Vacation rentals in Olive Hill

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Top-rated vacation rentals in Olive Hill

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Guest favorite

A small cabin features wood siding and a welcoming porch with wooden railing. The entrance is accessed via steps leading to the porch, surrounded by greenery and trees, enhancing the cabin's natural setting.

Cabin in Morehead

4.94 out of 5 average rating, 16 reviews

Rustic Cabin Charm

Located (5 miles) from Cave Run Lake, have a great night’s rest after a fun day on the Sheltowee Trace National Trail, Lockegee Rock, Amburgey Rock or at Dirt Nasty ATV Park (within 1-2 miles). We offer a full bed, full bath, kitchenette sink, coffee pot, towels, sheets, quilt and fire pit (starter wood included). Bring your lawn chairs and supplies for s'mores for a relaxing evening by the fire. Ample boat parking, if needed. Approximately five miles from town, ten miles to big box stores.

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.

Superhost

The exterior of a modern tiny home is showcased, featuring a spacious wooden deck with railings. A large grassy area surrounds the home, complemented by a clear blue sky. A dog relaxes in the foreground, contributing to the tranquil environment.

Tiny home in Flemingsburg

4.92 out of 5 average rating, 173 reviews

The Concord - Enjoy the Vineyard Views

Experience tiny home living without giving up the comforts of home. Kick back and relax in this modern 'spacious' tiny home loaded with the most up to date amenities - and Vineyard views right out your front door! This one bedroom home offers additional space for the family and kids with an upstairs loft and a roomy living area. Added bonus - you're a short walk to our family owned winery and restaurant! Plus- many historic attractions just a short drive away. Come enjoy the luxury tiny life.

Top guest favorite

A welcoming porch features a wooden deck with a checkered tablecloth on a table, surrounded by chairs. Two patterned rugs define the seating area, while decorative elements like flowers and a small table with a lamp add character to the space.

Home in Morehead

4.91 out of 5 average rating, 70 reviews

Home

Off the beat and path. Relax with the whole family at this peaceful place to stay The home is located in a small VERY country neighborhood We are NOT NEAR A TOWN or I64 We are 1.8 miles from Hogtown Hill(Elliottville) 11 MILES TO DOWNTOWN MOREHEAD where MSU is located. Poppy mountain is 11 miles Cave Run 24 Our place is a 1972 refurbished manufactured home with some mid-century furnishings and decor and some updates. There is also a large addition on the trailer which makes for a lot more space

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, 24 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.

Guest favorite

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, 162 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, 105 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 corner of the room features a wooden dresser and a small desk with a chair, illuminated by a lamp. A decorative flower arrangement rests on the dresser. Textured wall art is displayed above the desk, creating a cozy atmosphere.

Farm stay in Morehead

4.97 out of 5 average rating, 67 reviews

Unique & Exciting

Approx 6 miles from I64. check into this unique guest house, facing the woods, you won’t be disappointed in the location or the atmosphere ,Relax on the porch or visit the goats at the farm, march is birthing season, come down the store and listen to the beekeepers discuss bee care, we also have a indoor beehive for viewing without touching (seasonally). Make us your next reservation, we look forward to seeing you. This property has 1 full size bed and one sofa fold out twin.

Top guest favorite

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, 150 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

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, 25 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, 37 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.