Vacation rentals in Pinckneyville

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.

Tiny Cottage 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.

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

Hunting, fishing, golf & beaches!

Welcoming family-style 2 bedroom home. Full kitchen/dining room/living room. Home boasts wood paneling and a 1940's vibe. Updated home of 4 generations. Full functioning kitchen with large refrigerator, stove, microwave and coffee maker. Laundry off the dining area, private driveway, back yard has charcoal grill & firepit. Beautiful, quiet neighborhood close to Rend Lake. Hunting, fishing, golfing, beaches within 5 miles.

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!

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

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.

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.

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!