Holiday houses in Charleston

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Top-rated holiday rentals in Charleston

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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, 145 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
An exterior view of the entrance features a welcoming white door framed by black accents. A small staircase leads up to the door, complemented by a light fixture. A vehicle is parked near the entrance, with a tree and a fenced area visible in the background.
Guest suite in Cape Girardeau
4.98 out of 5 average rating, 167 reviews

MAINSTAY CAPE [downtown]

Nestled in the heart of the Downtown Historic District, this suite is centrally located as a prime destination for any and all travelers alike. With parking available, this space offers a unique & trendy “midwest boho” vibe. ~WALKABLE~ Our studio is 1 block from the bustling Southeast Missouri State University, 1 block from the gorgeous Capaha Park, and 2 blocks from Mercy Hospital. If you are interested in night life, this space is simply a 5-10 minute walk to all DT bars and restaurants.

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, 119 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
4.99 out of 5 average rating, 168 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
A dining area features a wooden table surrounded by six black chairs. A decorative bowl filled with oranges sits at the center. Soft light is provided by an elegant hanging fixture above, and a softly lit sleeping area is visible in the background.
Cottage in Paducah
4.91 out of 5 average rating, 380 reviews

Commonwealth Cottage

Constructed in 2020! Commonwealth Cottage is an modern, cozy getaway in Paducah on site of the Commonwealth Event Center. Enjoy the 16 acre grounds with a panoramic pond view while being located a mile from Paducah’s main hub. Enjoy ample indoor space for up to 8 guests to stay & a back porch to enjoy the view. The main room includes a king bed, mini fridge and microwave, dining table, & living room with a sleeper sofa. An additional bedroom includes a full bed with twin bunk & trundle.

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.
Guesthouse in Cape Girardeau
4.94 out of 5 average rating, 548 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 favourite
The spacious living room features soft beige carpeting, a coffee table with decorative elements, and two comfortable armchairs. A large window offers natural light, while a star-shaped decor piece adds visual interest to the neutral-colored walls. A doorway leads to the kitchenette.
Apartment in Paducah
4.97 out of 5 average rating, 115 reviews

Dee’s Downstairs Private Apartment

1 bedroom with a Queen size bed and a twin rollaway bed. This space is a private apartment in the basement of my home with separate entrance. Sole access to the living room, 1 bedroom with queen bed, full bathroom, game area with foosball and ping pong tables, and kitchenette. Located on 1 acre, so it’s private, but still in town. 5 miles to downtown and 3 miles to mall area. Screened in porch and fire pit area might be shared during summer months.

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
4.92 out of 5 average rating, 279 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.

Guest favourite
A cozy living room is presented, featuring a comfortable sofa with colorful cushions and a wooden coffee table at its center. A flat-screen TV is positioned against the wall, with a recliner and chair nearby. Light streams through the window, illuminating the warm tones of the space.
Home in Union City
4.95 out of 5 average rating, 346 reviews

Gloria’s on Exchange-Entire Home-3rd bedroom opt

Welcome to Gloria’s on Exchange, a cozy home away from home located in a quiet historic neighborhood. The bones of our home date to 1910, but this little house has received a loving renovation. Local art gives off a “rustic” feel, but all is completely tricked out with smart technology and very cozy furniture and bedding. 2 BEDROOMS/2 BATHS ARE INCLUDED IN THE LISTED PRICE. ADD ON OPTION for 3rd bedroom access w queen bed for $30 per night.

Top Guest favourite
An industrial-style kitchen features exposed brick walls and a stainless steel backsplash. A central island with two stools offers a casual dining space. Modern appliances, including a large refrigerator and a professional-grade stove, are integrated into the design, complemented by warm wooden flooring.
Condo in Paducah
5 out of 5 average rating, 218 reviews

Luxury 2 BR 2 Bath Downtown Double Condo

This luxury 2 bed 2 bath 1900 square foot double condo is centrally located in downtown Paducah across the street from Maiden Alley, the Carson Center, and the Market House Theater. Built in 1870, “The Parlour” is a historic property that has been renovated with modern touches while preserving yesterday’s charm. Guests can walk to many local attractions and Paducah’s best bars, shops, and restaurants.

Top Guest favourite
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, 186 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
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, 624 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.

Popular amenities for Charleston holiday rentals