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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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.
Cabin in Wellington
4.99 out of 5 average rating, 159 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, 124 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 hot tub is positioned on a covered deck, overlooking lush green hills and treetops. The water is bubbling, inviting relaxation while the natural landscape offers a serene backdrop. Sunlight filters through the trees, creating a peaceful ambiance.
Cabin in Frenchburg
5 out of 5 average rating, 122 reviews

The Bluff on Amos Amazing Views!

This unique place has a style all its own. Centrally located between Red River Gorge and Cave Run Lake. Enjoy a hike at the gorge or a day at the lake. Come back enjoy soaking in the hot tub and take in the views!!! This spacious one bedroom one bath with tub/ shower is the perfect place for a getaway. It is equipped with full size appliances and everything you need to prepare a meal. The outdoor fire pit and charcoal grill are perfect for any outdoor cooking and relaxing!!!

Guest favorite
The rustic black cabin features a steeply pitched roof and is surrounded by greenery. A simple pathway leads to the entrance, with a deck visible on one side. Neatly trimmed bushes and trees enhance the outdoor space, providing a sense of privacy.
Cabin in Wellington
4.9 out of 5 average rating, 173 reviews

Cheerful 3 Bed Cabin Firepit Hot Tub Cave Run Lake

Welcome to Black Bear Cabin. Overlooking the beautiful Daniel Boone National Forest and very close to Cave Run Lake and many popular hiking trails This is our families home away from home. We love this spacious and peaceful getaway and hope you do as well. This Cabin is a Rustic 3 Bedroom w/ Loft Area. It has 2 full bathrooms. Our kitchen is fully equipped for cooking meals. On the deck is a relaxing hot tub and grill. In the yard is a firepit with adirondack chairs.

Top guest favorite
Cabin in Flemingsburg
5 out of 5 average rating, 24 reviews

Sugar Loaf Retreat

WE ACCEPT 1 NIGHT STAYS! Welcome to Sugar Loaf Retreat where you can relax at this unique and tranquil getaway. Located on a 45 acre farm, this outstanding A frame cabin is sure to deliver what you are seeking- quiet, relaxing experiences, where you wake up to nature right outside the door! Autumn Blaze Comfort is on the same property and can be booked at the same time subject to availability. This suite offers 2 bedrooms and a full kitchen and full bathroom and living area.

Top guest favorite
A large converted barn with a striking red exterior is set against a vibrant sunset sky. The building features multiple windows and a spacious porch, while a grassy yard surrounds the property. Telephone poles and fencing are visible, enhancing the rural landscape.
Home in Hillsboro
4.94 out of 5 average rating, 67 reviews

HUGE Country Get Away-RELAX!

Huge converted barn! Unique rustic stay, the house barn is as big as two houses in one! It has two separate living areas, two kitchens, and multiple bedrooms! There is also a very large front yard, a concrete drive with ample parking, and a nice front porch to sit on. The listing is co-managed by me and my parents. This is my parents' (2 people) main home, so it is normally lived in, but way too large not to share with others! You will have the entire space when rented!

Top guest favorite
The farmhouse exterior features a light-colored facade with white shutters and a welcoming front porch. A curved pathway leads to the entrance, surrounded by a well-maintained lawn and neatly trimmed bushes. Two chairs are positioned on the porch, inviting relaxation.
Farm stay in Ewing
4.99 out of 5 average rating, 190 reviews

Haymark Farmhouse: cozy, country memories

Welcome to Haymark Farmhouse, built in 1907. Relax in front of the fireplace with electric logs, play games (provided), and cook in the well-supplied kitchen or on the gas grill out back. Enjoy the outdoor fire pit (wood provided) and the lighted outdoor patio area and table for eight. Explore our 275 acre farm! Check out our farm animals, take a hike along the creek, catch a fish in the pond, hunt (message us for rates), watch a sunset ...Enjoy your time at Haymark Farm.

Guest favorite
The exterior of Shady Pines Inn is visible, featuring a one-story brick structure surrounded by lush greenery. Sunlight filters through the leaves of trees, highlighting the manicured lawn and a wooden storage unit positioned near the side of the house.
Home in Morehead
4.92 out of 5 average rating, 207 reviews

Kick off summer with June specials at Shady Pines

Shady Pines Inn is a vacation rental located .7 mile from Exit 133 off interstate 64. Ten minutes to Cave Run Lake and Morehead. 3 bedrooms, king, queen & 2 twin beds, 2 new cots with memory foam toppers. 1.5 baths,living room with 2 couches & 3 chairs. Full kitchen, accessible tub/shower. Snacks, cereal/granola bars, oatmeal, donuts, bread, bagels, local eggs, coffee, tea. Any combination of these items will be offered.

Top guest favorite
A rustic cabin is set against a backdrop of a colorful sunset, showcasing its wooden exterior and a red metal roof. Surrounding the cabin, a fire pit is framed by seating made of tree stumps, creating an inviting outdoor space for gatherings.
Cabin in Stanton
4.98 out of 5 average rating, 159 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.

Top guest favorite
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, 46 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!

Superhost
A secluded cabin features a rustic wooden exterior with a green metal roof. The wraparound porch includes a set of wooden steps leading to the main entrance, surrounded by a natural landscape of trees and ground covered in light snow.
Home in Mayslick
5 out of 5 average rating, 10 reviews

Kentucky Cabin Getaway w/ Loft Sleeping

Wildlife Cabin is a charming rental located in Mayslick, KY. Sparkling clean and full of charm, you'll find this the perfect spot for your vacation. On the main floor, you'll find a kitchen equipped with the basics for cooking, a beautiful living area with a fireplace, a bedroom with a queen sized bed, and a full bathroom. Upstairs is a loft with a twin over full bunk bed and another twin bed.

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
4.92 out of 5 average rating, 159 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.

Popular amenities for Hillsboro vacation rentals

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