Vacation rentals in Charleston

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Top-rated vacation rentals in Charleston

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Top guest favorite
The cabin's welcoming entrance features a wooden porch supported by sturdy beams. Two rocking chairs sit on the porch, surrounded by greenery and stone accents. A red door and a large window enhance the cabin's rustic charm, while the natural setting invites relaxation.
Cabin in Cobden
4.99 out of 5 average rating, 156 reviews

Pop’s Country Cabin

Pop’s Country Cabin is a small remote cabin that sits 1/2mile off the road above a 5 acre lake on 77 acres of private land. The view from the front porch is amazing! You can sit, unwind, and watch the wildlife with a distant view of Bald Knob Cross. The cabin sits in the heart of Shawnee National Forrest and the Southern IL wine trail. You can enjoy the fire pit while watching the stars, with no distractions from neighbors, traffic, or lights. You can enjoy catch & release fishing from the bank

Top guest favorite
A cozy living area features rustic wooden walls and a metal accent wall, with a comfortable seating arrangement on a patterned area rug. A gas fireplace provides warmth, while a smart TV is mounted on the wall, and a dining area is visible in the background.
Home in Golconda
4.93 out of 5 average rating, 132 reviews

Dawns Retreat

No pets. Dawns Retreat is a farm house remodeled in 2023 with a rustic feel that offers a cozy relaxing stay. WiFi 3 smart tv’s 1 Queen 1 full Gas fireplace Gas grill Open fire grill Firewood Electricity at fire pit Plenty of parking Garage Deer hanging station. Heart of Shawnee National Forest. Golconda 10min. Eddyville 15min Harrisburg 35min Paducah KY 35min Note: the field around the yard is private property. Things to do in the area Horseback riding Hiking Boating Fishing Huntin

Top guest favorite
The exterior of a charming house is displayed, featuring a red and white color scheme. A covered porch with a swinging bench is visible, along with a flag pole supporting an American flag. Two windows allow natural light to enter the home.
Bungalow in Karnak
4.99 out of 5 average rating, 135 reviews

Trails End Tunnel Hill Bike Trail Overnight Stay

Located at the end of the 58 mile Tunnel Hill Bike Trail. Fully furnished with full size kitchen, bathroom with shower, bedroom and pool table. No need to pack, all the basic essentials are provided including, but not limited to, bottled water, paper plates, utensils, towels, soap, shampoo, toothpaste, coffee, juice, milk, bread, etc. If it's not there, the Dollar General Store is located 5 blocks away. Full size bed, room for 2 additional people, inflatable mattress available upon request.

Top guest favorite
The interior of the school bus features hand-milled pine finishes, with a cozy couch beside a dining table and chairs. Lighting creates a warm ambiance. The layout includes a kitchen area with basic utensils, while windows provide natural light and views of the surroundings.
Farm stay in Golconda
4.98 out of 5 average rating, 333 reviews

School Bus - Farm Stay Sustainable glamp adventure

This solar powered school bus "Schoolie" tiny home is nestled under open skies, near the forest, with a lake front view, a full bed, kitchen with two burner stove & sink, & a cozy couch. Bliss in the heart of the Shawnee National Forest on Interwoven Permaculture Farm, in Lusk Wilderness. Enjoy star gazing, swimming, and campfires. The chorus of nature will lull you at night, & greet you in the morning. It's a beautiful place to wake up! With kitchen, AC/Heater, this is ultimate glamping!!!

Top guest favorite
The custom-built treehouse is elevated on stilts, surrounded by greenery. A spacious deck features a railing, offering access to the entrance. Steps lead to the ground below, while large glass doors enhance the connection to nature.
Treehouse in Cape Girardeau
4.99 out of 5 average rating, 187 reviews

Twisted Sassafras Treehouse

A custom-built treehouse located on 10 acres with a water view that you can take in from the hot tub on the deck! It is nestled high in the trees and is the perfect romantic getaway for two! Feel like you are away from it all without being away from it all! This treehouse is located on a county road just minutes from Cape Girardeau. Enjoy catch and release fishing on site, local wineries, shopping in historic downtown Cape Girardeau, local restaurants, gambling, historical sites & more!

Top guest favorite
A cozy living space features exposed brick walls complemented by a patterned area rug. Two armchairs provide comfortable seating, one in a checked pattern and the other a textured fabric. A window is adorned with sheer and geometric-patterned curtains, allowing natural light to illuminate the room.
Guesthouse in Cape Girardeau
4.94 out of 5 average rating, 571 reviews

Downtown Guesthouse- Romantic Getaway

The guesthouse seamlessly blends modern amenities with historic charm in a cozy, compact space. The antique claw foot tub/shower combo offers a charming, yet snug, spot for a relaxing soak—true to its historic roots, the bathroom could be best described as a quaint water closet. After a day of exploring unwind in the patio. Play a favorite record, and savor your coffee while daydreaming about new experiences. Despite its small size, it provides all the modern comforts you need.

Top guest favorite
Dome in Stonefort
4.99 out of 5 average rating, 115 reviews

Modern Dome in Shawnee Forest with Hot Tub

Old Colorado Glamping Dome is nestled deep into the woods surrounded by beautiful tall pines. It is heated and cooled and has all the necessities as a typical house. We also packed as many amenities as we could into this property including an oversized 6-Person hot tub, 500 MBPS fiber internet, outdoor tv, fire pit table, Weber grill, hammock swings, custom bathroom with rainfall shower, full kitchen, coffee bar, king & queen sized beds, bean bag toss, board games and much more!

Top guest favorite
A comfortable living area features a stone fireplace beneath a mounted television. A wooden coffee table is surrounded by a brown leather sofa and a chair. Scenic wall art is displayed above the sofa, while natural light enters through a nearby window.
Cabin in Makanda
4.99 out of 5 average rating, 160 reviews

Hygge Log Cabin: HotTub & Hiking

Hi, hello, welcome! We are excited to have the opportunity to host you for your relaxing trip or jam packed adventure. Our local area has many hiking opportunities to explore, the Southern Illinois Wine Trail surrounds us, and the back roads have country views that are breathtaking. Our cabin will be waiting for your arrival or return, well equipped with a 55" TV above the gas fireplace, a comfortable King size bed, and an amazing back porch with a Weber Grill and huge hot tub.

Top guest favorite
The exterior of the cabin is surrounded by tall trees displaying vibrant autumn foliage. A porch extends from the front, offering a view of the yard blanketed in fallen leaves. Sunlight filters through the branches, enhancing the serene woodland setting.
Place to stay in Makanda
4.95 out of 5 average rating, 281 reviews

Secluded Cabin*Blue Sky & Shawnee*Pet-Friendly

Secluded, yet convenient. Within 5 min of two wineries, ziplining, trail heads, & I-57. Your unforgettable romantic wine country retreat or comfortable rest after hiking or travel. No TV or Wi-Fi (good cell signal though) but that is not why you’re here! Explore the vineyards, walk the trails, and drink complementary on-farm roasted coffee! Pets welcome when you add them to the reservation. We have them too! Maple Ridge Cabin : Gateway to Shawnee Wine Country

Top guest favorite
A hand-hewn oak timber cabin is positioned amidst a natural setting, showcasing rustic wooden siding and a welcoming porch. The structure is surrounded by trees and greenery, with steps leading to the entrance, emphasizing a connection to the outdoors.
Cabin in Anna
4.9 out of 5 average rating, 174 reviews

Contemporary Glamping with Native American Appeal!

Luxury Glamping with a taste of Native America! Stay in a hand-hewn oak timber cabin, on the historical "Trail of Tears" in Union County, Illinois. This lodging offers the rustic appeal of an authentic cabin in the woods, with the all the creature comforts and all year around outdoor hot tub. *If you do not find your desired date available, be sure and check our twin cabin listing at AdamsRock Cabins, Cabin #1.

Top guest favorite
A serene cabin sits amidst lush greenery, surrounded by trees that reflect in a tranquil pond. A well-kept lawn leads up to the entrance, enhancing the peaceful setting. Blossoming branches frame the scene, adding a touch of nature’s elegance.
Cabin in Cobden
4.97 out of 5 average rating, 125 reviews

Unique luxury cabin with fireplace and pond view

Shawnee Pond Retreat is a two-bedroom countryside haven that sits on a ridge in the Shawnee National Forest. Located just outside Alto Pass near numerous vineyards, lakes and hiking trails, it is a perfect destination for friends, couples, or families. Shawnee Hills Wine Trail has 11 wineries nearby. With its impressive bluffs and spectacular trailways, Giant City State Park is just a 15-minute drive.

Top guest favorite
A cozy bedroom features a dark brown accent wall, providing a warm backdrop for a spacious wooden bed dressed in crisp white linens. A small seating area with a round table and chairs is positioned nearby, with soft lighting from a stylish chandelier above.
Home in Clinton
4.99 out of 5 average rating, 193 reviews

The Peery House at Springhill Farms

The Peery House is our family home-place, built circa 1900, transformed into a quaint Airbnb. It is located on our farm, Springhill Family Farms in Western KY and is a great place for someone looking to get away from the busyness of life, looking for rest and relaxation or just looking for a unique, little farmhouse while passing through the area.

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