Vacation rentals in Olive Hill

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Top-rated vacation rentals in Olive Hill

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

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Guest favorite

Cabin in Campton

4.91 out of 5 average rating, 35 reviews

LakeFront -Private Dock-Kayak & Canoe -Petfriendly

Our 4-br, 3.5-ba lakefront cabin sleeps 12 and offers serene, picturesque views with a private dock with Kayak &canoe. Unwind in the luxurious hot tub on the deck. Inside, enjoy the comfort of 3 queen beds, 2 full beds, a twin, and a full pullout couch. Stream your favorite shows with Roku & YouTube TV & end your days by the outdoor fire pit under the starry sky. Pet-friendly & perfect for families/groups, this charming cabin promises an unforgettable getaway filled with relaxation & adventure.

Guest favorite

Tiny home in Frenchburg

4.93 out of 5 average rating, 15 reviews

Brand New! The Mighty Acorn, Bungalow at the Gorge

Come retreat to this charming cabin nestled in the woods. Surrounded by cliff walls and lush greenery, this private oasis offers a peaceful and serene escape from everyday stress. Step inside to find 2 queen bedrooms, a kid's loft with 2 twin beds, and stocked kitchen. Whether you're snuggled up by the firepit, soaking in the hot tub or enjoying breakfast on the deck, every corner of this home exudes warmth and comfort. This is a true sanctuary where you can unwind, recharge, and reconnect.

Guest favorite

A cabin is nestled among tall trees, surrounded by lush greenery. A gravel pathway leads to the entrance, where a covered porch is visible. Two outdoor chairs are positioned nearby, offering a spot to enjoy the serene landscape.

Cabin in Frenchburg

4.96 out of 5 average rating, 137 reviews

Shine On near Red River Gorge!

A cozy little getaway located at the entrance of Indian Creek Resort!! Keep it simple at this peaceful and centrally-located place. Amazing cabin located near Red River Gorge, Daniel Boone National Forest and Cave Run Lake. A Private Backwoods wonderland!! A short scenic drive(20-40 minutes) to everything the area has to offer. Centrally located between Kentucky's most desirable hiking trails. Forget your worries on the spacious back deck, relax and unwind in the hot tub. 1bed/1bath

Superhost

A fire pit surrounded by two gray chairs sits on a gravel path, providing a cozy setting for gathering. The cabin, with windows glowing warmly, is positioned on a grassy slope, framed by trees under an evening sky.

Cabin in Pine Ridge

4.8 out of 5 average rating, 105 reviews

Smallwood Cabin-RRG-LUX-hot tub | wifi

Welcome to Smallwood Cabin! Exquisite attention to detail and quality abounds! Newly built in the heart of all the Gorge has to offer. Luxury linens, rugs, and decor set this place apart from others. Fully custom bathrooms with unique fixtures, walk in shower, and onsite laundry make your stay comfortable. Reminisce around the outdoor fire pit overlooking a tranquil pond or in the private hot tub! Easy check in, last min booking, & close to nature make the whole experience refreshing!

Top guest favorite

A modern black exterior house is surrounded by vibrant fall foliage. Large windows allow natural light into the space, while a small deck with a railing provides additional outdoor access. Lush greenery and ornamental plants enhance the inviting appearance of the property.

Cabin in West Union

5 out of 5 average rating, 50 reviews

Crow's nest couples retreat !

This property was built, specifically with couples in mind to relax,and reconnect. New 6person hot tub with led lights ,everything you would need is provided . Just bring food and cloths. its extremely quiet off the gravel road located in the heart of amish country. provided all kitchen supplies, bathroom supplies,plenty of fire wood, and grill .no wifi location to remote. smart tv. use your hotspot. good cell service. you can book with confience with us , your 100% satisfaction. a must

Superhost

The Manor House is situated on a cliffside, surrounded by lush greenery and towering trees. The residence features a wrap-around deck, enhancing its panoramic views of the natural landscape. The circular driveway leads to the entrance, which is framed by expansive woodland.

Cabin in Leeco

4.84 out of 5 average rating, 50 reviews

Jaw Dropping Getaway in the Heart of RRG!

Discover the one-of-a-kind Manor House, nestled in the heart of Red River Gorge's Cliffview Resort, and positioned directly beneath the awe-inspiring Milky Way. Aptly known as the "Island in the Sky," this iconic residence at Cliffview rests at the tip of a picturesque point, surrounded by towering rock cliffs and pristine woodlands below, with the stars twinkling above. With 5 bedrooms, 3 bathrooms, and accommodations for 16 guests, this cabin is ideal for gatherings on any occasion!

Guest favorite

An aerial view highlights the modern log cabin nestled among tall trees, with a glimpse of a serene lake reflecting the surrounding greenery. A wooden bridge extends across the water, enhancing the cabin's natural setting.

Cabin in Rogers

4.89 out of 5 average rating, 38 reviews

Klyfta Haus 4Br Lakeview HotTub FirePit EV Charger

Welcome to Klyfta Haus! Perched on a serene 1-acre hillside with breathtaking lake views. This modern 4-bedroom 3-bath log cabin offers a hot tub, fire pit, EV charger, games, shuffleboard, and ample parking. Unwind while taking in the sleek, rustic interior, or savoring the views from the deck, it’s the ultimate blend of adventure and relaxation. Conveniently located near all the Red River Gorge attractions, it’s perfect for a romantic escape, family getaway, or group adventure.

Superhost

A close-up of a pine cone is nestled among green pine needles, showcasing textured brown scales. The background features blurred foliage, providing a natural setting that enhances the earthy tones of the cone.

Camper/RV in Stanton

5 out of 5 average rating, 4 reviews

Peace Hideaway

Reconnect with nature at this peaceful escape. It’s the simple things that bring peace and relaxation to your life. It’s beautiful, small, simple and just the right size for two. There’s an outdoor shower to wash away dirt and mud from hiking and rock climbing all day at the gorge, a nice size bathroom inside if you prefer to take a hot relaxing shower before you grill or use the outside kitchen for a delicious dinner. Sit around the fire pit and enjoy the rest of the night.

Top guest favorite

A view of the kitchen featuring a dark countertop with bar stools. An open archway leads to the living room, which contains a sectional sofa. A trash can is positioned against the wall, and the textured flooring contributes to the overall warm ambiance.

Home in Ashland

4.97 out of 5 average rating, 122 reviews

Roosevelt Retreat - 2BR, 2 Bath Craftsman

Charming, updated Craftsman in South Ashland which is 1 of 2 on the property (home located at the front of the property). You will find a 2 bedroom (1 king, 1 full bed/1 xl twin bed), 2 bath (one bathroom contains the washer and dryer), fully furnished kitchen, living room with sectional, and 3 flat-screen smart TV's. This is a quiet, residential neighborhood within a 10-minute walk of Putnam Stadium and a 5 -minute drive to downtown. NO SMOKING - NO ANIMALS

Top guest favorite

Cabin in Stanton

4.98 out of 5 average rating, 104 reviews

Briar Patch Cabin-RRG | Fire Pit | Sunset | Wi-Fi

Located along the outskirts of the Red River Gorge Scenic Byway, The Briar Patch is perfectly situated to host travelers who are seeking both privacy and convenience. This cabin was thoughtfully designed to host anywhere from 1 to 6 people without making guests feel too cramped or in a space that’s too large to feel comfortable. Its rustic interior creates the perfect mood for this dreamy mountaintop vacation home.

Guest favorite

A vast landscape is presented, showcasing rolling hills and valleys adorned with vibrant trees in various autumn hues. A rocky outcrop in the foreground features a small pool of water, reflecting the surrounding greenery and cloudy sky.

Home in Stanton

4.89 out of 5 average rating, 171 reviews

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.

Superhost

A modern cabin features a dark exterior with large glass doors, allowing glimpses of the cozy interior. A small seating area outside includes four blue Adirondack chairs arranged around a stone patio, surrounded by greenery and trees.

Cabin in Stanton

4.87 out of 5 average rating, 237 reviews

THE WILDS | 100 Acres | Sunset & Sunrise Overlook

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.