Vacation rentals in Estill County

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Top-rated vacation rentals in Estill County

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favourite

A wooden cabin is perched on a bluff, surrounded by vibrant autumn foliage. The structure features a welcoming porch with multiple windows, showcasing the natural beauty of the Appalachian Mountains during fall.

Cabin in Stanton

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+. 10 miles to Natural Bridge. 24 yrs. or older to rent. Please msg us with questions!

4.92 out of 5 average rating, 122 reviews

Superhost

A spacious hot tub is surrounded by a wooden ceiling and screened walls, providing a sheltered area to relax. Sunlight filters through the trees outside, creating a serene environment. Comfortable seating options are visible nearby, enhancing the space for leisurely enjoyment.

Cabin in Stanton

Hot Tub, Fast WiFi, Netflix and Very Close to RRG!

Very secluded cabin in the mountains. Quiet and surrounded by woods. Huge backyard to walk your dogs! Nature walks, hiking and rock climbing are all just a short drive down the road to the famous Red River Gorge. Natural Bridge State Resort Park is only a 14 mile scenic drive. 7 person hot tub and all amenities included in your stay. A place to get away from the city, unwind and enjoy the company of those around you. Fresh mountain air, cozy moments to remember. Mountain Home is calling!

4.87 out of 5 average rating, 694 reviews

Superhost

The kitchen features modern appliances, including a stainless steel refrigerator, and warm wooden cabinetry. An island countertop with bar stools provides an inviting space for gathering. Natural light enters through large windows, highlighting the spacious layout of the area.

Home in Stanton

Hot tub, Fast WiFi, Fire Pit, Outdoor Theater!

Mountain Farmhouse. A place where you can relax, drink your coffee, listen to the sound of the birds in the morning the whippoorwills & crickets at night. On the back porch there is a hot tub to enjoy, an outdoor bar & dining area with a projector/home theater setup in front of the hot tub! A gas grill. WiFi & NFLX/Hulu/Disney. A beautiful old home recently remodeled with a wrap around driveway. 1 bedroom down. 2 bedrooms upstairs. Secluded location & plenty of space for entertaining.

4.78 out of 5 average rating, 214 reviews

Top guest favourite

Guesthouse in Stanton

Robbie’s Rest: Amazing Mountaintop Sunrises

2020 new unit with nice deck, wonderful mountain scape with amazing sunrises from your deck or the deck of the main house where host lives. 8 acres that sit where the rolling hills meet the mountains overlooking the Daniel Boone Forest. 35 miles from Lexington, you will enjoy the peace & quiet of the beautiful mountains. Minutes away from the trails, waterfalls & attractions of Natural Bridge State Park & the Red River Gorge! We hope you will visit us soon! *Sunrise is not always visible

4.98 out of 5 average rating, 376 reviews

Guest favourite

A newly constructed A-Frame cabin is set against a backdrop of bare trees and a clear blue sky. Steps lead up to a spacious deck, emphasizing the cabin's inviting entrance. The exterior features a combination of neutral tones and crisp lines, reflecting modern design.

Cabin in Stanton

New! Mountain Top A-Frame Cabin, The Triangles

Escape to your mountain top sanctuary where breathtaking views leave you in awe . This newly constructed A-Frame cabin invites you to immerse yourself in the tranquility of nature while indulging in modern comforts. Relax in the hot tub while enjoying stunning sunsets and gorgeous nature views all around. With meticulous attention to detail, each corner of this retreat exudes a personal touch, ensuring a truly unforgettable getaway amidst the wilderness. 20 mins to RRG! The Triangles

4.96 out of 5 average rating, 136 reviews

Guest favourite

Cabin in Clay City

Hemlock Hideaway Red River Gorge Recent Refreshed

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.

4.92 out of 5 average rating, 137 reviews

Top guest favourite

Home in Ravenna

The River House

Come stay and enjoy our lovely "River House". This house not only offers a comfortable home feeling stay, but also convenience to tons of entertainment and exploration. Located just outside of Ravenna in Estill County on the banks of the Kentucky River. It is a two-story, two bed, one bath house with existential views of the Kentucky River, river bottoms, and Appalachian Mountains. Porches with hammock chairs and patio furniture and windows upstairs to constantly take in the views!

5.0 out of 5 average rating, 21 reviews

Top guest favourite

A custom-built cabin is depicted, featuring a rustic wooden exterior and a covered front porch. Stairs lead up to the entrance, surrounded by green grass and mature trees. The sloped roof and large windows create an inviting presence in the serene outdoor setting.

Cabin in Irvine

Sadie’s Springs

Come home to the hills of Estill County, Kentucky in our custom-built cabin which offers a cozy interior & relaxing outdoor spaces. The sounds of nature and the serene views offer the opportunity to rest & reset. Your peaceful getaway is also centrally-located to nearby attractions. We are 10 minutes away from ‘town’ - the sister cities of Irvine & Ravenna & just 5 minutes from the nearest Dollar General. Come to Sadie’s Springs & make lasting memories in this home away from home.

4.97 out of 5 average rating, 78 reviews

Top guest favourite

Home in Irvine

Pauline's Paradise

Welcome to Pauline's Paradise! You can enjoy a quiet and relaxing stay in our 2 bedroom home, with an adjustable King bed in one and twin beds in the other. You'll find a full kitchen, washer/dryer, wifi and Roku TV. We welcome well behaved pets. Handicapped entrance ramp. We're 25 min. away from Natural Bridge, Sky Bridge, Red River Gorge, hiking, underground kayaking and more. We're less than an hour from Lexington. We ask that you refrain from smoking inside during your stay.

4.99 out of 5 average rating, 142 reviews

Top guest favourite

A charming cabin with a blue metal roof is surrounded by trees, showcasing a spacious front porch. Rocking chairs are arranged for relaxation, and the entrance is framed by a gravel path and neatly landscaped greenery.

Cabin in Stanton

Rocky Flatts Cabin Pets Welcome No cleaning fee

Adorable two bedroom with new mattress on sleeper sofa and cot capable of sleeping 4 one bath, located on a 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.

5.0 out of 5 average rating, 384 reviews

Top guest favourite

A modern living area features a spacious gray sectional sofa facing a sleek electric fireplace set against a black wall. A smart TV is mounted above the fireplace. Light wood flooring complements the room, with a small plant and decorative items on a coffee table.

Home in Stanton

*NEW HOT TUB*The Retreat. 30 min from RRG

Modern 3 Bd 2 Ba on 11.5 acres roughly 20 miles from Red River Gorge. Entire house has been renovated. Starlink Internet, Electric fireplace, Smart TVs in all rooms/living room, Pinball Machine, & Ceiling fans in all bedrooms/living room. Fire-pit area with porch swing, chairs, bench for food, picnic table, and string lights for entertaining. New HOT TUB added spring 2026. Guests are welcome to walk the paths on property. Large wrap around driveway for easy arrival/departure.

4.95 out of 5 average rating, 241 reviews

Top guest favourite

The cabin is set among trees, featuring a front porch with seating and hanging planters. A light gravel path leads to the entrance, showcasing a simple yet inviting facade with large windows and a sloped metal roof.

Cabin in Stanton

Gateway to the Red River Gorge

Get off the beaten path at this unique and tranquil getaway. Situated atop a small hill on a ridge traversed by a dead-end road, the 510 sq ft cabin is on a wooded lot. Ideal for couples, it is a one bedroom with walk-out deck, large front porch, and a tv room with futon. It has a well-appointed kitchen area with new appliances, cherry and tongue and groove pine paneling throughout, vaulted ceiling, solid oak flooring, large picture windows, and a tv/work area.

4.99 out of 5 average rating, 134 reviews