Vacation rentals in Hillsboro

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.

Location · Value · Nearby

Western Charm

A one bedroom unit in a converted tobacco barn, is just what the weekend ordered! Located just fifteen minutes from Morehead, Ky. and I64. This cozy home away from home, will have you feeling relaxed & rested. It’s true that the pics are adorable, & HONEY please believe me when I tell you, she really is THAT cute in person! She will have you leaving here thinking you need a new pair of boots, y’all!! You will love the fact that everything is ALWAYS clean, neat and tidy, here! (No pet unit)

Location · Family · Condition

The Cove at Cave Run

Discover serenity near Cave Run Lake at our charming cottage in Morehead, KY! Ideal for nature lovers and outdoor enthusiasts, our cozy retreat offers modern comforts and is located only minutes to Scotts Creek Marina. With 2 queen beds, a fully equipped kitchen, and room for your boat trailer, it's the perfect base for your Kentucky adventure. Explore hiking trails, water sports, and local attractions, then unwind in comfort. Book your stay now for a fun getaway at The Cove at Cave Run!

Value · Location · Parking

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

Value · Family · Amenities

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.

Value · Family · Quiet

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!

Location · Family · View

Studio, clean, new, fireplace, Downtown Morehead

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! If this is booked, check out our other listing, right next door! It has blue shiplap behind the bed in the listing photo! Or contact me and I’ll set you up! :)

Location · Value · Walkability

The Nest at Lush Hollow

Calling all love birds! The Nest is a romantic treetop A-frame perched on a ridge with stunning views from every room. Floor-to-ceiling windows, a wraparound deck, and a hot soaking tub for two set the scene. Rest, reconnect, then explore nearby hiking, boat docks, horse camps, golf, state forests, markets, and more. Just minutes from Cave Run Lake and a scenic 25-mile drive to Red River Gorge—your dreamy woodland escape awaits!

Location · Air conditioning · Checkout

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.

Location · Family · Indoor spaces

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!

Value · Location · Kitchen

Peaceful Kentucky Ranch

Unplug and unwind at our peaceful 40-acre Kentucky ranch. This spacious 3BR, 2.5BA home offers views of Texas Longhorns and alpacas, plus modern comforts in a serene country setting. Relax on the porch, gather by the fire pit, and explore nearby attractions like Buffalo Trace Distillery, Kentucky Horse Park, hiking trails, and golf. Perfect for families, couples, or Bourbon Trail adventurers.

Family · Location · Kitchen

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.

Location · Value · View