Vacation rentals in Hillsboro

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Top-rated vacation rentals in Hillsboro

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

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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 homes in Flemingsburg
4.92 out of 5 average rating, 177 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 favourite
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, 31 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.

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, 112 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

Superhost
An inviting outdoor porch area is framed by wooden railings and surrounded by greenery. The structure features a rustic wooden facade, with large windows allowing natural light to illuminate the space. A sitting area is visible, providing a tranquil spot to relax.
Cabin in Wellington
4.82 out of 5 average rating, 148 reviews

The Haven@Cave Run Lake

Kick back and relax in this calm, stylish space. Surrounded by The Daniel Boone National Forest, “The Haven” is your place to relax, hike, fish, boat, or climb. Only 5 minutes to Long Bow Marina or 15 minutes to Scott’s Creek Marina. Cave Run Lake awaits. Beautiful Morehead and Morehead State University is 20 minutes away. World class climbing in the Red River Gorge is just under an hour away. Blazing fast fiber internet allows you to play, work, relax.

Top guest favourite
Home in Flemingsburg
5 out of 5 average rating, 29 reviews

Red Bird Estates

Escape to our cozy, remodeled farmhouse—perfect for couples, families, or friends. Decorated just in time for Christmas. Enjoy 3 comfy bedrooms, a clean bathroom, a fully stocked kitchen, and a game-friendly living room. Relax on the back deck with peaceful views, unwind by the firepit, or swing on the tree swing or relax in the hammock. Whether you're here to rest or explore, this charming country home is the perfect getaway.

Top guest favourite
The exterior of a historic distillery building from the 1860s is shown, featuring exposed brick walls and a neatly maintained façade. Two stories of windows are framed by wooden accents, and an inviting entrance is flanked by stone pillars, contributing to the building's historical charm.
Home in Flemingsburg
5 out of 5 average rating, 28 reviews

1860's building brought to life

This 1860's original distillery building will take you back in time with it's spacious yet cozy areas to relax and enjoy. Exposed brick exterior walls surround you while belt driven fans keep you cool as you relax and read a good book, play some games with the kids or enjoy a nice dinner at one of the many seating areas. We hope you enjoy your stay in our home as much as we enjoyed living here!

Guest favourite
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
4.92 out of 5 average rating, 156 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.

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, 342 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
A spacious cabin with a warm brown exterior is surrounded by bare trees. A set of wooden stairs leads to a welcoming front porch, which is complemented by an outdoor seating area. The structure features a mix of log and stone materials.
Cabin in Morehead
4.96 out of 5 average rating, 210 reviews

Morehead Cabin by the Lake

A relaxing space that can accommodate up to six people. This cabin is 3 min from Cave Run Lake and close to downtown Morehead and Morehead State University (15 min). Tucked up on a hillside surrounded by oak trees, enjoy the front porch and comfortable accommodations for the perfect, calming getaway. Great for work or play, this cabin has it all.

Guest favourite
The cabin's covered front porch features two wicker chairs and a small table, surrounded by greenery. Two green doors with arched windows serve as the entrance, and a pathway leads to the gravel parking area. Outdoor lighting accents the inviting space.
Guesthouse in Vanceburg
4.92 out of 5 average rating, 146 reviews

Boulder Brook Cabin

Wonderful cozy guest cabin in the woods. Knotty pine living space with outdoor elements throughout. Open concept with beds/living room/kitchen all sharing the same space. Full stocked kitchen with Kuerig coffee bar ready to start your day off right! Covered front porch for sitting and enjoying the views. Parking at front door.

Top guest favourite
A spacious living area features a brown leather sofa paired with two white armchairs. A wooden coffee table sits on a colorful area rug. A flat-screen TV is mounted on the wall, with natural light streaming through the windows adorned with patterned curtains.
Guesthouse in Morehead
4.98 out of 5 average rating, 136 reviews

Quiet 2BR Between Hospital and Morehead State

Spacious 1100 square foot guest house will give you a cozy place to rest before exploring our downtown. Check us out on insta! @thehaven.airbnb 5 minute walk to campus. 8 minute walk to the hospital. 5 minute walk to main street. 17 minute drive to the lake (space to park boat/trailer off street).

Top guest favourite
A spacious studio retreat features a king bed with white linens, accompanied by a modern gray sofa. Natural light enters through large windows, while a stylish black accent wall adds depth. A small glass table and potted plant complete the inviting ambiance.
Home in Morehead
4.96 out of 5 average rating, 70 reviews

Luxury studio, downtown Morehead, clean & new

Brand new, beautifully finished and furnished studio retreat in downtown Morehead! Exactly 1 mile to the campus of Morehead State University and only a few blocks from UK St. Claire Hospital. Large custom tile shower, fully stocked kitchen, fireplace, washer and dryer in unit, comfy king bed!

Popular amenities for Hillsboro vacation rentals

  1. Airbnb
  2. United States
  3. Kentucky
  4. Fleming County
  5. Hillsboro