
Holiday houses in Charleston
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Top-rated holiday rentals in Charleston
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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.

The Cottage, Rusted Route Farms
You won’t forget your time in this romantic, memorable place. The Cottage at Rusted Route Farms is a 1 bedroom beautiful suite on an old 10 acre farm history galore. A picturesque pond is settled next to The Market our onsite Restaurant that will be serving food and drinks to be ready on your arrival or for a certain time that you choose. The over 125 year old barn has been renovated to keep the history alive and is located here on site. This retreat is located right outside Cape Girardeau.

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.

Shawnee Hiking!Hot tub!Fire Pit!Wine Trail!
WELCOME TO LUXURY GLAMPING ON THE SHAWNEE WINE TRAIL OF BEAUTIFUL SOUTHERN ILLINOIS. You will be resting in an authentic oak timber cabin, built on the historical "Trail of Tears" in Union County - Anna, Illinois. This lodging offers the rustic appeal, a taste of Native America with the comforts of contemporary amenities including an outdoor hot tub all year long! *If you do not find your desired date available, be sure and check our twin cabin listing at AdamsRock Cabins, Cabin #2.

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

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

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.

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.

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!

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.

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
Other great holiday rentals in Charleston

The Center Country House

Newly Renovated 3 Bedroom 2 Bath Home - Sleeps 9

Hosta House

Farmer Ty’s ranch house from ‘Farmer Wants a Wife’

Edgewood Retreat

A-Frame @ Inspiration Village on Boulder Creek

Family Home near the MS River with a toy Room

The Gathering Place
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