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Holiday rentals in Pinckneyville

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Pinckneyville

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Home in Ava
4.93 out of 5 average rating, 139 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
Home in Du Quoin
5 out of 5 average rating, 26 reviews

Sportsman's Oasis

Quiet country setting. Perfect for longer stays with a washer and dryer and all the kitchen amenities. This newly remodeled 3 bed 2 bath home features large bedrooms (king, 2 Queens), large walk-in closets, large kitchen and dining space. Plenty of parking for your trailers. Smart TVs in every bedroom and a 65 inch in the main living room will keep everyone happy. Located 13 miles from Rend Lake, 18 miles from Pyramid State Park and just 2 miles from Duquoin City Lake. 3 miles to DuQuoin.

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, 326 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
The open living area features a comfortable seating arrangement with two sofas and a television mounted on the wall. A stylish dining table is set with round placemats, while large windows allow natural light to fill the space, enhancing the warm, inviting atmosphere.
Barn in Cutler
4.86 out of 5 average rating, 28 reviews

Private, peaceful lakefront home

Enjoy a breathtaking sunrise while you relax on a private lake. This barndominium is fully equipped with modern amenities, while offering a serene experience with access to kayaks & paddle boards, as well as a mile-long hiking trail. While you are tucked away on this private oasis, you are just a short 15 minute drive to local restaurants, and grocery stores. You are also just steps away from beautiful Pyramid State Park. Perfect for couples, small friend groups, small families & pets!

Top guest favourite
A modern kitchen area features sleek white cabinetry and a contrasting black refrigerator. Countertops offer ample space, while a central island with green bar stools invites casual dining. Soft lighting enhances the contemporary design, and exposed brick adds a touch of historic charm.
Flat in Du Quoin
4.98 out of 5 average rating, 57 reviews

Loft Apartment On Main - Sleeps 4

Experience the beauty of downtown Du Quoin at our stunning historic loft apartment. Curated with brand new construction; this space boasts stylish design elements combined with modern amenities to create a truly unique stay. You'll love the large windows, high ceilings, and extra space. This loft boasts a prime location overlooking Main Street. Walking distance: St. Nicholas Hotel Brewery, Biancos ice cream shop, Alongis Italian restaurant, Marks Bakery and many small town shops.

Top guest favourite
The treehouse structure is elevated, supported by stilts, with large windows that reflect the surrounding greenery. The exterior features a combination of wood finishes, and warm lighting casts a welcoming glow in the evening. The pathway leads through the natural landscape to the entrance.
Treehouse in Perryville
5 out of 5 average rating, 702 reviews

Private Treehouse Retreat | Hot tub

The TreeLoft is the first of two treehouses at BaseCamp—designed for cozy seclusion, romance, and rest. Nestled in a private forest just 1 hour from St. Louis, it blends upscale comfort with immersive nature, while still being 20–35 minutes from hiking, wineries, and dining. ✨Our NEW treehouse, The TreeRise, offers an even more elevated, spacious experience at BaseCamp. Perfect for romantic getaways, anniversaries, personal retreats, and intentional escapes to unplug and reconnect.

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, 439 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!

Guest favourite
A duplex structure features a light exterior with black shutters adorning the windows. A covered porch is visible, complemented by a small seating area. The well-maintained yard showcases a clean pathway leading to the front door, with grass extending around the property.
Home in Pinckneyville
4.91 out of 5 average rating, 45 reviews

Duckworth Haven

Welcome to Duckworth Haven in the “friendly little city.” Our 2br- 1 bath property is newly renovated with a fully stocked kitchen and private backyard. We are just blocks away from the fairgrounds and downtown, and we are less than 10 miles from Pyramid State Park. We are a dog friendly airbnb with leads and tennis balls awaiting your furry friends. We have some kid and infant friendly supplies available upon request

Top guest favourite
Home in Cutler
4.99 out of 5 average rating, 140 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
4.98 out of 5 average rating, 45 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.

Superhost
Two elegant wine glasses are placed on a wooden railing, reflecting sunlight. The glasses contain deep red wine, while a lush green field and sparse trees create a serene backdrop in the distance.
Home in Tamaroa
4.87 out of 5 average rating, 93 reviews

The Hideaway

Nature Lovers Paradise-- Disconnect from your devices and connect with nature in this clean, spacious hideaway. If you crave hiking or walking, sitting by the pond, reading on the porch or traveling to nearby wineries and shopping at all the local boutique and antique stores, this is the perfect spot for you to recharge and enjoy. Close to numerous restaurants, and local and state parks.

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, 168 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