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, 156 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, 121 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
Cabin in Flemingsburg
5 out of 5 average rating, 18 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
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, 186 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 cute 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.

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!

Guest favorite
An outdoor fire pit is surrounded by several wooden chairs, set on a lush green lawn. The lodge's exterior features multiple flags and is visible in the background against a vibrant sunset sky with soft purple and pink hues.
Home in Aberdeen
4.96 out of 5 average rating, 141 reviews

Minton Lodge - Relax, Rewind, Enjoy!

Privacy and peacefulness is what you'll experience at the beautiful Minton Lodge, a service offered by the Josh Minton Foundation. 4 bedroom and 2 full baths in a very remote location on a 49 acre wooded property . Wrap around porch, hot tub, fire pit, gas grill, smoker, and a wood stove in large living room. Walking trails with plenty of wildlife. Wifi, DirecTV, DVD player and two LCD TV's. 10 minutes from the Ohio River and Maysville, Kentucky.

Top guest favorite
An outdoor firepit area is surrounded by four black Adirondack chairs, placed on a bed of small gravel stones. Decorative lights are strung overhead, creating a cozy atmosphere. The horizon displays a picturesque sunset over a lush green lawn, framed by trees and an open field.
Home in Flemingsburg
5 out of 5 average rating, 45 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.

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, 204 reviews

Shady Pines Sheltowee MSU Cave Run

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
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, 38 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!

Top guest favorite
A welcoming living space features hardwood flooring and soft gray walls. A comfortable sofa and patterned armchairs are arranged around a rustic coffee table. Ceiling fans provide ventilation, while large glass doors open to a view of the expansive yard.
Farm stay in Carlisle
4.99 out of 5 average rating, 171 reviews

Hilltop Retreat at Wendt’s Wildlife Adventure

Take it easy at this unique and tranquil getaway. Newly remodeled home on a 125 acre farm that is home to Kentucky’s newest wildlife park & Daniel Boone’s last home in Kentucky. Expansive views, and a visit to Wendt’s Wildlife Adventure (open seasonally), which is owned & operated by your hosts, are sure to give you just the right amount of rest & adventure that you are seeking.

Guest favorite
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, 347 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!!!

Guest favorite
The cabin is nestled among vibrant autumn trees, with a large wooden deck extending from its front. A pathway leads to the entrance, which is framed by fallen leaves. The warm hues of the surroundings provide a serene and cozy retreat atmosphere.
Cabin in Frenchburg
4.92 out of 5 average rating, 109 reviews

Hygge Nock at Lush Hollow

Nestled perfectly on a ridge of our 40-acre property, minutes from Cave Run Lake and 25 miles from Red River Gorge, this Scandinavian-themed cabin is the perfect ridge-top retreat. Enjoy nearby hiking, boating, and golfing. Relax with a hot tub, pellet grill, and cozy fire pits. Explore quaint towns, state forests, and local markets. Your ideal super cozy, secluded getaway awaits!

Popular amenities for Hillsboro vacation rentals

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