
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.

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

Ma's Cabin, Alto Pass, IL. Fine country lodging.
Cute and country remodel done in 2019. Recent new appliances, furnishings, flooring, heat & A/C, washer & dryer. Cabin is secluded and quiet plus 1/2 mile from Alto Pass Lookout Point and right in the middle of many award-winning wineries. 15 miles from Carbondale 4 miles from Giant City 30 miles from Garden of the Gods 6 lakes within 10-mile radius Hundreds of miles of hiking trails in nearby Shawnee National Forest 6 miles from Bald Knob Cross Please, no dogs! No smoking in cabin!

Tiny Cabin* Near Blue Sky*Shawnee*Pet Friendly
Après Vine Tiny Cabin is your escape to a serene minimalist cabin in Shawnee National Forest! Just 5 min to Blue Sky Vineyard, hiking, zip lines, and I-57, this retreat blends adventure and tranquility. Relax by the fire pit, take in sunsets, rolling pastures, and woodlands. No Wi-Fi or TV ensures a true digital detox. Friendly livestock guardian dogs may greet you. **Pet-Friendly when added to reservation! Perfect for nature lovers seeking a peaceful getaway or the minimalist adventurer!

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

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.

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!

Glamping Dome · Hot Tub, Fire Pit & Forest Views
One of Illinois' most-favorited Airbnb listings — and once you arrive, you'll understand why. Soak in your private hot tub under a canopy of stars, wake up to panoramic forest views through floor-to-ceiling dome windows, then explore 8 acres of total seclusion. King bed, full kitchen, washer/dryer, fire pit, and charcoal grill all included. Intentionally TV-free — the night sky is the entertainment. Minutes from Shawnee National Forest trails and wine country.
Popular amenities for Charleston holiday rentals
Other great holiday rentals in Charleston

Dad's Place

2-Story Glass Dome Treehouse W/ Hot Tub & Arcade

Vibrant Tiny Home Retreat | Creek & Fire Pit

Gram's Cabin at Bald Knob

Shawnee National Forrest Luxury Escape, Pets Ok

Covered Bridge Cabin | 75-Acres near LoE/I-57/I-24

Family Home near the MS River with a toy Room

Coalminers Cabin at Ramp 11 Retreat by Concord Sun
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