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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Winchester vacation rentals

Dining

1. 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, (26 reviews)
"Really enjoyed our stay. The place was very clean and bed really comfortable "
United States
David W.
The price is ￥15,470
￥19,708 total
includes taxes & fees
Sep 13 - Sep 14
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Dining

2. 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, (31 reviews)
"Exactly as described, wonderful experience."
United States
Petraborg P.
The price is ￥14,626
￥18,814 total
includes taxes & fees
Sep 15 - Sep 16
Peace on the Prairie — Quiet Nature Retreat on 24 Acres
Exterior

3. 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, (69 reviews)
"Kevin was a great host. Responsive when I had issues with the lock. Great homemade cookies. "
United States
Anonymous traveler
The price is ￥17,298
￥21,645 total
includes taxes & fees
Sep 9 - Sep 10
Peace on the Prairie Too (Tiny House) -Pet Friendly. No pet fee or cleaning fee
Property grounds

4. 3-bedroom country home in Pike Co Il with AC and heat

3-bedroom country home in Pike Co Il with AC and heat
Chambersburg
10.0 out of 10, Exceptional, (2 reviews)
"If you like quiet, wildlife and beautiful trees, this is the perfect place. We loved our stay! Thanks to our host!"
United States
Carol
The price is ￥17,579
￥30,389 total
includes taxes & fees
Sep 10 - Sep 11
3-bedroom country home in Pike Co Il with AC and heat
Exterior

5. 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, (17 reviews)
"The place was really neat and the host was incredibly friendly"
United States
Dylan
The price is ￥20,158
￥24,675 total
includes taxes & fees
Sep 15 - Sep 16
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
2 bedrooms, desk, iron/ironing board, travel crib

6. The Farmhouse Loft "Greene County's Guesthouse"

The Farmhouse Loft "Greene County's Guesthouse"
Carrollton
9.8 out of 10, Exceptional, (62 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 ￥13,282
￥25,669 total
includes taxes & fees
Sep 8 - Sep 9
The Farmhouse Loft "Greene County's Guesthouse"
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

Best Western Jacksonville Inn

Best Western Jacksonville Inn

8/10 Good
"Could be just a little cleaner and really could have used a handicap room"
Heather 2-night trip
Posted 18 hours ago
Best Western Jacksonville Inn

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

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Look no further and take a look at our great range of rental properties in Winchester!

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!: You might want to consider this vacation home rental near Winchester, which 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.