Vacation rentals in Pinckneyville

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Top-rated vacation rentals in Pinckneyville

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

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Top guest favorite
The charming bungalow features a covered porch with yellow accents and green trim. Lush greenery surrounds the space, highlighted by colorful flower beds. A stone pathway leads up to the entrance, inviting guests into a warm and welcoming atmosphere.
Home in Carbondale
5 out of 5 average rating, 629 reviews

Charming 3 bedroom bungalow in Downtown Carbondale

Originally built in 1920, this cute bungalow house has been totally renovated and modernized. You'll enjoy 3 furnished bedrooms, 1 bathroom, covered porch, and back with lighted pergola and firepit. The location is exceptional - just two blocks North of the Carbondale downtown "strip," and EASILY walkable to all the downtown businesses, Memorial Hospital of Carbondale (0.4 miles), restaurants, pubs, Amtrak station (0.5 miles), and SIU (about 1.2 miles). Officially Permitted Airbnb VRU 23-03

Top guest favorite
A cabin with wooden exterior is surrounded by tall trees and shaded ground. A spacious porch is visible at the front entrance. A calm dog sits on the ground in the foreground, offering a glimpse of the natural tranquility of the setting.
Cabin in Alto Pass
4.99 out of 5 average rating, 305 reviews

Ma's Cabin, Alto Pass, IL. Fine country lodging.

Cute and country remodel done in 2019. Recent new appliances, furnishings, flooring, heat & A/C, washer & dryer. Cabin is secluded and quiet plus 1/2 mile from Alto Pass Lookout Point and right in the middle of many award-winning wineries. 15 miles from Carbondale 4 miles from Giant City 30 miles from Garden of the Gods 6 lakes within 10-mile radius Hundreds of miles of hiking trails in nearby Shawnee National Forest 6 miles from Bald Knob Cross Please, no dogs! No smoking in cabin!

Top guest favorite
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, 273 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 favorite
Tiny home in Whittington
4.91 out of 5 average rating, 298 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 favorite
Home in Pinckneyville
5 out of 5 average rating, 16 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.

Guest favorite
A well-maintained front yard features two small trees with green foliage, providing a sense of tranquility. The house, characterized by white siding, has multiple windows that allow natural light to illuminate the interior. A concrete pathway leads to the entrance, enhancing accessibility.
Home in Sesser
4.95 out of 5 average rating, 132 reviews

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.

Top guest favorite
Home in Pinckneyville
4.95 out of 5 average rating, 260 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!

Guest favorite
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
4.92 out of 5 average rating, 39 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 favorite
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 favorite
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 favorite
A spacious screened porch is highlighted by large windows on three sides, allowing natural light to fill the interior. The porch is surrounded by a verdant lawn and mature trees, creating a serene outdoor environment. Visible walls feature wooden paneling and earthy tones.
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.

Guest favorite
A charming cottage is framed by tall grasses, with vibrant fall foliage surrounding it. The exterior features white siding and a green metal roof, while a welcoming porch is visible at the front entrance. The landscape offers an expansive view of the serene countryside.
Cottage in Pinckneyville
4.84 out of 5 average rating, 80 reviews

Cozy cottage in peaceful setting.

Unwind and relax in this cozy cottage in Pinckneyville, Illinois! Enjoy serene farmland views, grill out or go into town and eat out! Keep your eye out for the deer that reside on the property or look for bald eagles! This cottage is five minutes from town, a few minutes from Pyramid State Park and thirty minutes from the World Shooting Complex in Sparta, Illinois.

Popular amenities for Pinckneyville vacation rentals

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