Holiday rentals in Charleston

2BR A-Frame Cabin w/ Hot Tub Near Wine Trail

Note: The large pond behind the cabin is being rebuilt at this time. See photo #6. White Oak Cabin is the middle A-frame on a scenic property with three cabins, each with its own outdoor space. This cozy retreat features two queen beds, a hot tub, furnished kitchen (cooktop + convection microwave), Smart TV, WiFi, and a workspace. Just minutes from ziplining, Giant City State Park, the Shawnee Wine Trail, and nearby public land, it’s a great base for couples, friends, and small families explor

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.

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.

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

Cobden Retreat in the Woods

Eva’s Roost Retreat Cabin 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.

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.

Magnolia Manor. Vintage cottage w/ Queen suite.

Welcome to our charming cottage nestled on 5 acres and surrounded by farmland —your perfect, peaceful retreat! Your cottage is to the left of the main home. Please see pictures for details. You may also get to meet Lucky, our friendly dog, who’s sure to make your stay more special. While you are welcome to pet him please do not allow him in the cottage. We are a pet free Airbnb and it’s important to maintain our integrity for those w/ pet allergies. Thank you!

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.

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.