Holiday rentals in Hillsboro

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Top-rated holiday rentals in Hillsboro

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

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Top guest favourite
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 favourite
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 favourite
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 favourite
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 favourite
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 favourite
Home in Wallingford
5 out of 5 average rating, 12 reviews

Spacious Lodge w/ Fire Pit & Hot Tub

Wildcat Lodge is a beautiful home tucked away in the countryside, just 10 minutes from I-64 in Morehead, KY. Beautifully furnished and with much attention to detail, you'll love all our home offers. There is a spacious eat-in kitchen equipped with the basics for cooking, a cozy living room, a master suite with a king bed and attached bath, two more bedrooms with king beds, and one more with a queen bed. There is also another full bathroom and a laundry room.

Top guest favourite
A serene waterfall flows down a rocky cliff, surrounded by lush greenery and tall trees. The water creates a gentle cascade, while smaller streams can be seen nearby. The earthy ground is covered with fallen leaves and ferns, enhancing the natural ambiance.
Cabin in Wellington
4.97 out of 5 average rating, 164 reviews

Hideaway Falls - cabin with private waterfall view

Unwind at this peaceful and private oasis in the heart of Daniel Boone National Forest. Enjoy relaxing and exploring on and around the property or take a short drive to experience the best of Red River Gorge and Cave Run Lake. Take in the waterfall view on the front porch while you enjoy your morning coffee or be lulled to sleep by the sounds of cascading water at night. Perfect for a romantic getaway or a weekend with friends.

Top guest favourite
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, 53 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 favourite
A stone fire pit is situated in the foreground, featuring a glowing flame surrounded by scattered leaves. In the background, the cabin is illuminated warmly, highlighting its deck and inviting outdoor seating. The serene landscape is filled with trees, creating a peaceful atmosphere.
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 favourite
A spacious kitchen area features a large wooden island surrounded by high-backed stools. Exposed brick walls add character, while a light fixture with multiple bulbs hangs overhead. Natural light filters through two windows adorned with shutters, illuminating the warm tones of the wooden flooring.
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!

Top guest favourite
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, 173 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 favourite
Home in Flemingsburg
4.98 out of 5 average rating, 353 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!!!

Popular amenities for Hillsboro holiday rentals

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