House holiday rentals in Olive Hill

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Top-rated house rentals in Olive Hill

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Top Guest favourite
Home in Russell
4.98 out of 5 average rating, 375 reviews

Home w/a River & Bridge view, a HotTub & an Igloo

RIVERTIME - A house w/a hot-tub & an igloo. Experience it all on the bank of the Ohio. The views are magical & soothing to the soul. Make your way into the backyard & you will quickly forget that you are in an Eastern KY residential area. It’s often stated by our guests that the view rivals some of the top landscapes & city skyline from around the world. You can walk to downtown Russell & enjoy shopping, great food & tasty drinks. Only a few mins from Ashland KY & 20 mins to Huntington, WV

Superhost
A well-lit living room features a large, plush sofa and a leather coffee table placed on a textured area rug. A television is mounted above a modern fireplace, while a staircase and a separate dining area can be seen in the background.
Home in Ashland
4.83 out of 5 average rating, 206 reviews

The Roundabout Retreat

Circle back to the "The Roundabout Retreat," a delightful 3BR home a heartbeat away from UK King's Daughter Medical Center. Perfect for families, this gem features a chef-ready kitchen, private fenced yard, plush king bed in a large master, new 58" TVs, office space, and a quaint dining room. Enjoy the convenience of our LG Washtower, a selection of board games for fun evenings, and decor that’s both elegant and welcoming. Your tranquil downtown haven melds style and convenience beautifully.

Guest favourite
A comfortable living area features a light brown sectional sofa adorned with black and white checkered pillows. A wooden coffee table is positioned in front, with a decorative bowl placed atop. Natural light filters in through a window, accompanied by a cozy lamp beside the sofa.
Home in Stanton
4.93 out of 5 average rating, 195 reviews

The Towner

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.

Guest favourite
A rustic cabin features a striking black exterior with a freshly painted red roof. A wooden deck with seating is visible, surrounded by lush greenery. An air conditioning unit stands discreetly on the side, providing comfort during warmer months.
Home in Campton
4.82 out of 5 average rating, 132 reviews

Cozy Cabin for 2 in the Heart of RRG!

Experience the perfect getaway at our rustic couples cabin, nestled within the breathtaking beauty of Cliffview Resort. With an array of outdoor adventures right at your doorstep, this cabin promises an unforgettable vacation. Discover a world of excitement with ziplines, Via Ferrata, serene lakes, hiking trails, fishing spots, and a refreshing swimming spot. But that's not all, prepare to fall in love with the awe-inspiring views that surround you at the nearby Natural Bridge State park.

Top Guest favourite
A modern black house is set on a rocky landscape, surrounded by lush greenery. A wooden post carved with bear figures adds natural charm. Large windows invite light into the home, enhancing the connection between indoor and outdoor spaces.
Home in Wellington
4.99 out of 5 average rating, 143 reviews

Luxury Cliffside Hammock House

Escape to a modern luxury hammock oasis: with cozy indoor & outdoor loft-net hammocks, memory foam beds with MyPillow pillows for supreme comfort, and MyPillow towels enhancing the spa-like bathrooms featuring rainfall showers and body jets. Adventure awaits with a private trail into Daniel Boone National Forest, a hot tub, and a pool table. This space isn't just a stay but an experience, designed for those seeking luxury, comfort, and a touch of adventure. Not Suitable for children.

Top Guest favourite
The cottage's exterior is characterized by a welcoming porch featuring rocking chairs and a bench. Black star accents adorn the light-colored siding, framed by green grass and trees. Large windows invite natural light, enhancing the view of the surrounding fields.
Home in Morehead
5 out of 5 average rating, 113 reviews

Sunset Cottage

Sunset Cottage is located among the farms and fields of Morehead, KY. Conveniently situated off of I-64, within 10 min. of Cave Run Lake, App Harvest, Ind. Stave Co., and MSU. This newly remodeled 2-bedroom home has 1 queen, 1 full, & 1 twin bed. A quaint living room with an elec. fireplace, full kitchen, dining area, washer/dryer & an outdoor space that includes a gas grill and fire pit. There is plenty of room to park your boat and a porch to relax and enjoy the beautiful sunset

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
4.94 out of 5 average rating, 203 reviews

The Retreat, 30 min from RRG/Natural Bridge

Modern 3 Bedroom 2 Bath on 11.5 acres roughly 20 miles from Red River Gorge. Entire house has been renovated. Starlink Internet, Electric fireplace, Smart TVs in all bedrooms/living room, Pinball Machine, and Ceiling fans in all bedrooms/living room. Fire-pit area with porch swing, chairs, bench for food, picnic table, and string lights for entertaining. The house sits on 11.5 acres, guests are welcome to walk the property. Large wrap around driveway for easy arrival/departure

Guest favourite
A spacious interior is highlighted by warm wooden walls and ceilings, creating a cozy cabin feel. A comfortable leather sofa and two chairs are arranged around a coffee table, while barn doors lead to the sleeping areas in the background. Soft lighting provides a welcoming ambiance.
Home in Pine Ridge
4.93 out of 5 average rating, 142 reviews

Comfy Woodsy Stay| Near Hiking in RRG| Firepit

Lumber Lodge is in the heart of Red River Gorge! This 3-bed cabin backs directly up to Daniel Boone State Park and has so much to offer. This is the place where memories are to be made and s'mores to be devoured (especially around the fire-pit area). Staying in this neck of the woods will have you 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.

Top Guest favourite
A living room space features a brown sectional couch positioned around an extendable coffee table. Sunlight filters through windows adorned with white blinds, and a ceiling fan provides ventilation. Wall decor includes welcome signs and decorative metal wall art.
Home in Ashland
4.97 out of 5 average rating, 161 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 favourite
A retro-inspired kitchen space features a round white dining table surrounded by four red chairs. Black and white checkered flooring complements the vintage decor, while a light-filled window dressed with playful curtains adds warmth. A classic phone and wall clock are visible on the gray walls.
Home in Stanton
4.94 out of 5 average rating, 111 reviews

Climbers Choice RRG 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 A) 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. Located in Stanton at beginning of Scenic Byway. Side A & B can be booked together if availability allows.

Guest favourite
A charming house is visible from a distance, featuring a welcoming porch supported by wooden railings. Lush greenery and bright yellow flowers create a vibrant landscape, enhancing the exterior. The house is complemented by a backdrop of trees, adding to the inviting atmosphere.
Home in Flemingsburg
4.98 out of 5 average rating, 343 reviews

BLUE MOON LODGE- --UNWIND, CONNECT, REFUEL, RELAX!

If you are looking for a absolutely breathtaking, cozy place for just a few days break, or a complete unique, custom vacation for your family, you have found the place. Come and see for yourself what all the 5 star reviews are about. Every now and then you run across a place that just lifts a weight off your shoulders as soon as you open the door, THE BLUE MOON IS THAT PLACE!!!

Top Guest favourite
The entrance to The Mail House features a covered porch adorned with hanging ferns and lights. A cozy seating area consists of a wicker sofa and chair, complemented by a welcome sign and a green door. Solar panels are visible above, facilitating sustainable energy.
Home in Pine Ridge
4.97 out of 5 average rating, 291 reviews

Mail House RRG (Historic Post Office)

The Mail House is a charming tiny home that once served as The Pine Ridge Post Office From 1950-2005. Located in the heart of the Red River Gorge and minutes to the areas most popular attractions. Guests will appreciate waking up in close proximity to trail heads in the Red River Gorge and Natural Bridge State Park, as well as world class climbing destinations.

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