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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Winchester vacation rentals

2 bedrooms, desk, iron/ironing board, travel crib

The Farmhouse Loft "Greene County's Guesthouse"

The Farmhouse Loft "Greene County's Guesthouse"
Carrollton
9.8 out of 10, Exceptional, (61 reviews)
"Stayed at the Farmhouse Loft for a local wedding. It met all our expectations. Great location on the town square. Will definitely stay there again "
United States
Gregory D.
The price is AED 312
AED 603 total
includes taxes & fees
28 Jun - 29 Jun
The Farmhouse Loft "Greene County's Guesthouse"
Dining

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

Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Jacksonville
10.0 out of 10, Exceptional, (20 reviews)
"Always a nice place to stay."
United States
Pete D.
The price is AED 364
AED 463 total
includes taxes & fees
29 Jun - 30 Jun
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Dining

Peace on the Prairie — Quiet Nature Retreat on 24 Acres

Peace on the Prairie — Quiet Nature Retreat on 24 Acres
Murrayville
10.0 out of 10, Exceptional, (30 reviews)
"Super easy access, great little place with everything I needed. It's too bad I was staying in winter, because I bet it's super nice when everything is blooming and the bees are buzzing. "
United States
Tanya A.
The price is AED 387
AED 488 total
includes taxes & fees
29 Jun - 30 Jun
Peace on the Prairie — Quiet Nature Retreat on 24 Acres
Exterior

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 fee
Murrayville
9.8 out of 10, Exceptional, (66 reviews)
"We had such a great experience staying here. The property was beautiful and the hosts were very welcoming and friendly. The property was very pet friendly as well. We will definitely go back for the peace and quiet!"
United States
Mandy S.
The price is AED 407
AED 509 total
includes taxes & fees
1 Jul - 2 Jul
Peace on the Prairie Too (Tiny House) -Pet Friendly. No pet fee or cleaning fee
Interior

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

Charming 2-bedroom barnloft on hobby farm in Pleasant Hill pittsfield area
Pleasant Hill
The price is AED 474
AED 685 total
includes taxes & fees
25 Jun - 26 Jun
Charming 2-bedroom barnloft on hobby farm in Pleasant Hill pittsfield area
Fridge, microwave, oven, stovetop

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

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
Griggsville
9.8 out of 10, Exceptional, (80 reviews)
"Wonderful venue with something for everyone to enjoy. "
United States
Karen T.
The price is AED 15,427
AED 20,207 total
includes taxes & fees
23 Jul - 24 Jul
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
Exterior

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
Bluffs
10.0 out of 10, Exceptional, (62 reviews)
"Beautiful place, highly recommend "
United States
Anthony S.
The price is AED 658
AED 798 total
includes taxes & fees
25 Jun - 26 Jun
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
Exterior

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

Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
Jacksonville
10.0 out of 10, Exceptional, (15 reviews)
"Was an excellent place to stay for the weekend."
United States
Amanda
The price is AED 474
AED 580 total
includes taxes & fees
28 Jun - 29 Jun
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
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 South Jacksonville

Sleep Inn & Suites South Jacksonville

10/10 Excellent
"Very nice facility, the only disappointment was the pool was closed"
Natalie 1-night trip
Posted 1 day ago
Sleep Inn & Suites South Jacksonville

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.