Vacation rentals in Hillsboro

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Top-rated vacation rentals in Hillsboro

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Top guest favorite

Farm stay in Ewing

4.99 out of 5 average rating, 170 reviews

Haymark Farmhouse: cozy & clean, with outdoor fun!

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! Pet our cute farm animals, take a hike along the creek, catch a fish in the pond, hunt (message us for rates), watch a sunset ... If you need room for more folks, check out Thomas Road House.

Superhost

Tiny home in Flemingsburg

4.92 out of 5 average rating, 173 reviews

The Concord - Enjoy the Vineyard Views

Experience tiny home living without giving up the comforts of home. Kick back and relax in this modern 'spacious' tiny home loaded with the most up to date amenities - and Vineyard views right out your front door! This one bedroom home offers additional space for the family and kids with an upstairs loft and a roomy living area. Added bonus - you're a short walk to our family owned winery and restaurant! Plus- many historic attractions just a short drive away. Come enjoy the luxury tiny life.

Top guest favorite

Home in Wellington

4.99 out of 5 average rating, 125 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

Home in Morehead

5 out of 5 average rating, 104 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

Home in Hillsboro

4.94 out of 5 average rating, 63 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

Farm stay in Morehead

4.97 out of 5 average rating, 70 reviews

Unique & Exciting

Approx 6 miles from I64. check into this unique guest house, facing the woods, you won’t be disappointed in the location or the atmosphere ,Relax on the porch or visit the goats at the farm, march is birthing season, come down the store and listen to the beekeepers discuss bee care, we also have a indoor beehive for viewing without touching (seasonally). Make us your next reservation, we look forward to seeing you. This property has 1 full size bed and one sofa fold out twin.

Top guest favorite

Home in Winchester

4.91 out of 5 average rating, 854 reviews

Cozy Cottage

Sweet little cottage within walking distance of historic downtown Winchester. Open floor plan, 500 square feet of coziness! Queen size bed, kitchen, living room, dining all in one place. We’re a working farm on the edge of the city limits in an older non-gentrified neighborhood. Surrounded by the Kentucky Horse Park, Keeneland, Rupp Arena, Fort Boonesboro, Red River Gorge and the Kentucky Bourbon Trail. Easy access to I-64, I-75, and Mountain Parkway - gateway to Appalachia.

Top guest favorite

Cabin in Wellington

4.97 out of 5 average rating, 144 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 favorite

Home in Flemingsburg

5 out of 5 average rating, 21 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!

Guest favorite

Cabin in Salt Lick

4.91 out of 5 average rating, 152 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.

Top guest favorite

Farm stay in Carlisle

4.99 out of 5 average rating, 165 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.

Top guest favorite

Home in Flemingsburg

4.98 out of 5 average rating, 335 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!!!