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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
An A-frame cabin is surrounded by trees showcasing autumn foliage. A spacious deck extends from the entrance with seating available. The dark exterior is contrasted by bright wooden accents and a welcoming front door, completing the rustic appearance within the tranquil forest setting.
Cabin in Wellington
4.8 out of 5 average rating, 142 reviews

Secluded Cave Run Red River Gorge Cabin

This A frame cabin is a unique 2.5 acre getaway that is nestled in the Daniel Boone National Forest just minutes away from Cave Run Lake and Broke Leg Falls. It is within a 20-30 minute drive from Red River Gorge and Morehead Kentucky and 45 minutes from Carter Caves. If you love the outdoors there is plenty to keep you busy, swimming, kayaking, boating, biking, fishing, golfing, hiking, caving, and rock climbing. Firepit out back if you want to roast smores and tell a scary ghost story.

Top guest favorite
Home in Manchester
4.94 out of 5 average rating, 124 reviews

River Front Oasis Relax and Unwind w/ Hot Tub

Welcome to our fully renovated rustic retreat nestled on the scenic Ohio River. This 3 bed, 2 bath house is located on 10 acres of breathtaking riverfront property. Enjoy fishing and boating right from your doorstep, then unwind in the inviting hot tub. Gather around the cozy fire pit as you take in the tranquil views. Perfect for nature lovers seeking an unforgettable getaway.***Guest and pet number affects pricing. Ensure you have the correct number of guests and pets before booking.

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, 148 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, 115 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, 108 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
Cabin in Flemingsburg
5 out of 5 average rating, 10 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, 180 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 sitting 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 cozy interior showcases a white sofa with decorative pillows set against a wood-paneled wall. A small dining table and chair are positioned nearby, illuminated by a soft lamp. A ceiling fan circulates air above, while a television is mounted on the wall.
Home in Salt Lick
5 out of 5 average rating, 68 reviews

Clear Creek Get Away

Located at the entrance of Cave Run Lake. Close to The Gorge, White sulphur atv& horse trails, Clear Creek lake ,hiking trails , Zilpo and leatherwood boat ramps all within minutes away. Natural bridge is only a 45 minute drive away and many other things to do close by also a short drive to the other side of cave run lake. This new tiny house has plenty of room inside and out. Sits along the Salt Lick Creek. Enjoy campfires in the evenings and relax

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, 37 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 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, 157 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 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, 345 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 vacation rentals

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