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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, 163 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 favourite
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, 141 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 favourite
A circular patio made of stone pavers is set in front of a red cabin. Two black Adirondack chairs are positioned around a fire pit, surrounded by fallen leaves and trees with autumn foliage. The cabin features a welcoming door and flower pots by the windows.
Cabin in Alto Pass
5 out of 5 average rating, 136 reviews

Bald Knob Cabin

Located in heart of Shawnee National Forest, Bald Knob Wilderness and River To River Trail , is a former orchard turned cozy hiker/biker haven. Just 2 miles down the road from Bald Knob Cross of Peace. This studio style cabin was recently renovated and has a fully functioning kitchen. Bald Knob Cabin is the ideal location to unplug and put your feet up after a long day hiking trails or traveling the Shawnee Wine Trail that flows through the cozy, inviting town of Alto Pass. No WIFI or TV!

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
4.99 out of 5 average rating, 192 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 favourite
A cozy living area is presented, featuring a stone fireplace with a mounted television above. Comfortable seating options include a leather armchair and a soft couch, arranged around a wooden coffee table. Natural light filters in through the window, enhancing the tranquil environment.
Cabin in Makanda
4.98 out of 5 average rating, 157 reviews

Sanctuary Cabin- Hot Tub & Woods

Hi, hello, welcome! We invite you to take it easy at this unique and tranquil getaway. The kitchen is stocked, the hot tub is ready to go, and the local area boasts many wineries, state parks for hiking, and beautiful scenery. This spacious cabin features a comfortable King bed, 55” TV above a gas fireplace, and recently had a top to bottom renovation! The spacious back deck features a large hot tub just steps from the back door, hooks for the provided terry cloth robes, and a Weber grill.

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, 102 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 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, 127 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.

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
4.94 out of 5 average rating, 249 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
Dome in Stonefort
4.99 out of 5 average rating, 124 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 favourite
A spacious sleeping area is showcased with a textured blanket draping over the bed. In the background, cozy seating includes two armchairs positioned near a small table, with a decorative shelving unit filled with books. Large windows enhance natural light throughout the space.
Treehouse in Perryville
4.95 out of 5 average rating, 186 reviews

Rustic reTREEt Treehouse Getaway

This treehouse features a gorgeous floor-to-ceiling stone indoor/outdoor fireplace, vaulted ceiling, and many large windows which provide natural light and beautiful views. The interior design fuses natural elements of wood and stone, with a more refined and polished urban country look. A partition wall creates intimate spaces w/in this large (950 sq.ft.) open floor plan. Highlights: king size bed, corner claw tub, rainfall shower, reading area, 65" TV, large deck, & BBQ grill.

Top guest favourite
The treehouse is elevated on wooden stilts, surrounded by lush greenery. A wooden deck with a railing extends from the entrance, creating a welcoming outdoor space. Large windows brighten the upper level, while a sun art piece adorns the side of the structure.
Treehouse in Makanda
4.96 out of 5 average rating, 414 reviews

Panthers Inn Treehouse

Come nestle amongst the leaves at Panthers Inn Treehouse. This secluded, well equipped, elevated cabin has the perfect combination of natural beauty and artful luxury. Isolated yet conveniently located 2 minutes from Blue Sky and Feather Hill wineries, within 5 minutes of Panthers Den hiking trail and the Shawnee Hills canopy tour and only 10 min from I-57 exit 40. Panthers Inn is the perfect starting and ending point to your Shawnee Hills Wine Country vacation!

Guest favourite
A new hot tub is prominently featured on a wooden deck, surrounded by rustic red fencing. Chairs and a table are set nearby, creating a welcoming outdoor space. Lush greenery and trees provide a natural backdrop, enhancing the cabin's serene atmosphere.
Cabin in Cape Girardeau
4.91 out of 5 average rating, 300 reviews

Log Cabin w/ Hot tub - Near Casino & Downtown Cape

THE BEST GETAWAY HERE IN CAPE! Have a relaxing staycation here in Cape Girardeau Perfect for a QUICK GETAWAY for couples, families or friends 5 MINS to the casino, country club and downtown cape Very unique log home with a private bedroom queen size bed, pull-out queen size futon in the living room and twin size hide away SLEEPS 4. Pool table, darts, and a hot tub.There is a large deck and fire pit which has the feel of being in the woods.

Popular amenities for Charleston holiday rentals