Holiday rentals with outdoor seating in Bourbon County

1790s cottage in Millersburg

Le Ménil is a circa 1790 cottage on Main Street in Millersburg, KY. The early federal house is warm, comfortable, and inviting. Recently restored by the host, Le Ménil is full of antique furniture to compliment the period of its construction. Located on Main St. in Millersburg, it is conveniently located within walking and driving distance of Mustard Seed and Maplewood Estate and Barn. Proceeds from this listing go towards the preservation of this landmark. Ask about extended stay discounts.

Misfit Farm

Need to get away? Misfit Farm sits 700’ from the road, offers 3 bedrooms, a spacious kitchen & dining area for family meals and a theatre room to enjoy. 2 bedrooms have queen beds and 1 has a twin daybed with a trundle underneath. After a long day you can enjoy the 10' x70' covered porch while watching the sunset. 6 guests can make this a home base for visiting local farms, horse events and bourbon trails. We are just 40 minutes from Lexington where you can enjoy Rupp Arena & Keeneland.

Authentic Hilltop Log Cabin, 360° Views, Sleeps 15

Rustic Appalachian log cabin located in the countryside of Cynthiana, Ky. Come experience the serenity of the sunrise from the wrap-around porch while sipping your coffee in an Amish-built glider chair. Situated on 25 rolling acres, scenic views can be taken in from all sides. Fishing is available from a stocked pond where deer come to drink in the evening. The cabin sleeps 15 comfortably or 2 for a romantic retreat. Turn off the beaten path and experience the tranquility of the country.

The Cottage at Hickory Manor

The cottage at Hickory Manor offers incredible views, a perfect location, and a modern set up to insure your stay is perfect. Surrounded on both sides by horse farms, experience a true KY visit . House consists of a large open floor plan, master bedroom with attached full bath, a queen room and 3rd bedroom with 2 twin beds. An air mattress is available for 2. Conveniently located 13 miles to the KY Horse Park, 14 miles to downtown Lexington city center, 19 miles to Bluegrass Airport

Peaceful Retreat on the TB horse farm

Small one bedroom apartment connected to the horse barn. All on the first floor , the only apartment . Apartment with living room, 1 bedroom, full bath and kitchenette (microwave, refrigerator/freezer with ice maker, Keurig, toaster oven) NO STOVE, NO OVEN. We will provide individual water, cocoa, tea, several flavored coffees and creamers. The owners live on the property. Children under 18 are not allowed, It is a working farm/Veterinarian clinic not suitable for children.

Private Carriage house in KY

Kick back and relax in this calm, stylish space. Your own private retreat for you and your pets, a 2 Bedroom / 1 Bath carriage house, with an in-ground heated pool (Apr - Oct), firepit and plenty of space to unwind in the country! Convenient location in horse country that is within 20 miles from Lexington (LEX), Keeneland, UK, Kentucky Horse Park, Horse Farm Tours, Bourbon / Distillery tours, or enjoy the charm of Paris, KY. Come and let us show you Southern hospitality!

Scenic Stillwater Retreat

Discover the beauty of Thoroughbred horse country at its finest in this custom-built artisan retreat. Spend your days canoeing or fishing on the private pond, exploring 27 scenic acres, and unwinding in the waterfront gazebo or sunroom. Enjoy elegant comfort with peaceful workspaces, indoor and outdoor games, and evenings by the fire pit. A refined yet family-friendly getaway—just a short drive to the Ark Encounter, Bourbon Trail, Keeneland, Horse Park, UK games, and more!

Carriage House

Unwind with the spacious area this apartment has to offer. It is located on a working horse farm above the shop, in the renowned Bluegrass region of Ky. At Houstondale you can stroll to the barn and visit the horses or hide away in your space and relax. The KY Horse Park is a 22 minute drive, Lexington is 25 minutes and you are 30 minutes from horse racing at Keeneland Race Track. Even with the remote feel you are only 1 mile from Walmart, shops, and downtown Paris.

Horse & Flower Farm Barn Loft

Enjoy peace and quiet in the countryside surrounded by Stoner Creek. Old Bridge Farm is a horse farm and also the home of Blooms of Bourbon County which is a flower, fruit and vegetable grower utilizing organic growing practices. Our 100 year old tobacco barn has been converted into a stable with a large rustic loft above with all of the conveniences of home. We're off the beaten path on a very quiet road in the middle of horse country. Come...relax, escape, recharge.

Historical 1812 Home | Chef's Kitchen, Laundry, AC

Step into a piece of history at The Boarding House, a carefully restored 1812 home blending timeless elegance with modern comfort. Perfectly situated at Main and 9th Streets in Millersburg’s historic district, this stately residence features a grand front porch, a welcoming foyer with a curved staircase, original hardwood floors, a chef’s kitchen, cozy fireplaces, and serene private suites. With lots of space, it's ideal for larger families and groups.

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.

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.