Holiday houses in Estill County

Nan's Cottage on Songbird Hill

Does a treehouse vacation sound inviting but cramped? Then you'll love our quaint cottage with a spacious deck overlooking the forest! This older home has been reclaimed from the wild and is decorated with antique and vintage finds, lending a "cottage-core" or "grandma-core" feel. We think you will find it enchanting as you are serenaded daily by a variety of wild birds. Although you'll be hidden away in the trees, you may hear traffic and farm activity. 4WD or AWD required year round!

The Towner ~ Near Red River Gorge, Ky

Conveniently located to some of the best spots Eastern Ky has to offer, and yet, The Towner still has the small town country charm that has come to be expected of the Red River Gorge area. Guaranteed clean and comfortable!! Perfect for extended stays or short “getaways”. Located within city limits, The Towner is perfect for those who like adventure with the convenience of the city. High Speed WiFi, within walking distance of groceries and Restaurants, yet only 8 miles to Slade Welcome Center.

Sally’s Point of View-secluded & peaceful cabin

Thank you for choosing Sally’s Point of View! We hope you’ll enjoy the peace of this place as much as we do.Our quaint and cozy cabin is nestled in the midst of ten acres with hiking on property.A welcoming front porch, back deck that looks into the forest and up to our cliffs,balcony off the master bedroom.There is a large fire pit a short walk from the cabin.Minutes from beautiful Red River Gorge hiking,climbing,natural bridge,Miguel’s,zip-lining, & canoeing. Arcade & games on rain days

Rocky Flatts Cabin Pets Welcome No cleaning fee

Adorable two bedroom with new mattress on sleeper sofa and cot capable of sleeping 6, one bath, located on working farm. Lots of wildlife. Beautiful country scenery. Located ten minutes from Natural Bridge State Park and the Red river gorge and Hollerwood ATV Park. Lot of room to park vehicles and atv's. Just sit on porch or in hot tub and relax. No 4x4 vehicle needed for access to cabin. Please clean up after your pets in the yard. We have supplies for pet clean up on porch.

Hemlock Hideaway: Red River Gorge, Pool, game room

Hemlock Hideaway at Red River Gorge is a 3 bedroom, 2 bath cabin that can sleep up to 10. The cabin features a pool, hot tub, game room, and electric vehicle charger on a private 2.5 acre setting. The home has two king sized beds, three full sized beds, a twin trundle bed, twin sleeper chair and queen sleeper sofa. There is a fully stocked kitchen and free onsite laundry. All of this and so much more and only a 20 minute drive to the Red River Gorge, Natural Bridge State Park area.

Cabin -40 acres, Hot Tub, 3-Sided Porch, Rec Room

Near the Natural Bridge, Hollerwood ATVs, & RRG! Get away from the hustle & bustle of life & reconnect w/ nature! Deep in the forest, u will discover a beautiful cabin overlooking a bluff in the magical Appalachian Mtns. Add a rec room, 3-sided porch w/ a pair of 6’ porch swings, 2 electric grills, hot tub, fire pit, small target range (+ much more) & you may never want to leave! 4 bedrooms, but can sleep 16+. Must b 24 yrs or older to rent. Msg with questions!

Stay at The World Famous Holla Holler in Downtown

The Songwriter Suite at Holla Holler music venue. This historic 1930's building space is a music venue/ listening room when not rented out to travelers on Airbnb. The Studio Suite has 3 beds and sleeps up to 5 people comfortably. There is a stage with a 40 seat capacity. It has state-of-the- art Bose audio, lights and guitars. *Events are fine with pre- approval. We are nestled right in Downtown Irvine, walkable to shops and dining. Pets ok

Maple Point - Dream Cabin in RRG

Welcome to Maple Point, an immaculate 1 bedroom + 1 bath cabin located in the heart of Red River Gorge. Completed in 2024, this property was thoughtfully created by a builder and designer to provide guests with a comfortable and memorable space to enjoy this region of Kentucky. Whether you are looking for a central base from which to explore, a quiet getaway where you can relax, or an inspiring space to work, we would love to have you come stay.

RRG Climbers Choice Stay-Wifi- No cleaning fee

We'll have you feeling like a local in two days minimum and in a town so friendly you might just become one. Fully furnished duplex (SIDE B) is minutes drive from the best Red River Gorge hiking trails, climbing, Miguel's, Natural Bridge State Park, The Gorge Underground, Callie's Lake, La Cabana & Kroger. On the Scenic Byway in Stanton. Side A & B can be booked together if availability allows.