Holiday houses 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, 128 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.

Top Guest favourite
The exterior of a charming cottage features a welcoming entrance with a light-colored door. Two blue chairs and a small table are positioned on a stone path, surrounded by well-maintained grass and flower pots. In the background, horses can be seen grazing in a fenced pasture.
Guesthouse in Carbondale
5 out of 5 average rating, 268 reviews

Homestead Cottage

Enjoy tiny farmhouse life in this adorable 375 sq. foot cottage. Loaded with everything you need this little cottage is nestled privately behind some trees on our 11 acre farm. You will soon forget how close you are to town with the beautiful view from your windows and the pasture fence just steps out the back door. Whether you’re here for the wineries, amazing hiking, an SIU event (3 miles) or to visit with family, the Homestead Cottage will provide a comfortable retreat from any adventure.

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, 295 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.

Guest favourite
A gravel pathway is bordered by lush greenery and natural stone slabs. The route leads through a landscaped area featuring shrubs and trees, contributing to a serene and inviting outdoor environment.
Home in Marion
4.8 out of 5 average rating, 766 reviews

Frank Lloyd Wright design inspired house

PET FRIENDLY-Frank Lloyd Wright design. This home is Unique and spacious! It is conveniently located near interstate 57, and 12 minutes from the Lake of Egypt. It is also close to Shawnee Hills National Forest for beautiful hiking trails and picnics as well as 12 local wineries! After your adventures, Relax in the rustic outdoor area that provides plenty of privacy. Or in the theatre room that has a large tv and recliners to watch your favorite movies or cheer on your favorite team!

Top Guest favourite
Cabin in Carbondale
4.97 out of 5 average rating, 183 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, 116 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
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, 255 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
The exterior of a charming farmhouse is displayed, featuring a red metal roof and a combination of light and dark siding. A covered porch area includes multiple black chairs. A garage is visible to the right, with gravel providing access to the entrance.
Home in Cutler
4.98 out of 5 average rating, 133 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

Top Guest favourite
A single-story house is set on a green lawn, featuring a light exterior with blue shutters. A concrete walkway leads to the entrance, framed by neatly trimmed shrubs. Tall trees provide a natural backdrop, contributing to a peaceful setting.
Cottage in Pinckneyville
4.97 out of 5 average rating, 29 reviews

Lake Road Cottage

Peaceful family retreat just a short walk to the city lake and boat dock. Perfect for anyone seeking a quiet escape. Enjoy boating, kayaking, fishing, or a lakeside picnic, then relax on the covered deck, fire up the patio grill, or get cozy around the fire pit while watching the sunset. Start your mornings at the stocked coffee bar, and take advantage of the on-site washer/dryer for added 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, 155 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.

Superhost
A modern kitchen area features stainless steel appliances against exposed brick walls, creating a warm ambiance. A wooden island with two stools centers the space, while cabinetry provides storage. Natural light illuminates the area, highlighting the blend of rustic and contemporary elements.
Apartment in Du Quoin
4.91 out of 5 average rating, 134 reviews

30 West·The Den ·Downtown Hideaway near Fairground

Welcome to 30 West · The Den, a modern downtown hideaway in the heart of Du Quoin. Just minutes from the State Fairgrounds, local restaurants, and the Shawnee Wine Trail, this cozy retreat is perfect for couples, solo travelers, or remote workers. With thoughtful touches, fast Wi-Fi, and a warm atmosphere, you’ll feel right at home.

Top Guest favourite
A cozy living area features a navy blue sofa adorned with Union Jack pillows, complemented by a round wooden coffee table. Two windows allow natural light to brighten the space, while light curtains filter the view. A decorative lamp and side table add functionality.
Loft in Pinckneyville
5 out of 5 average rating, 105 reviews

The London Loft

NEWLY RENOVATED! Enjoy a stylish experience at this centrally-located loft right in the heart of Pinckneyville with 1 bedroom, 1 king bed, 1 rollaway cot and one futon. You will be literal steps away from almost everything Pinckneyville has to offer. Come visit the Friendly Little City! You’ll be glad you did!

Popular amenities for Pinckneyville holiday rentals

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