Vacation rentals in Whittington

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Top-rated vacation rentals in Whittington

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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, 250 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

A renovated house is set amidst a lush green yard, featuring light blue siding and a welcoming front porch with white railings. A wooden deck is visible at the back, surrounded by trees, creating a peaceful atmosphere.

Home in Benton

4.93 out of 5 average rating, 27 reviews

The Anderson House

Experience the charm of Southern Illinois in the peaceful comfort of The Anderson House, a newly renovated 2-bed, 2-bath home with roots dating back to 1932. Featuring a full kitchen, an open floor plan, and inviting outdoor spaces, The Anderson House offers a perfect retreat for relaxation or exploration. A short walk across the grounds leads to a small coffee roastery, farmland, and a state forestry park, where guests can immerse themselves in outdoor activities or enjoy a delicious coffee.

Top guest favorite

A modern dome structure features large glass panels creating a bright and inviting environment. Surrounded by lush greenery, the architecture harmonizes with nature. A wooden deck with seating is visible in front, offering a space for relaxation and outdoor enjoyment.

Dome in Cobden

5 out of 5 average rating, 103 reviews

The Dome At Blueberry Hill

Escape to The Dome at Blueberry Hill, where comfort meets nature for a truly unforgettable glamping experience. Set on two private acres along the scenic Shawnee Hills Wine Trail and minutes from the charming village of Cobden- you’ll enjoy peaceful seclusion with easy access to local charm. The fully insulated dome offers cozy, climate-controlled comfort year-round. Sip wine under the stars or unwind in style indoors. Make lasting memories at The Dome- your luxury glamping retreat awaits.

Top guest favorite

An open interior features a cozy seating area with a dark leather chair and a spacious bed dressed in soft linens. Natural light enters through two windows, while wooden beams and a sloped ceiling add warmth to the space. A kitchenette is visible in the background.

Tiny home in Whittington

4.93 out of 5 average rating, 165 reviews

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.

Top guest favorite

A rustic cabin is highlighted with wooden siding and a welcoming front porch. Comfortable seating is arranged on the porch, and the warm glow of exterior lighting enhances the evening atmosphere. Views of the nearby pond and surrounding trees are visible from the porch.

Tiny home in Ewing

5 out of 5 average rating, 174 reviews

LilyPad-pondside cabin, kayaks, trail, country

Great for a couple, an outdoorsman, or travelers! This cabin is located on our 20 acre property, less than 10 minutes from Rend Lake, I57 access, and public hunting land and within 1 hour of the Shawnee National Forest. Includes use of kayaks, fishing poles for the catch & release pond, and a walking trail. Bow target use available upon request. Gas grill, firepit and firewood. PLEASE NOTE: its a 12x20 studio cabin with 1 full bed and 1 twin sized foam couch sleeper. We don't allow pets.

Guest favorite

A cozy sitting area is surrounded by wooden walls, featuring a large window that offers views of the forest. A red chair stands next to a small side table, while a gray couch is positioned against the wall. Decorative art pieces adorn the space.

Tiny home in Cobden

4.95 out of 5 average rating, 114 reviews

Tiny House of Paul - Center For Lost Arts

Perfect if you're working or spending time exploring Southern Illinois. Great discount for longer stays. Tiny House of Paul house has a cozy & spacious feel. A large west-facing window looks out onto the forest. Windows in the loft open to tree tops & stars. Private inside. Centrally located on the property of Center For Lost Arts near Cobden, Illinois. Wander the trails at the end of a work day, or relax on the deck after hiking or exploring. Enjoy your time in Southernmost Illinois.

Guest favorite

The exterior of the home is visible, set within a spacious green yard. A garage is positioned to one side, with a driveway leading up to the entrance. Surrounding trees provide a natural backdrop, enhancing the serene country setting.

Home in Ewing

4.9 out of 5 average rating, 127 reviews

"Quiet And Secluded Country Setting" BIG OAKS

We have a 2000 sq. ft. home located on 3 acres in a very country setting. It has 3 bedrooms, 2 baths, master bed room has queen size bed, second bedroom has full size bed and third bedroom has 2 twin beds. Large master bath with large soaking tub and shower. Spacious kitchen is set up to cook if you like, . The back porch over looks the woods and fields with lots of deer siting. Our location is very quit and peaceful. also there is a garage you have access to.

Top 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, 130 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

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

4.98 out of 5 average rating, 149 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

The spacious interior features a wood-beamed ceiling with natural light streaming through large windows. A comfortable leather sofa is positioned next to a sleek kitchen with modern appliances, while a dining counter with bar stools offers additional seating.

Tiny home in Marion

4.97 out of 5 average rating, 176 reviews

Pet-Friendly Waterfront Studio Cabin

Step inside to an open, airy living space with vaulted wood ceilings and sunlight pouring through the windows. The cabin features a fully-equipped kitchen, a modern bathroom with a washer and dryer, and a cozy living area with a Smart TV. Just outside, a large covered deck overlooks a serene, fishable, swimmable pond, offering beautiful water views right from your door.

Guest favorite

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

4.93 out of 5 average rating, 126 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.