Winchester Vacation Rentals from ￥19,767: Search Short-Term Rentals

Q: What are some of the best vacation rentals that Winchester has to offer?

Cozy little house in town with country view on backdeck. : Visitors like this Winchester vacation home rental. It offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of books.

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Our top choices for Winchester vacation rentals

A dining area with a wooden table and chairs, a patterned rug, and a kitchen in the background.

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

Jacksonville

David W.

￥19,767 total

includes taxes & fees

Nov 4 - Nov 5

A two-story house with a wooden deck and a garden with colorful flowers.

2. COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

Bluffs

Brian G.

￥34,097 total

includes taxes & fees

Oct 25 - Oct 26

A two-story building with a balcony on the upper floor, a front door, and a sign that reads "Peace on the Prairie Klein Prairie".

3. Peace on the Prairie Too (Tiny House) -Pet Friendly. No pet fee or cleaning fee

Murrayville

Anonymous traveler

￥21,710 total

includes taxes & fees

Nov 4 - Nov 5

A rustic log cabin with a porch and a chimney.

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

Jacksonville

Dylan

￥24,771 total

includes taxes & fees

Oct 25 - Oct 26

A coffee and tea station with a coffee maker, mugs, and a tea kettle.

5. Peace on the Prairie — Quiet Nature Retreat on 23 Acres

Murrayville

Catherine

￥20,365 total

includes taxes & fees

Oct 27 - Oct 28

A kitchen with wooden cabinets, a granite countertop, a stainless steel sink, a black stove, and pendant lighting.

6. Peaceful Country Escape - High Speed Wifi

Pittsfield

￥35,744 total

includes taxes & fees

Oct 25 - Oct 26

A wooden deck with a railing, surrounded by trees with autumn foliage.

7. 3-bedroom country home in Pike Co Il with AC and heat

Chambersburg

Chad L.

￥33,086 total

includes taxes & fees

Nov 21 - Nov 22

A bedroom with a wooden headboard, a large bed with white bedding, a bench, and a dresser with a mirror.

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

Carrollton

Debbie S.

￥25,769 total

includes taxes & fees

Oct 25 - Oct 26

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Top Winchester Hotel Reviews

Holiday Inn Express Hotel & Suites Jacksonville by IHG

8/10 Good

"The air conditioner/heater did not work very well. One staff member told me the water was free to IHG members while another staff member told me they were not free. Everyone working needs to be on the same sheet of music."

Peace on the Prairie — Quiet Nature Retreat on 23 Acres

10/10 Excellent

"Kevin was very prompt to respond to my message & was over in a couple minutes. I stayed at the apartment, clean, cozy & good cookies! I had my dog with me & we both loved exploring the property. It was / is a super peaceful getaway for however long you choose to stay, plan on returning in spring & staying a day or 2 longer than the 2 night stay we just did. My only complaint was not enough cookies, lol! I can’t recommend this peaceful retreat enough"

Sleep Inn & Suites South Jacksonville

8/10 Good

"The staff at the hotel is super nice and very helpful. It’s seems there are less of them, though, compared to when we have visited in the past. Our room overall was very clean, but the shower head was covered with black mold, so we opted to shower at the home of the people we were visiting."

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

10/10 Excellent

"This is THEE sweetest place to stay for any couple or solo traveler who loves a peaceful country setting. And the fresh baked apple cinnamon coffee cake was amazing-so nice of the hosts. The bunkhouse was immaculate; it had everything we could want. The sunrise over the fields was fabulous. The location fit our needs-close to Jacksonville for dining and close to Winchester where I had a class. My husband and I would stay here again."

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?

Cozy little house in town with country view on backdeck.: Visitors like this Winchester vacation home rental. It offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of books.

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.

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Check prices for these dates

Our top choices for Winchester vacation rentals

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

2. COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

3. Peace on the Prairie Too (Tiny House) -Pet Friendly. No pet fee or cleaning fee

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

5. Peace on the Prairie — Quiet Nature Retreat on 23 Acres

6. Peaceful Country Escape - High Speed Wifi

7. 3-bedroom country home in Pike Co Il with AC and heat

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

Find vacation rentals that suit your style

Top Winchester Hotel Reviews

Holiday Inn Express Hotel & Suites Jacksonville by IHG

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

Rodeway Inn Pittsfield

Peace on the Prairie — Quiet Nature Retreat on 23 Acres

Sleep Inn & Suites South Jacksonville

Monroe Street Suites

Super 8 by Wyndham Jacksonville

Hampton Inn Jacksonville

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

Find out more about Winchester

Frequently asked questions

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