Winchester Holiday Rentals

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Holiday Rentals in Winchester

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!

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 AU$250
includes taxes & fees
11 Feb - 12 Feb
The Farmhouse Loft "Greene County's Guesthouse"

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

10.0 out of 10, Exceptional, (50)
"We stayed a few nights. House is clean and in very good shape. People are very nice and easy to work with."
The price is AU$352
includes taxes & fees
11 Feb - 12 Feb
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

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!

Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville

10.0 out of 10, Exceptional, (3)
"Absolutely loved our stay! Comfortable and cozy! Felt like we were staying in the Ingalls little house, but with modern conveniences. It really was a hidden gem! Can’t recommend enough! My only feedback is that the master bed wasn’t super comfy. Great stay and great host"
The price is AU$253
includes taxes & fees
9 Feb - 10 Feb
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville

Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL

10.0 out of 10, Exceptional, (2)
"Perfect spot for my spouse and I for an overnight stay. Clean and comfortable and just on the outskirts of town. We appreciated and loved the surprise coffee cake! "
The price is AU$186
includes taxes & fees
9 Feb - 10 Feb
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL

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

9.8 out of 10, Exceptional, (48)
"Cozy quiet location as described. The trails seem to be substantial, more than I had time for in a single evening. Very well-maintained accommodations. "
The price is AU$221
includes taxes & fees
23 Feb - 24 Feb
Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.

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

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

10.0 out of 10, Exceptional, (21)
"It was so peaceful and quiet. It was nice have hhe friendly cat i believe name is Nibs welcome us and even help us unpack. Wish we could have enjoyed it more as we were not there much as to only sleep. The only thing i would say is it was real hot sleeping that night and wasnt sure how to keep the fans on without the.light being left on in living room. Otherwise very nice thank you and God bless."
The price is AU$195
includes taxes & fees
13 Feb - 14 Feb
Peace on the Prairie: Native prairie setting - Pets allowed. No cleaning fees

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

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

Waterfront Cabin: Tranquil Setting in Mozier!

Waterfront Cabin: Tranquil Setting in Mozier!

Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland

2.0 star property
The price is AU$623
includes taxes & fees
17 Feb - 18 Feb
Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland

Exotic Animal Farm Stay in Illinois: Tour, Explore

Exotic Animal Farm Stay in Illinois: Tour, Explore

Exotic Animal Farm Stay in Illinois: Tour, Explore

3.0 star property
Exotic Animal Farm Stay in Illinois: Tour, Explore

Waterfront Cabin: Tranquil Setting in Mozier!

3.0 star property
Waterfront Cabin: Tranquil Setting in Mozier!

Idyllic Mt Sterling Retreat w/ Private Lake!

2.0 star property
Idyllic Mt Sterling Retreat w/ Private Lake!

West Central Lodging

2.5 star property
10.0 out of 10, Exceptional, (1)
"We had a wonderful time - very quiet country location, the manager is friendly but not invasive. First time I have heard a whippoorwill sing in many years. "
West Central Lodging
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 types of properties in Winchester you may be interested in

Sleep Inn & Suites

2.5 star property
9.4 out of 10, Exceptional, (473)
"Nice, clean place. No funny odors or mold. Seems fairly new. Reasonably priced. I’d stay again."
The price is AU$134
includes taxes & fees
13 Feb - 14 Feb
Sleep Inn & Suites

Best Western Jacksonville Inn

2.5 star property
8.4 out of 10, Very good, (632)
"It was super clean "
The price is AU$136
includes taxes & fees
16 Feb - 17 Feb
Best Western Jacksonville Inn

Quality Inn Jacksonville near I-72

2.5 star property
7.8 out of 10, Good, (355)
"Came in so tired that I didn't look around much! The bed was comfortable, the water was hot and the TV was easy to run. I appreciated the extra room to navigate in the accessible room. I did notice that the bottom of the bathroom door had been banged up by someone's wheelchair, but it was nice and clean. "
The price is AU$112
includes taxes & fees
9 Mar - 10 Mar
Quality Inn Jacksonville near I-72
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.

Frequently asked questions

Can I find holiday rentals in Winchester?

Yes, there are holiday rentals close to the most popular sights in Winchester, or you can select a more secluded option if you're looking for a relaxing stay.

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

Charming 3-bedroom house in Winchester with WiFi and AC: This highly rated holiday home rental in Winchester has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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 wider area, you’ll find Morgan County Fairgrounds and Illinois College.

What’s a holiday rental in Winchester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester. Holiday rentals offer extras such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for a family trip.