Vacation rentals in Olive Hill

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Top-rated vacation rentals in Olive Hill

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Guest favorite

The large A-frame house is nestled within a lush green landscape, surrounded by mature trees. The structure features a prominent front deck with ample windows, allowing natural light to fill the interior. A spacious lawn extends from the house, inviting relaxation in the serene country setting.

Home in Olive Hill

4.89 out of 5 average rating, 38 reviews

A Frame of Mind

Spacious country setting near Carter Caves, Grayson Lake, Rush Offroad, Cave Run Lake, and local Trail Town. This large A-frame is a relaxing family setting with enough space for trailer parking. Watch the wildlife from the multiple decks or even from the bed. This is a great home base for your Eastern KY adventures or a wonderful quiet getaway. It has electric fireplaces, a wood fire pit, a gas firepit, an electric smoker, a charcoal and gas grill, and two creeks to enjoy during your stay.

Top guest favorite

The exterior of a red brick home is depicted, featuring a sloping gray roof and a driveway leading to a garage. An American flag is displayed outside, complemented by a neat garden of colorful flowers and lush greenery flanking the entrance.

Guest suite in Ashland

5 out of 5 average rating, 131 reviews

Cozy, newly remodeled, extra large 2 bdrm basement

Beautiful home in a very nice, quiet neighborhood. Close to downtown Ashland (3 miles) and I-64 (5 miles). This is a full size newly remodeled basement with it's own outside entrance. Great host and great setting. Access to the beautiful back yard, kids gym, gazebo, firepit, grill and covered patio. The basement has large windows in the bedrooms and queen beds. Located 8 minutes from King’s Daughters Hospital and 30 minutes from Huntington, WV hospitals. Long term travel workers welcome.

Top guest favorite

A quaint cottage is set against a backdrop of lush greenery and rolling hills. The structure features a porch with rocking chairs, and large windows provide natural light. Towering trees surround the property, contributing to the serene atmosphere.

Farm stay in Morehead

5 out of 5 average rating, 21 reviews

Morehead Farm Cottage

This memorable place is anything but ordinary. Nestled at the front of our family farm, enjoy a cup of coffee on the front porch, or catch the best sunsets in Kentucky. This one bedroom cottage includes a sleeping loft, full bath with laundry, and a full sized kitchen. Stretch your legs exploring the vineyard or fishing the ponds next to the cottage. We are a working farm with chickens, gardens, and the farm dogs. We are just 4 miles from I-64 and 8 miles from Morehead State University Campus.

Superhost

A rustic wooden cabin is situated among trees, featuring a spacious deck and an American flag displayed on the front. The structure exhibits a combination of log and modern elements, complemented by large windows that allow natural light to fill the interior.

Cabin in Olive Hill

4.94 out of 5 average rating, 159 reviews

Cliffside Properties / Carter Caves Cabin Rental

Perched on the edge of the canyon at the entrance to Carter Caves State Park, our 3-story cabin easily sleeps 10. On our twenty acre preserve, there are 5 cave entrances and two caves that open into the State Park gorge, with many box canyons and waterfalls to explore. Whether you're enjoying the State Park's massive natural bridges, cave tours, horseback riding, swimming, fishing or kayaking on Smoky Lake or Tygarts Creek, our Cliffside Cabin rental is a great place to relax and explore.

Top guest favorite

A small wooden cabin features a light wooden exterior with a green roof. A front porch is accessed by three steps, providing a welcoming entrance. One window is visible on either side of the door, surrounded by grassy areas and trees in the background.

Cabin in Carter County

4.98 out of 5 average rating, 101 reviews

Cabin at Cabin Creek Campground

Private cabin located in campground close to bathhouse. A/C and electric fireplace. Porch swing, fire ring, & picnic table for your outside enjoyment. Queen size bed with full size bed in loft overhead. Microwave & small refrigerator. Dining table with 3 benches. Comfortable sitting chair with footstool. Fishing included in our 12-acre lake. Walking path runs the length of the campground. Bring bed linens (sleeping bag or blanket/sheet) & pillow, bath linens (towels/washcloths).

Top guest favorite

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, 120 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 favorite

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, 100 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 favorite

A newly renovated home is positioned on a green, spacious lawn with manicured grass. The structure features a gable roof and a covered front porch, providing a welcoming entrance. Lush trees and a gentle slope are visible in the background.

Home in Olive Hill

5 out of 5 average rating, 23 reviews

A Grayson Lake Getaway

This quaint newly renovated home is waiting for you! Come hike, boat, kayak, fish or just relax on the covered patio. Located just one minute from Caney boat ramp, Grayson lake. 10 miles from Grayson Lake Marina. 9 miles from Hidden Cove Golf Course and campground. 5 miles from Laurel Gorge. 21 miles from Carter Caves State Park. Property has a large yard and can easily get a boat in and out of the driveway. Come visit! I look forward to accommodating you!

Top guest favorite

A charming cabin is nestled among the trees, featuring a wrap-around porch with seating. The wood exterior and sloped roof complement the natural surroundings. The gravel path leads to the entrance, enhancing the inviting atmosphere of the woodland retreat.

Cabin in Wellington

4.97 out of 5 average rating, 127 reviews

Luxe Glamping A-Frame Cabin-Porch-Hammock-Dogs ok

Your forest cabin awaits at Nestled Inn cabin, relax, unplug, unwind, and experience KY’s countless natural resources. Experience the best of Daniel Boone National Forest, Cave Run Lake and Red River Gorge. Our 2 bedroom 1.5 bath cabin is fully equipped cabin with all the amenities, smart TV, Wifi and more. Escape to nature in style, but please remember we are in the woods that may mean you will see wildlife and the occasional insect or bug.

Top guest favorite

A rustic, two-story red cabin is situated on a grassy hill, surrounded by lush green trees. The home's balconies are visible, offering a sense of elevation. A misty atmosphere adds a serene quality to the landscape, enhancing the natural beauty of the setting.

Home in Grayson

4.97 out of 5 average rating, 34 reviews

Getaway to Taylor View Acres

Forget your worries in this spacious and serene space. Enjoy a breathtaking view from two private balconies. The entire home featuring 3,500 sq ft is yours to enjoy. The home features 3 bedrooms and 3 bathrooms with a downstairs, fully-furnished basement. Conveniently located about 10 minutes from the 64 freeway and downtown Grayson. Located just a short drive from Carter Caves, Grayson Lake, Greenbo Lake, Sandy's Gaming and Malibu Jacks.

Superhost

The exterior of the cottage features a welcoming porch with two comfortable chairs positioned on either side of a decorative door. The roof is metal and dark, and colorful flower pots add charm to the grassy yard.

Home in Olive Hill

4.89 out of 5 average rating, 38 reviews

The Red Rose Cottage

Come on in! Relax, unwind, enjoy! This quaint trail town cottage is a perfect stay for a couple of nights or a few weeks. Come fish, hike or take it easy like Sunday morning! Right off of interstate 64, Just a few miles from Carter Caves State Park, 20 miles to Cave Run Lake, 13 miles to Grayson Lake. If you’re just traveling through, stop and stay at our cozy cottage instead of an interstate hotel! We look forward to accommodating you!

Guest favorite

The exterior of a cozy cabin is shown, featuring a wooden porch with dual rocking chairs. The building is clad in a combination of rustic red and brown siding, complemented by a simple white door and multiple windows providing natural light.

Cabin in Salt Lick

4.91 out of 5 average rating, 151 reviews

The Cedar Shack

Enjoy Cave Run Lake or take a short drive (21ish miles) to Red River Gorge from our Tiny Cabin. Our Cedar Shack is a 12ft x 28ft with a 4ft porch, equipped with dual rocking chairs. The Cedar Shack is appropriately named as it is finished fully is cedar from floor to ceiling. Pets are welcome in most instances but they must be included in the guest list and there is a fee. No exceptions.