, (28 reviews)
"Really enjoyed our stay. The place was very clean and bed really comfortable "
David W.
The price is HK$777
HK$990 total
includes taxes & fees
24 Oct - 25 Oct
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"
Brian G.
The price is HK$1,405
HK$1,706 total
includes taxes & fees
24 Oct - 25 Oct
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 feeMurrayville
9.8 out of 10, Exceptional, (70 reviews)
"Kevin was a great host. Responsive when I had issues with the lock. Great homemade cookies. "
Anonymous traveller
The price is HK$869
HK$1,087 total
includes taxes & fees
31 Oct - 1 Nov
4. Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
Audrey's Abode - Restored log cabin, country setting, minutes from JacksonvilleJacksonville
10.0 out of 10, Exceptional, (17 reviews)
"The place was really neat and the host was incredibly friendly"
Dylan
The price is HK$1,012
HK$1,239 total
includes taxes & fees
25 Oct - 26 Oct
5. Peace on the Prairie — Quiet Nature Retreat on 23 Acres
Peace on the Prairie — Quiet Nature Retreat on 23 AcresMurrayville
10.0 out of 10, Exceptional, (33 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."
Catherine
The price is HK$791
HK$1,005 total
includes taxes & fees
26 Oct - 27 Oct
The price is HK$1,177
HK$1,946 total
includes taxes & fees
23 Oct - 24 Oct
7. 3-bedroom country home in Pike Co Il with AC and heat
3-bedroom country home in Pike Co Il with AC and heatChambersburg
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."
Chad L.
The price is HK$981
HK$1,638 total
includes taxes & fees
21 Nov - 22 Nov
8. The Farmhouse Loft "Greene County's Guesthouse"
The Farmhouse Loft "Greene County's Guesthouse"Carrollton
9.8 out of 10, Exceptional, (63 reviews)
"Very cute place!!!"
Debbie S.
The price is HK$667
HK$1,289 total
includes taxes & fees
18 Nov - 19 Nov
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
Rodeway Inn Pittsfield
8/10 Good
Find out more about Winchester
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