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Compare 7 Vacation Homes in Winchester with updated reviews, rates, and availability.

Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.

9.8 out of 10, Exceptional, (51)
"I had such a great stay here with my dogs. The place had everything we needed and then some. The property is beautiful and I was lucky the weather cooperated so we could walk through the trails and I could take some pictures of the many birds in the area. I will definitely be back. Thank you!"
The price is AED 404
AED 502 total
includes taxes & fees
4 Apr - 5 Apr
Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

10.0 out of 10, Exceptional, (51)
"We enjoyed our stay at this beautiful country home. "
The price is AED 731
AED 837 total
includes taxes & fees
4 Apr - 5 Apr
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

Home with great location

10.0 out of 10, Exceptional, (16)
"This is one of the best we have ever stayed at. Great neighborhood. Cozy home. Everything and anything you could possible want or need is there. Cute decor. Comfy beds. Our stay was wonderful. Thank you."
Home with great location

Idyllic Mt Sterling Retreat w/ Private Lake!

10.0 out of 10, Exceptional, (5)
"My brother and our families (4 adults, 5 teens) stayed at the Hideaway along with our 2 dogs. Great place! Plenty of comfortable beds for all to have their own space. Living room area and the large dining table was great for playing board games. The dogs (and kids) loved running around in the woods and around the lake. The kitchen is massive, with plenty of room for multiple people to cook and well stocked with every type of pan, utensil or sharp knife you might need! We definitely will...
Idyllic Mt Sterling Retreat w/ Private Lake!

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!

9.8 out of 10, Exceptional, (71)
"Thanks for having us"
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!

Cozy 3 bedroom family friendly home in pike county IL

10.0 out of 10, Exceptional, (2)
"The house was older as expected in Pleasant Hill. Very quiet neighborhood and ample space. Stayed three nights everything was as expected. Owners were awesome and responsive. We have booked for two more stays in the fall. Everything is close for groceries. "
Cozy 3 bedroom family friendly home in pike county IL

5 Bedroom Lodge in Illinois

9.8 out of 10, Exceptional, (29)
"Wonderful property, great hosts. We will be back."
5 Bedroom Lodge in Illinois
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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Other property types in Winchester

The Farmhouse Loft "Greene County's Guesthouse"

9.8 out of 10, Exceptional, (53)
"We had an overnight stay during a very long roadtrip, the loft was perfect and we were able to have a very relaxing night after eating some of the best pizza I have ever had, highly recommend the place just a few hundred feet away. Communication with owners was perfect."
The price is AED 312
AED 569 total
includes taxes & fees
6 Apr - 7 Apr
The Farmhouse Loft "Greene County's Guesthouse"

Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.

9.8 out of 10, Exceptional, (51)
"I had such a great stay here with my dogs. The place had everything we needed and then some. The property is beautiful and I was lucky the weather cooperated so we could walk through the trails and I could take some pictures of the many birds in the area. I will definitely be back. Thank you!"
The price is AED 404
AED 502 total
includes taxes & fees
4 Apr - 5 Apr
Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.

Peace on the Prairie: Native prairie setting - Pets allowed. No cleaning fees

10.0 out of 10, Exceptional, (21)
"We had a great stay. The environment is just cuddling. "
The price is AED 349
AED 443 total
includes taxes & fees
4 Apr - 5 Apr
Peace on the Prairie: Native prairie setting - Pets allowed. No cleaning fees
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.