Holiday rentals in Jackson

Farm Stay-Second Wind Cottage - Graham Estates LLC

Come get your second wind at our peaceful cottage designed for relaxation. Your family will love this quiet, serene home located up a scenic driveway. There is a large yard where you can feed the goats, enjoy the hot tub, or even end the day with a campfire. There is a walking trail around the property or you can drive approx. 35 minutes to Red River Gorge for an array of activities including kayaking, rock climbing, and hiking. So many memories are awaiting to be made at Second Wind Cottage.

Mountain Dream Cabin -Fish Pond+Fenced Yard+Stalls

Escape to a peaceful cabin with a wraparound porch perfect for soaking in the beauty of nature. This pet-friendly retreat features a fenced yard and space for trailer parking, plus four horse stalls available upon request. Enjoy catch-and-release fishing in the stocked pond, or explore nearby attractions: 25 minutes to Berea’s historic downtown and Pinnacle Trails, and 30 minutes to Flat Lick Falls and Sheltowee Trace. Unwind, explore, and experience the charm of our small-town getaway!

Lakes Creek Log Cabin

The two door "saddlebag" cabin is surrounded by the Daniel Boone National Forest and near McKee, a Kentucky Trailtown. Nestled in a small valley, our quaint cabin is the perfect mountain getaway. Built in 1894, by the Lakes family, it has a romantic, rustic and nostalgic feel. If you are a history buff, interested in Appalachian culture, or just want a charming, outdoorsy and secluded getaway, this cabin is for you. After making your reservation, be sure to check out the "House Manual".

Cliffside Romantic Retreat LOVE

Fall in love at the unique and serene "Tis So Sweet Cliffside Cabin". The space is designed for a lovers retreat with luxuries of a spa bathroom, massage chair, fire table, recliner seat hot tub, and much more! This newly built cabin is peacefully secluded, yet still only a few miles away from the Natural Bridge State Park, Red River Gorge, Daniel Boone National Forest, underground kayaking, zip lines, rock climbing, swimming, delicious food and many other local attractions.

The Homestead at Hundred Acre Holler

Hundred Acre Holler is a beautiful stretch of land in the Appalachian Mountains near Campton, KY. With exceptional hiking, fishing, and hunting opportunities, incredible views, and just 15 miles from Red River Gorge State Park and the Kentucky Reptile Zoo, Hundred Acre Holler is the perfect place for a weekend getaway, or a home away from home. This listing is for Homestead, suitable for up to four guests. For other cabins, please see our listings.

Red River Gorge Turtle Falls Hot Tub Firepit Wi-Fi

Welcome to cozy Turtle Falls, one of the newest, most beautiful cabins In Red River Gorge! The living space is open and inviting. The cabin is ideally situated 15 minutes from hiking, climbing, and attractions. Beautiful décor, a custom shower, and a gourmet kitchen are just the beginning. Enjoy the covered deck with hot tub, grill, Fire pit and a trickling waterfall that runs year-round. We'd love to welcome you to experience it for yourself!

Hill Haven | Cozy Cabin Escape + Hot Tub

Welcome to Hill Haven, your peaceful escape tucked away in the heart of Red River Gorge. This thoughtfully designed tiny cabin blends modern comforts with breathtaking natural surroundings to create a cozy retreat made for adventurers, nature lovers, and stargazers alike. Proudly owner-managed, Hill Haven offers a personalized stay you won’t find with big property companies, just warm hospitality and true attention to detail!

"Cozy Dumplin" - Warm & Modern Stay in RRG/Auxier

A perfectly located tiny cabin in the heart of Red River Gorge! Cozy Dumplin will indeed give you that "cozy cabin" feeling but with a more modern flare. This newly renovated property backs directly up to Daniel Boone State Park and is centrally located within minutes from Skybridge Road, Tunnel Road, and Natural Bridge State Park. Your family will be conveniently nestled next to the RRG's top hikes, eats, and adventures!

Lover's Leap, Cabin # 2

This cabin is set back into the woods for a little added privacy Queen bed,sleeps 2 persons. Perfect place for a romantic getaway. This is a very quiet place even with other cabins rented, you feel as though you're in your own little world. Come visit, you be sure to come back! ALL pets must be in a crate when left unattended in the cabin! We now offer limited TV although reception is poor.