Family-friendly vacation rentals in Estill County

4.91 out of 5 average rating, 160 reviews

A spacious studio interior features warm wooden paneling and a cozy layout. A dining table with four chairs is positioned near the fully equipped kitchen. A queen-size bed is set against the far wall, complemented by a patterned rug and soft lighting from the ceiling fan.

Apartment in Pine Ridge

CLIMB ON INN - Apt 2 - Naturally Gorgeous- RRG

Discover the serenity of nature in this charming studio nestled near the incredible trails and scenic wonders of Red River Gorge. Ideal for adventurers or tranquility seekers, it features a cozy queen-size bed, daybed with trundle, and a fully stocked kitchen. Embrace comfort in a space designed for relaxation and inspiration. Perfectly positioned for outdoor enthusiasts, this haven offers a plush launchpad to Kentucky's most beloved landscapes. Get ready to hike, climb, and unwind in style!

4.93 out of 5 average rating, 736 reviews

The cottage exterior features a welcoming front porch with wooden rocking chairs and a swing. Colorful artwork adorns the walls, complemented by a garden of flowers. The door is a vibrant blue, and tall trees provide shade overhead, creating a peaceful entrance.

Home in Berea

Berea Painter's Cottage

Eclectic, clean, comfortable cottage featuring original artwork, located in walking distance of Berea College Campus, Artisan Village/Old Town area, Art Galleries, Unique Shops, The Lot, Rebel Rebel, Nightjar, Sunhouse Craft, and Native Bagel. A short drive to the Pinnacles and Kayaking at Owsley Fork Lake. The location is great. A cozy patio in front of the home with a swing and a tree canopied deck in back that feels like being in a treehouse. Basic TV channels and high-speed internet.

4.94 out of 5 average rating, 332 reviews

A covered outdoor space is featured with wood paneling and ambient lighting. The area includes a hot tub in the center, surrounded by seating and a TV mounted on the wall. Large windows offer views of the wooded surroundings, enhancing the peaceful vibe.

Cabin in Campton

Frog Song Cabin w/Hotub@RedRiverGorge

In the heart of Red River Gorge, surrounded by the woods for your privacy in Cliffview resort, this renovated cabin (October 2024) is ready for your next getaway. Frog Song has always been a guest favorite as it is close to all things hiking and climbing yet private and secluded. Enjoy the brand new, large covered Hot Tub area with outdoor seating, TV and fire pit. You won't want to leave! Discover this charming 2 bed, 1.5 bath cabin close to all things in RRG. Hike, Climb, Relax, Repeat

4.94 out of 5 average rating, 71 reviews

A charming farmhouse exterior features a black metal roof and white walls. Hanging ferns adorn the front porch, which is surrounded by well-maintained flower beds and greenery. A small outdoor seating area with red chairs complements the inviting façade.

Home in Campton

Emilys Welcome Inn B&B Minutes from Red Rvr Gorge.

Escape to a bygone era at our charming 1880's Vernacular Victorian-style farmhouse. Immerse yourself in history, surrounded by Lacy family heirlooms. Enjoy the perfect blend of nostalgia & modern convenience. We have good wifi & cell service. We welcome children but they will need supervision. Nov 1 - Jan 10 children are discouraged due to the Christmas decor. Sorry, we cannot accommodate pets. Experience the warmth & hospitality of our historic farmhouse B&B. Book your stay today

4.9 out of 5 average rating, 239 reviews

A rustic cabin made of logs is set against a backdrop of rolling hills and dense trees. A vibrant red roof contrasts with the natural surroundings. Morning mist hovers over the landscape, creating a serene atmosphere in the valley.

Cabin in McKee

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".

4.91 out of 5 average rating, 238 reviews

Two patterned armchairs are positioned facing each other beside a window, allowing natural light to illuminate the space. A small table is placed between the chairs, holding a decorative item and a lamp. Sheer curtains frame the window, adding to the inviting ambiance.

Home in Berea

High on Berea

High On Berea is a lovely home that was built in 1938. The home sleeps 4 people. The space includes a kitchen, dining room, bathroom, living room and 2 bedrooms. The master bedroom has a queen bed and the second bedroom has a double bed. Living quarters are on one level with 4 stairs leading into the house and 2 stairs at the curb of house. Parking is available in driveway to the left of the home and in the back yard. City ordnance does not allow parking in front of the house.

4.9 out of 5 average rating, 625 reviews

A charming treehouse is situated among dense greenery, featuring a wooden deck with seating and a staircase leading down to a pathway. The entrance is highlighted by a wooden sign labeled 'Lion's Lair,' blending seamlessly with the natural surroundings.

Treehouse in Stanton

The Lions Lair - Remote Treehouse

Welcome to The Lion’s Lair—Kentucky’s most wish-listed treehouse, perfect for romantic escapes, family adventures, or getaways with friends. Nestled on private land, enjoy coffee on the balcony, stargazing from the top deck, or swinging below. End your day with s’mores by the fire pit. With trails like Gray’s Arch and Natural Bridge nearby, adventure is always steps away. Just 15 mins from local favorites like Miguel’s Pizza, coffee shops, mini golf, and much more!

5 out of 5 average rating, 28 reviews

A view of the campsite features well-maintained gravel paths leading to several camper trailers. Lush greenery surrounds the area, with trees providing shade. The scene is complemented by a gentle slope in the background, enhancing the natural setting.

Campsite in Berea

Water & Electric Campsite #1

Creekside camping with electric and water (NO SEWER OR DUMP STATION - YOU MUST HAVE HOLDING TANKS). Spaces are small and located in a social area of the farm (NOT secluded) so sites are best suited for campers that are 25' or less or 2 four-person tents. 30 amp / 50 amp / 110 volt plugs. Nearby outhouse and seasonal bath house available. Message us with any questions. NO PETS or ESAs - NO EXCEPTIONS!

4.87 out of 5 average rating, 111 reviews

The cabin presents a rustic exterior, featuring a stone chimney and wooden porch decorated with hanging plants. Surrounded by lush green trees, the structure blends with the natural forest environment, providing a serene escape. Sunlight filters through the leaves, creating dappled shadows on the ground.

Cabin in Slade

Big Rock Log Cabin

Big Rock Log Cabin is a wonderful vacation getaway in the forest of Red River Gorge, Kentucky. 5 minutes to Natural Bridge State Park and Red River Gorge. Sleeps 8, full kitchen, Great Room with fireplace. Tucked under a 40 foot cliff with campfire pit in a large rock shelter. NO SPRING BREAKERS or parties. Big Rock is professionally cleaned after each reservation following CDC guidelines.

4.92 out of 5 average rating, 250 reviews

A modern cabin is nestled among lush greenery, featuring a sleek black exterior and a gabled roof. A stone pathway leads to the entrance, with tall trees creating a natural canopy overhead. A sign with 'LEWIS' prominently displays at the front.

Cabin in Stanton

Luxury | Private Overlook & Hiking | Creek & Pond

100+ acre private preserve & surrounded by 65K acres of National Forest connected to RRG. Private hiking trail to Sunset Point overlook. Creek meandering entire property with fossil rocks and swimming holes. 1/2 Acre Pond with fishing (Catfish & Bass) & onsite Kayaks & Paddleboard. Just 15 minutes from Red River Gorge: world renowned rock climbing, waterfalls, hiking, and more.

4.94 out of 5 average rating, 104 reviews

A welcoming house is set against a vibrant sunset sky, with a well-maintained grassy lawn in front. The porch area features seating and potted plants, inviting relaxation in the natural surroundings. Green trees and shrubbery frame the property, adding to the serene atmosphere.

Home in Beattyville

The Old Orchard Inn.

Are you here to climb, hike, or just relax? We've got you covered for all, we're located on the Daniel Boone Backcountry Byway, 5 mins from Miller Fork. 5 mins. from PMRP. This is the perfect climber house but also the perfect place for a quiet week/end in the woods. Close to Natural Bridge State Park and Daniel Boone NF. Come unwind and relax with us.