Winchester Vacation Rentals from ￥12,460: Search Short-Term Rentals

Q: 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.

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Vacation Rentals in Winchester

Cozy dining area with a wooden table and chairs, a patterned rug, and a refrigerator.

"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."

￥18,299 total

includes taxes & fees

Jul 20 - Jul 21

Kitchen area with a stainless steel sink, dishwasher, and ample countertop space.

"We had a great stay. The environment is just cuddling. "

￥18,315 total

includes taxes & fees

Jul 14 - Jul 15

Enjoy meals in this stylish dining area with a wooden table and matching chairs, surrounded by large windows and a decorative rug.

"We enjoyed our stay at this beautiful country home. "

￥29,994 total

includes taxes & fees

Jul 12 - Jul 13

Enjoy cooking in this well-equipped kitchen with a microwave, oven, and dishwasher.

"House was clean with lots of stuff to do! Very quiet get away"

￥18,315 total

includes taxes & fees

Jul 14 - Jul 15

Staircase leads to an upper level in a rustic cabin setting.

"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"

￥22,954 total

includes taxes & fees

Jul 15 - Jul 16

Relax by the serene fountain and enjoy the pool area with lounge chairs and potted plants.

"Fabulous"

Stunning hallway with framed artwork and a staircase leading to a cozy bedroom.

"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."

Relax on the porch with two comfortable chairs, surrounded by a deck and beautiful flower beds.

￥51,871 total

includes taxes & fees

Jul 21 - Jul 22

Welcome to a charming home with a cozy porch, complete with a white lattice railing and comfortable seating.

"Valarie’s VRBO is beautiful, Clean, Comfortable and great location!!! Cannot say enough!!"

Enjoy cooking in this well-equipped kitchen with a stove, oven, and ample counter space.

"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!"

￥22,721 total

includes taxes & fees

Jul 14 - Jul 15

Enjoy cooking in this well-equipped kitchen with a wooden countertop, stainless steel sink, and white stove.

Attached to a charming home, this garage offers ample space for a vehicle and additional storage.

"Clean and nice location"

Stylish hallway with a door leading to a cozy room, adorned with framed artwork and a wooden railing.

Kitchen with wooden countertop, stainless steel sink, and white stove, offering ample space for cooking and dining.

"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. "

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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!

Recent reviews of Winchester properties

5/5 Excellent

"Enjoyed my stay, very helpful. "

A verified traveler stayed at Green Acres Hotel

Posted 3 days ago

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

5/5 Excellent

Best little getaway!

"Our stay at the Llama Fun Guest House was incredible! We got to tour the grounds and meet the llamas and then relaxed in the very spacious and clean house! Kris and Terry were very welcoming and we felt right at home there. We will definitely be back!"

A verified traveler stayed at COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

Posted 4 days ago

5/5 Excellent

Home away from home

"The hotel is a little older, but very well maintained and clean. The staff was friendly and helpful. The breakfast was great and the beds were very comfy. We had the room with the jacuzzi tub and balcony overlooking the pool... very clean and spacious. We had a really nice time there!"

A verified traveler stayed at Best Western Jacksonville Inn

Posted 2 weeks ago

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.

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Winchester Vacation Rentals

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Vacation Rentals in Winchester

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

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

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

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

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

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

Idyllic Mt Sterling Retreat w/ Private Lake!

Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland

Home with great location

The Farmhouse Loft "Greene County's Guesthouse"

Exotic Animal Farm Stay in Illinois: Tour, Explore

Cozy 3 bedroom family friendly home in pike county IL

Spacious 6-bedroom house in wonderful Versailles with AC

Idyllic Mt Sterling Retreat w/ Private Lake!

Country Retreat in the heart of Pike County Illinois

Exotic Animal Farm Stay in Illinois: Tour, Explore

West Central Lodging

Find out more about Winchester

Recent reviews of Winchester properties

Green Acres Hotel

Hampton Inn Jacksonville

William Watson Hotel

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

Sleep Inn & Suites

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

Super 8 by Wyndham Jacksonville

Baymont by Wyndham Jacksonville

Best Western Jacksonville Inn

Frequently asked questions