Holiday rentals in Pinckneyville

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Top-rated holiday rentals in Pinckneyville

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Top guest favourite
Home in Ava
4.93 out of 5 average rating, 132 reviews

JGB’s Farm and Getaway

We are in the country next to a blacktop road.This is a very laidback place , there are farm animals across the road at our farm. This was my moms farm house and I just want people to enjoy it as much as she did. We are close to Kincaid Lake, the local winerie, the World Shooting Complex, and hiking trails (Piney Creek Revenue). Come and enjoy a day fishing or just sitting on the back deck enjoying the peaceful surroundings. Later build a fire and sit back and relax. Come and enjoy the country.

Guest favourite
A cozy bedroom is featured with warm wood paneling and a metal ceiling. A spacious bed with soft linens is positioned near a window. A comfortable armchair and a nightstand with a lamp are included, contributing to the inviting ambience.
Tiny home in Whittington
4.91 out of 5 average rating, 308 reviews

Tiny Home of Whittington

This cozy tiny home is located a little over one mile off of Interstate 57 and within two miles of Rend Lake. Whether traveling through and needing an easy one night stay or a weekend getaway, this is the place for you. Located in the quiet village of Whittington, the property has great access to the area while providing a peaceful stay on the edge of the country. Our property has multiple rental buildings, but there is plenty of parking space for anyone traveling with a pickup and trailer.

Top guest favourite
A cozy living area is presented, featuring a stone fireplace with a mounted television above. Comfortable seating options include a leather armchair and a soft couch, arranged around a wooden coffee table. Natural light filters in through the window, enhancing the tranquil environment.
Cabin in Makanda
4.98 out of 5 average rating, 156 reviews

Sanctuary Cabin- Hot Tub & Woods

Hi, hello, welcome! We invite you to take it easy at this unique and tranquil getaway. The kitchen is stocked, the hot tub is ready to go, and the local area boasts many wineries, state parks for hiking, and beautiful scenery. This spacious cabin features a comfortable King bed, 55” TV above a gas fireplace, and recently had a top to bottom renovation! The spacious back deck features a large hot tub just steps from the back door, hooks for the provided terry cloth robes, and a Weber grill.

Top guest favourite
Cabin in Carbondale
4.97 out of 5 average rating, 204 reviews

Romantic Cabin w/ Hot Tub Near Carbondale

The Couple’s Retreat – Secluded Romantic Cabin Near Carbondale, Illinois Designed exclusively for one couple, The Couple’s Retreat is a peaceful hideaway where you can relax, reconnect, and rejuvenate. Enjoy a private hot tub surrounded by trees on a screened porch, cozy evenings by the fireplace, and wildlife views of deer grazing near the firepit. This restful cabin includes a grill, modern amenities, and all the comforts needed for a soothing, intimate Southern Illinois escape.

Top guest favourite
The exterior of the cabin features a welcoming front porch with white railing and potted flowers. Large windows with shutters complement the gray siding, while a central arched window adds character. Lush greenery surrounds the cabin, enhancing its natural setting.
Cottage in Ava
4.95 out of 5 average rating, 118 reviews

Crazy Joe's Cabin #1

Located 2 miles off rt. 151 in Shawnee National forest. The cabin is along tree line just west of Crazy Joe’s Fish House. Restaurant is open at 4pm Wednesday, Friday and Saturday Guests receive $10 food voucher with stay 1bedroom cabin with queen bed, living room with queen sleeper sofa. Full kitchen, bathroom with shower,washer/dryer. Great place for hunting or fishing trip or get away. Smart tvs you can access apps We have 2 other rentals Crazy Joe’s Cabin 2 & Hickey House

Top guest favourite
An inviting modern cabin exterior is illuminated at dusk. The deck features outdoor seating with a table and chairs, complemented by a hot tub nearby. Soft lighting outlines the steps, providing a warm glow against the backdrop of a deep blue sky.
Cabin in Pomona
5 out of 5 average rating, 134 reviews

Modern Cabin at Trillium Ridge

Tucked into the rolling hills of the Shawnee National Forest, our modern cabin offers a welcoming retreat where comfort and nature meet. Wander down a private trail to explore or climb at the Holy Boulders, or take an easy drive to local wineries and see the iconic sights of Little Grand Canyon, Inspiration Point, and Pomona Natural Bridge. When you’re ready to slow down, return to soak in the hot tub, unwind in the sauna, and settle into our cabin made for rest and connection.

Top guest favourite
The treehouse is elevated on wooden stilts, surrounded by lush greenery. A wooden deck with a railing extends from the entrance, creating a welcoming outdoor space. Large windows brighten the upper level, while a sun art piece adorns the side of the structure.
Treehouse in Makanda
4.96 out of 5 average rating, 410 reviews

Panthers Inn Treehouse

Come nestle amongst the leaves at Panthers Inn Treehouse. This secluded, well equipped, elevated cabin has the perfect combination of natural beauty and artful luxury. Isolated yet conveniently located 2 minutes from Blue Sky and Feather Hill wineries, within 5 minutes of Panthers Den hiking trail and the Shawnee Hills canopy tour and only 10 min from I-57 exit 40. Panthers Inn is the perfect starting and ending point to your Shawnee Hills Wine Country vacation!

Top guest favourite
A cozy outdoor seating area is presented with white wicker furniture, including two chairs and a small table, adorned with colorful cushions. Lush green plants are placed around, and a decorative black star is hung on the wall, providing a welcoming touch to the space.
Home in Pinckneyville
5 out of 5 average rating, 20 reviews

Granny’s Getaway

Welcome to Granny’s Getaway, a charming, newly renovated country farmhouse less than 2 miles from town. This peaceful retreat blends rustic charm with modern comfort — perfect for families, couples, hunters, fishermen or small groups looking to relax in a quiet, country setting. We’ve created a space with thoughtful touches and everything you need to settle in & enjoy your stay. The beautiful Pinckneyville City Lake is just a 5 minute walk away.

Top guest favourite
A two-story house with a white exterior and a black roof is seen. The front is adorned with neatly trimmed bushes and a welcoming entrance, featuring a green door and large windows. A clear blue sky provides a bright backdrop.
Home in Pinckneyville
4.95 out of 5 average rating, 262 reviews

The Walnut House

Thank you for checking out The Walnut House. It’s a roomy and comfortable 2 bed 1 bath house in the middle of town. Within walking distance are several restaurants, many local shops, two grocery stores - one with a great deli! The city park has a walking trail, shady picnic areas, a public pool, and tennis and paddleball courts will be completed soon. Come settle in and enjoy a quiet safe small town get-away!

Top guest favourite
Home in Cutler
4.99 out of 5 average rating, 136 reviews

Denmark Roadhouse~A Country Experience

80s farmhouse bordering Pyramid State Park. You and your guests are the only occupants during your stay. You are renting the home. The farm and adjoining areas are rented and there is NO TRESPASSING ALLOWED. Short drive to- Pyramid State Park World Shooting Complex SIU-C DuQuoin State Fairgrounds Shawnee Hills Wine Trail Local Breweries Pyramid Oaks and Red Hawk Golf Courses Kincaid Lake Rend Lake

Superhost
A spacious living area features a light-colored sofa facing a flat-screen television. Natural light streams through large windows with wooden blinds, illuminating the modern kitchen equipped with stainless steel appliances. A dining table surrounded by chairs is positioned nearby on polished wooden flooring.
Flat in Du Quoin
4.88 out of 5 average rating, 110 reviews

30 West·The View·Scenic Escape near Fairground

Step into 30 West · The View, a bright and stylish suite overlooking downtown Du Quoin. Wake up to sunlight streaming through large windows and enjoy being just blocks away from the Fairgrounds, cafés, and shops. Whether you’re here for the State Fair, exploring the wine trail, working remotely, or a quiet getaway, The View offers a light-filled space designed for comfort and convenience.

Top guest favourite
A serene private lake is surrounded by lush trees, reflecting a blue sky. A kayak is on the water, while a small wooden ladder leads to the water's edge. Smooth stones line the shore, creating a peaceful setting for relaxation or water activities.
Cabin in Du Quoin
4.97 out of 5 average rating, 159 reviews

H & B's...Come experience the magic of nature!

The Cabin is nestled in the woods, a few hundred feet from a beautiful private lake. If it's total solitude you are looking for, this is the place. Keyless entry makes it perfect if you want total privacy. If you want lake access, come down and have coffee with us for orientation. Our pantry items, coffee, granola, half & half, and spices are perfect for your full-service kitchen.

Popular amenities for Pinckneyville holiday rentals

  1. Airbnb
  2. United States
  3. Illinois
  4. Perry County
  5. Pinckneyville