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
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, 323 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 favourite
A red barn with a peaked roof is set against a lush green landscape, reflecting softly in a calm pond nearby. Tall grasses frame the water’s edge, while trees provide a natural backdrop under a partly cloudy sky.
Cabin in Dongola
5 out of 5 average rating, 103 reviews

Charming Cabin Overlooking 5 Acre Lake

This cozy, newly remodeled, and inviting cabin offers you a relaxing, serene, and tranquil setting. During your stay you will see nature at its finest. Enjoy a drink on the large deck overlooking the picturesque landscape as well as the lake. If you enjoy fishing then this stocked lake is the place for you. Feel free to fish on the bank or the dock. This cabin is part of the original homestead that was established in 1855 by Valentine Kimber. Located close to wine trails and interstate 57.

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, 208 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, 105 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
4.94 out of 5 average rating, 269 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

Guest favourite
A modern tiny home features a welcoming entrance, with a wooden porch and steps leading up to the front door. Rocking chairs provide a cozy seating area, surrounded by a gravel pathway and green lawn. Trees are seen in the background, adding to the serene setting.
Tiny home in Bardwell
4.93 out of 5 average rating, 55 reviews

The Roost - Pets friendly

Welcome to The Roost, a cozy, modern tiny home in rural western Kentucky. With two lofts, a bedroom, full kitchen, washer/dryer, and space to sleep five, it’s perfect for a peaceful getaway. The property is home to our 4 off leash dogs who will greet you upon arrival. We ask all other animals are dog friendly. Enjoy sunsets, stocked ponds, wildlife, outdoor dining, and a fire pit. Named after The Hickory Chicken—Southern slang for morel mushrooms—this hidden gem is worth the search

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, 338 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.

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, 443 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!

Top guest favourite
A cozy living room is showcased with a gray sofa adorned with decorative pillows, flanked by two red armchairs. A wooden coffee table sits in the center, holding a glass bowl and remote control. A rug adds texture, while natural light filters through a sheer curtain.
Home in Sikeston
5 out of 5 average rating, 29 reviews

Emma’s Cottage

Take it easy at this unique and tranquil getaway. Emma’s cottage is located in the historic north end of Sikeston, just minutes away from the local hospital and power plant, which makes it a perfect place for traveling professionals and people coming into town to visit friends and family. This cottage is 2 bedrooms, 1 bathroom, with a queen bed and a full bed.

Top guest favourite
Home in Clinton
4.99 out of 5 average rating, 204 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.

Top guest favourite
Home in Hornbeak
4.99 out of 5 average rating, 153 reviews

THE DREAMCATCHER

Beautiful brick home with lake view and access to Reelfoot Lake (no ramp), paved drive with ample parking for boat / trailer, back deck with table and chairs, open space kitchen and den, perfect for group fishing trip, hunting trip, or just sight seeing, (area known for its large population of eagles), quiet neighborhood, peaceful place to stay.

Top guest favourite
A comfortable living area features a dark sofa adorned with a seasonal pillow. A round chandelier hangs above, providing soft lighting. A coffee table rests in front of the couch, surrounded by side tables with lamps. Wall art depicting winter scenes is displayed above the sofa.
Cottage in Paducah
4.99 out of 5 average rating, 703 reviews

Copper Creek Cottage in the country close to city

Welcome to Copper Creek Cottage. We are located in the country but minutes away from downtown Paducah, and the mall area. We are 2.5 miles from I-24. Our cottage sleeps 4. (Queen bed & full pull-out sofa). The cottage is great for a couple's weekend, girls' trip or any occasion. The nightly price will be reduced for longer stays.

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