Winchester Vacation Rentals

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Vacation Rentals in Winchester

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

10.0 out of 10, Exceptional, (8)
"Very nice and cozy cabin in the middle of a cornfield. This place is close to town but completely isolated. We sat on the front porch and enjoyed our morning coffee in almost complete silence. Not sure if this is the place for everyone, but it was perfect for us."
The price is ¥14,478
¥18,299 total
includes taxes & fees
Jul 20 - Jul 21
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL

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

10.0 out of 10, Exceptional, (24)
"We had a great stay. The environment is just cuddling. "
The price is ¥14,512
¥18,315 total
includes taxes & fees
Jul 14 - Jul 15
Peace on the Prairie: Native prairie setting - Pets allowed. No cleaning fees

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

10.0 out of 10, Exceptional, (54)
"We enjoyed our stay at this beautiful country home. "
The price is ¥26,192
¥29,994 total
includes taxes & fees
Jul 12 - Jul 13
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

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

9.8 out of 10, Exceptional, (52)
"House was clean with lots of stuff to do! Very quiet get away"
The price is ¥14,512
¥18,315 total
includes taxes & fees
Jul 14 - Jul 15
Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.

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

10.0 out of 10, Exceptional, (5)
"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 ¥18,865
¥22,954 total
includes taxes & fees
Jul 15 - Jul 16
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville

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

9.8 out of 10, Exceptional, (73)
"Fabulous"
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!

Idyllic Mt Sterling Retreat w/ Private Lake!

10.0 out of 10, Exceptional, (7)
"It was a delightful stay - games on the patio, corn hole on the desk, swimming, fishing, walks, and sitting around the fire. Also, we greatly appreciated the ample fridge and freezer space."
Idyllic Mt Sterling Retreat w/ Private Lake!

Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland

2.0 star property
The price is ¥36,721
¥51,871 total
includes taxes & fees
Jul 21 - Jul 22
Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland

Home with great location

10.0 out of 10, Exceptional, (19)
"Valarie’s VRBO is beautiful, Clean, Comfortable and great location!!! Cannot say enough!!"
Home with great location

The Farmhouse Loft "Greene County's Guesthouse"

9.8 out of 10, Exceptional, (55)
"We were in the area for a couple days for an event in Roadhouse. Carrollton was incredibly charming and we really loved the Farmhouse loft. We got food at the pizza place next door and I had the BEST meatball sub! We really appreciated being able to bring our dog along on our trip as he can be very anxious when we are away. Can't wait to come back!"
The price is ¥12,460
¥22,721 total
includes taxes & fees
Jul 14 - Jul 15
The Farmhouse Loft "Greene County's Guesthouse"

Exotic Animal Farm Stay in Illinois: Tour, Explore

Exotic Animal Farm Stay in Illinois: Tour, Explore

Cozy 3 bedroom family friendly home in pike county IL

10.0 out of 10, Exceptional, (3)
"Clean and nice location"
Cozy 3 bedroom family friendly home in pike county IL

Spacious 6-bedroom house in wonderful Versailles with AC

Spacious 6-bedroom house in wonderful Versailles with AC

Idyllic Mt Sterling Retreat w/ Private Lake!

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

Country Retreat in the heart of Pike County Illinois

Country Retreat in the heart of Pike County Illinois

Exotic Animal Farm Stay in Illinois: Tour, Explore

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

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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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 Jacksonville Community 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.