
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.

1-bedroom tiny home located in historic Bloomfield
Kick back and relax in this calm and stylish space located minutes from the Missouri Veterans Cemetery and The Stars and Stripes Muesum and Library. 1bdrm/1bath comfortably sleeps 2 and is furnished with everything you need. Inside you will find all new appliances, bedding, and linens. Circle drive with parking. No smoking or pets allowed. Local restaurants include Las Brasis and Elderland. Or try out locally owned businesses just 6.5 miles drive to Dexter such as Hickory Log and Dexter BBQ!

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.

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!

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.

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

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.

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!

Perfect Couples Retreat - firepit
Come stay at The Perch, a rare and memorable little hideaway perched on a hillside with the best sunset views in Western Kentucky. Cozy king loft, full bath, tiny kitchen, and a porch perfect for morning coffee or evening cocktails. Hang out at the fire pit and grill area while you take in the stars and fresh air. Our four fur off-leash babies love meeting new friends—so you gotta love pups too! Perfect for couples or solo travelers.

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.

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.

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.

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
Other great holiday rentals in Charleston

Modern Luxury Cabin, Fireplaces, Hot Tub Paducah

The Center Country House

Newly Renovated 3 Bedroom 2 Bath Home - Sleeps 9

Hosta House

Secluded Shawnee Forest Cabin Creek View | Hot tub

The Cottage, Rusted Route Farms

A-Frame @ Inspiration Village on Boulder Creek

RiverSide Barn Suite on the Mississippi River.
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