Holiday rentals in Charleston

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Top-rated holiday rentals in Charleston

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

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Top guest favourite
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, 180 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

Guest favourite
Home in Golconda
4.93 out of 5 average rating, 149 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

Guest favourite
A single-story home is presented, featuring a white exterior with black shutters and a welcoming front door. A covered porch with hanging lights is visible, framed by two potted plants. The lawn is well-maintained, surrounded by trees under a clear blue sky.
Tiny home in Bloomfield
4.93 out of 5 average rating, 150 reviews

1-bedroom tiny home located in historic Bloomfield

Kick back and relax in this calm and stylish space located minutes from the Missouri Veterans Cemetery and The Stars and Stripes Muesum and Library. 1bdrm/1bath comfortably sleeps 2 and is furnished with everything you need. Inside you will find all new appliances, bedding, and linens. Circle drive with parking. No smoking or pets allowed. Local restaurants include Las Brasis and Elderland. Or try out locally owned businesses just 6.5 miles drive to Dexter such as Hickory Log and Dexter BBQ!

Top guest favourite
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, 192 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 favourite
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
5 out of 5 average rating, 203 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!

Guest favourite
The front of the cottage is framed by a well-manicured lawn, showcasing a single-story structure with a peaked roof. Two large windows on either side of the double doors provide ample natural light, while two rocking chairs are placed on the covered porch.
Cottage in Bardwell
4.94 out of 5 average rating, 104 reviews

Quiet Country Cottage on Farm-30 Min from Paducah

Charming farm cottage on a hill overlooking West Fork Valley located in rural Carlisle Co. in a peaceful, quiet setting. Our farm has been in our family for 100 years and we love making it available for guests to share our love of the land and the natural beauty of West KY! The cottage features an airy, open floor plan with living, dining sleeping areas & kitchen. There is also one private bedroom & one bath with inviting shower. Woods, creek, wildlife, & only 30 min from Paducah.

Top guest favourite
A modern farmhouse is depicted at sunset, featuring a welcoming entrance with a covered porch. A stone pathway leads to the front door, bordered by a grassy lawn that extends to fields and trees in the background.
Barn in Cape Girardeau
4.95 out of 5 average rating, 261 reviews

Under the Stars - Farmhouse

Enjoy the tranquility of this modern farmhouse charmer! Custom built minutes from downtown Cape. Relax outside around the fire pit, roast marshmallows and watch the sunset. Finish the night with a long soak in the hot tub. Start the morning on the front porch rocking chairs and take in a sunrise. Open concept, fully equipped kitchen, 3 Bd. including King master/full bath, 2 Queens with full guest bath. Near Trail of Tears and walking distance to classic dive bar/burger joint

Top guest favourite
A living area features exposed brick walls and large windows allowing natural light. A comfortable blue couch and a smaller chair are arranged around a wooden coffee table, which is adorned with decorative items. A ceiling fan and shelving add functional touches to the cozy space.
Apartment in Paducah
4.95 out of 5 average rating, 707 reviews

Cozy studio in The Foxbriar - Downtown

Home of the former Foxbriar Inn, this condo is located inside a beautiful historic building. This space is great for your weekend away or a longer term stay. Exposed brick and high ceilings make it a charming and cozy experience. Enjoy the perks of walking to lots of great restaurants, specialty shopping and boutiques. We are just seconds from a beautiful stroll along the River. Bakery and coffee shop underneath. Enjoy brunch on the weekends or a sweet treat anytime in the week.

Guest favourite
A wooden deck lined with rustic rocking chairs offers a serene view of the surrounding forest. The lush greenery creates a peaceful backdrop, inviting relaxation and enjoyment of nature.
Cabin in Pope County
4.92 out of 5 average rating, 346 reviews

Beck's Hideaway at Dixon Springs

We might call this place a hideaway but the nearby activities and amenities are too numerous to list! Enjoy the secluded forest location surrounded by towering trees, abundant wildlife, and plenty of outdoor activities. Our cabin is just minutes away from the Trail of Tears, Dixon Springs State Park, the delicious Chocolate Factory, the towns of Golconda, Metropolis, and the bigger city of Paducah. NEW IN OCTOBER 2021: We have installed high-speed fiber optic WiFi to the cabin.

Top guest favourite
Cabin in Paris
4.99 out of 5 average rating, 283 reviews

Pops Cabin

Conveniently located approx 5 miles west of Paris. Pops Cabin, is located on our small 16 acre (work in progress) hobby farm of goats, chickens, 2 farm friendly dogs and occasionally a cat or 2 can be observed. :) You get the cabin all to yourself and It comes with 3 bedrooms, 3.5 baths, full kitchen, a front porch to sit down and relax. Yard space available for children to play in. We are a working farm, pets are allowed under certain conditions, along with a 40 pet fee.

Guest favourite
A covered porch offers expansive views of rolling hills and a glistening pond. A swing chair is positioned to the side, inviting relaxation, while flower beds with vibrant blooms border the entrance. Sunlight illuminates the landscape, enhancing the natural beauty of the surroundings.
Cabin in Fredericktown
4.97 out of 5 average rating, 335 reviews

Cabin on the farm

The Space Rustic charm meets the serene beauty of the Ozarks in this magical setting overlooking our farm, offering a perfect retreat for rest or a base camp for your next adventure. Inside, you'll find a cozy living space decorated with modern farmhouse charm, complete with a warm electric fireplace. Relax in the comfortable king-size bedroom after a day of exploring. The cottage also includes a well-appointed bathroom and a functional kitchenette for your convenience.

Top guest favourite
A rustic cottage is nestled among tall trees, showcasing a natural setting during autumn. Colorful fall foliage blends with the greenery, while fallen leaves cover the ground. The warm tones of the cottage complement the serene landscape.
Place to stay in Cobden
4.95 out of 5 average rating, 335 reviews

Eva’s Roost - Center For Lost Arts

Eva’s Roost is located at Center For Lost Arts near Cobden, Illinois. Uniquely crafted rustic, zen-style cottage, designed to be close to the earth & nature. Extensive, curtainless windows facing the forest & pond allow for private views: sunrise, moonrise, forest & wildlife. Yoga mat, guitar & some art supplies. Personal outdoor space with firepit & comfy adirondack chairs. Entrance to wandering trails right outside your back door. Perfect place to retreat and renew.

Popular amenities for Charleston holiday rentals