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Holiday rentals in Charleston

Find and book unique accommodation on Airbnb

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 spacious living area features large windows allowing natural light to fill the space. A comfortable grey sofa is paired with a unique coffee table, while stylish dining chairs surround a white table. The kitchen area includes modern appliances and cabinetry.
Flat in Cape Girardeau
4.95 out of 5 average rating, 319 reviews

Brand new 2 bedroom unit right in downtown Cape.

This special place is close to everything, making it easy to plan your visit. Walking distance to restaurants, the river and nightlife. Property includes wifi, full kitchen, laundry, deck and private parking for one. One king bed room and a twin bed room in addition to a roll out twin bed along with a 60 inch smart television. Dog bed and bowls included along with board games! Property is conveniently located across the street from "The Bar" the famous spot from the movie "Gone Girl" .

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
5.0 out of 5 average rating, 214 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, 107 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.

Superhost
A cozy living area features a white fireplace with a wooden mantel. A television sits atop the mantel, framed by a floral arrangement. A patterned armchair is positioned nearby, complementing the neutral tones of the walls and flooring.
Home in Kevil
5.0 out of 5 average rating, 100 reviews

Hosta House

Enjoy an adult stay in this private cozy getaway. This entire space is single level, quiet and just minutes from Paducah. (Outdoor kenneling accepted no indoor pets.) The country setting is ideal for a quiet weekend or longer stay. The private patio is a perfect place to have your morning coffee and evening wine while enjoying the flowers and sunsets. You will enjoy the roomy space and French touches no matter the reason for your visit. Summer grounds boast over 100 hosta varieties.

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, 280 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 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.
Guest house in Cape Girardeau
4.94 out of 5 average rating, 607 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.

Superhost
The exterior of a newly renovated home is showcased, featuring a brown brick façade, a welcoming front porch with seating, and decorative flower pots. A well-kept lawn leads to a gravel driveway that provides access to the entrance.
Home in Sikeston
4.97 out of 5 average rating, 29 reviews

Newly Renovated 3 Bedroom 2 Bath Home - Sleeps 9

Looking for a spacious and welcoming Airbnb in Sikeston? 🏡✨ This gorgeous, newly renovated 3 bedroom, 2 bathroom home is the ideal destination for unforgettable memories with your loved ones. The house sleeps up to 9 guests comfortably, making it perfect for families and groups. Conveniently located in a fantastic residential area, you're just moments away from local attractions, shopping, and dining spots.

Guest favourite
The two-story brick home is surrounded by lush green grass and large trees, offering a spacious front yard. A welcoming entrance with a white frame and several windows enhances the inviting appearance of the house, which is partially fenced and set against a backdrop of nature.
Home in Cape Girardeau
4.98 out of 5 average rating, 454 reviews

The Hamilton House

Majestic, Two Story Home. A Great Place for Making Memories. BEFORE YOU BOOK: So there are no misunderstandings. Please read our rules, and understand our pricing, because there is an extra guest fee after the first 2 guests and weekends are priced different than weekdays. 2 Night Min. Stay on Weekends Only - 1 Night Stays Sun. - Thurs. No Parties-No Smoking-No Animals

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
5.0 out of 5 average rating, 32 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, 210 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.

Superhost
Home in Wickliffe
4.91 out of 5 average rating, 45 reviews

Large living space, 4 bedroom, outdoor fire pit

Spacious 4BR/2BA cabin in Wickliffe, KY—ideal for work crews, hunters, or families. Sleeps 8 with full kitchen, washer/dryer, and cozy living space. Plenty of parking for trucks and trailers. Quiet, rural setting close to Kentucky Lake, hunting, fishing, paper mill, river industry and KY/IL bridge project.

Superhost
Home in Bloomfield
4.96 out of 5 average rating, 203 reviews

Bloomfield Bungalow

Bloomfield Bungalow is new construction that boasts a cathedral ceiling upon entry with a spacious open concept. It has everything you'll need to kickback and fully relax. This two-bedroom, two-bath home offers a fully equipped kitchen, workspace, and large sofa for lounging.

Popular amenities for Charleston holiday rentals