Winchester Vacation Rentals

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Check prices for these dates

Tonight
Sep 25 - Sep 26
Tomorrow
Sep 26 - Sep 27
This weekend
Sep 26 - Sep 28
Next weekend
Oct 3 - Oct 5

Vacation Rentals in Winchester

Peaceful studio retreat surrounded by prairie, wildlife, and open skies.
Fridge, microwave, oven, stovetop

Peaceful studio retreat surrounded by prairie, wildlife, and open skies.

10.0 out of 10, Exceptional, (24)
"We had a great stay. The environment is just cuddling. "
The price is ￥10,849
￥14,653 total
includes taxes & fees
Oct 6 - Oct 7
Peaceful studio retreat surrounded by prairie, wildlife, and open skies.
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
Dining

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

10.0 out of 10, Exceptional, (58)
"We enjoyed our stay at this beautiful country home. "
The price is ￥26,654
￥31,561 total
includes taxes & fees
Sep 28 - Sep 29
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (55)
"Exactly what we needed. Peaceful, secluded, and relaxing! The trails are an added bonus. The respect for nature, pets, and people spoke to us, which are evident in the aesthetic of the property. We come to Jacksonville often and will definitely be back!"
The price is ￥11,425
￥15,238 total
includes taxes & fees
Oct 7 - Oct 8
Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
Interior

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

10.0 out of 10, Exceptional, (8)
"The cabin is perfect for creating a relaxing atmosphere. We always like our stay there."
The price is ￥19,198
￥23,500 total
includes taxes & fees
Sep 28 - Sep 29
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
Terrace/patio

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

9.8 out of 10, Exceptional, (79)
"Fabulous"
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Dining

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

10.0 out of 10, Exceptional, (13)
"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 ￥14,733
￥18,769 total
includes taxes & fees
Sep 28 - Sep 29
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Home with great location
Exterior

Home with great location

10.0 out of 10, Exceptional, (20)
"Great stay for our family - thank you!"
Home with great location
Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland
Exterior

Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland

2.0 star property
The price is ￥37,065
￥51,953 total
includes taxes & fees
Sep 26 - Sep 27
Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland
Spacious 6-bedroom house in rural Versailles with many amenities included.
Exterior

Spacious 6-bedroom house in rural Versailles with many amenities included.

10.0 out of 10, Exceptional, (1)
"We stayed for our Mendota FFA Chapter Officer Retreat. It was very accommodating for our group of nine high school students and two adult chaperones. The house itself is a bit chopped up, but has a lot of charm and many unique decor elements. The bar/kitchen was very unique. We utilized both outdoor grill and firepit area to prepare evening meals. The pool table in the basement was a big hit with the boys. Air fresheners were a little overpowering. "
Spacious 6-bedroom house in rural Versailles with many amenities included.
Country Retreat in the heart of Pike County Illinois
Interior

Country Retreat in the heart of Pike County Illinois

Country Retreat in the heart of Pike County Illinois
The Farmhouse Loft "Greene County's Guesthouse"
Fridge, microwave, oven, stovetop

The Farmhouse Loft "Greene County's Guesthouse"

9.8 out of 10, Exceptional, (57)
"Very cute place!!!"
The price is ￥12,650
￥24,447 total
includes taxes & fees
Oct 19 - Oct 20
The Farmhouse Loft "Greene County's Guesthouse"
Idyllic Mt Sterling Retreat w/ Private Lake!
House (4 Bedrooms) | Interior

Idyllic Mt Sterling Retreat w/ Private Lake!

2.0 star property
Idyllic Mt Sterling Retreat w/ Private Lake!
Exotic Animal Farm Stay in Illinois: Tour, Explore
House (1 Bedroom) | Interior

Exotic Animal Farm Stay in Illinois: Tour, Explore

3.0 star property
Exotic Animal Farm Stay in Illinois: Tour, Explore
West Central Lodging
BBQ/picnic area

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
Charming 2-bedroom barnloft on hobby farm in Pleasant Hill pittsfield area
Property grounds

Charming 2-bedroom barnloft on hobby farm in Pleasant Hill pittsfield area

The price is ￥17,278
￥24,621 total
includes taxes & fees
Sep 26 - Sep 27
Charming 2-bedroom barnloft on hobby farm in Pleasant Hill pittsfield area
Dave’s River House
Microwave, oven, stovetop

Dave’s River House

The price is ￥14,761
￥34,058 total
includes taxes & fees
Oct 1 - Oct 2
Dave’s River House
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

Sleep Inn & Suites

10/10 Excellent
"What really made this stay wonderful was staff. They made us feel welcome from the minute we stepped in the door. Friendly smiles, welcoming conversations and great recommendations for activities. I'd specifically like to thank Tyler for going above and beyond for making us feel welcome and relaxed after a long drive. The hotel was clean, it was quiet and had a sneakily good breakfast! World class! Will stay again. "
Jason 1-night trip
Posted 3 days ago
Sleep Inn & Suites

Find out more about Winchester

Find out more about Winchester

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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?

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!: Visitors like this Winchester vacation home rental. It is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

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.