Vacation rentals in Charleston

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Top-rated vacation rentals in Charleston

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

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Top guest favorite
A rustic cabin is viewed from the front porch, featuring two rocking chairs positioned to face the surroundings. Soft warm lights illuminate the porch, while greenery is visible in planters. The exterior showcases wooden siding and a welcoming red door, surrounded by a gravel pathway.
Cabin in Cobden
4.99 out of 5 average rating, 174 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 favorite
The geodesic dome is positioned among tall trees, illuminated by the glow of a fire pit in the foreground. A staircase leads up to the entrance, under a darkening sky with early stars becoming visible.
Dome in Perryville
4.94 out of 5 average rating, 167 reviews

The Snow Globe*OffGrid DomeGLAMP*Adventurers Only

EXPERIENCE The Dome in the Woods • IMMERSE in complete silence with the absence of electricity: no hum or vibrations from this completely solar/propane fueled geodesic dome. NoAC • GLAMP in this OFF GRID ADVENTURE. 430 sq ft floor plan. 14 ft ceiling. 20 ft bay window with endless nature view at the foot of your bed. Lofted 7ft. • STARGAZE from the deck or fire pit • NESTLE in the romantic wooded nature of southeast MO. S of St Louis.N of Memphis • UNPLUG, UNWIND, RELAX. Adventure seekers only!

Top guest favorite
Cabin in Pomona
4.96 out of 5 average rating, 237 reviews

Artist Vibe on the SI Wine Trail. New Kitchen!

What makes The Loft truly unique is its location. At the start of the S.I. Wine Trail, the cabin is just minutes to Cedar Lake, 15 minutes from nationally award winning BBQ, delicious ice cream, shopping, and fun of all sorts! On a 70 acre organic farm, the cabin is tucked into a breathtaking valley next to the Shawnee National Forest and has a gourmet kitchen and is filled with antiques, games & play space, original eclectic artwork, plus toddler gear so you can travel light! You’ll love it!

Top guest favorite
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, 198 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 favorite
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 favorite
A cozy outdoor fire pit area is surrounded by five blue Adirondack chairs, set against a vibrant sunset sky. Warm lighting hangs overhead, illuminating the spacious yard and providing a welcoming atmosphere for evening gatherings.
Barn in Cape Girardeau
4.95 out of 5 average rating, 256 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 favorite
Guesthouse in Cape Girardeau
4.94 out of 5 average rating, 587 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 favorite
A modern hot tub is positioned on a wooden deck, featuring illuminated water that reflects a soothing blue hue. Nearby, a dining area is displayed with a vibrant table and colorful chairs, framed by blooming flowers and the warm glow of the cabin's windows.
Cabin in Pomona
5 out of 5 average rating, 145 reviews

Modern Cabin at Trillium Ridge

Tucked into the rolling hills of the Shawnee National Forest, our modern cabin offers a welcoming retreat where comfort and nature meet. Wander down a private trail to explore or climb at the Holy Boulders, or take an easy drive to local wineries and see the iconic sights of Little Grand Canyon, Inspiration Point, and Pomona Natural Bridge. When you’re ready to slow down, return to soak in the hot tub, unwind in the sauna, and settle into our cabin made for rest and connection.

Top guest favorite
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, 426 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 favorite
Cabin in Cape Girardeau
4.91 out of 5 average rating, 302 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.

Top guest favorite
The exterior of the cabin features a spacious porch with wooden railings and steps leading up to the entrance. Potted plants are positioned on the porch, and a warm wooden facade complements the surrounding natural setting.
Cabin in Anna
4.89 out of 5 average rating, 182 reviews

Contemporary Glamping with Native American Appeal!

Luxury Glamping with a taste of Native America! Stay in a hand-hewn oak timber cabin, on the historical "Trail of Tears" in Union County, Illinois. This lodging offers the rustic appeal of an authentic cabin in the woods, with the all the creature comforts and all year around outdoor hot tub. *If you do not find your desired date available, be sure and check our twin cabin listing at AdamsRock Cabins, Cabin #1.

Top guest favorite
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, 443 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

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