Holiday rentals with outdoor seating in Bourbon County

NEW Lilley Manor: Paris Elegance & Antique Comfort

Step into history while enjoying cozy comfort in this private suite of the 1860 Lilley Manor, the very first house built on Duncan Avenue. With original walnut and cherry floors, antique 1800s furniture, and a touch of European charm, this is where Kentucky history meets modern hospitality. Perfect for couples, travelers, and history buffs, this private suite offers 1 bedroom, 1 bathroom, kitchenette, and parlor seating - all completely closed off from the main house with a secure keypad entry.

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.

The Parsonage | Grand 19th Century 4 Bdrm Home

Step into timeless elegance at The Parsonage, a beautifully restored 19th-century home overlooking Millersburg’s historic town square. Blending heritage and hospitality, this home captures the charm of a bygone era with soaring ceilings, original woodwork, and period furnishings, paired with the comfort and convenience of modern living. Thoughtful details and inviting spaces encourage you to slow down and savour your stay, with downtown Millersburg just steps from the door.

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.

Historic Mt Lebanon, The Governor’s Estate

Experience Kentucky history and scenic farm-living at historic Mt. Lebanon while being nestled in the middle of thoroughbred and bourbon country. You will be within 30 minute drive to Keeneland Race Track, The Kentucky Horse Park, bourbon distilleries and the University of Kentucky. You are also just minutes from the well-known Claiborne Farms (Home to Secretariat) and the historical Runnymede Farm.

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.

The Honey Hut, Think of “ On Golden Pond"

The perfect honeymoon or family-friendly quality getaway spot, nestled in the quiet countryside of Mt. Sterling, KY - with a beautiful lake just steps from your back porch. Take your family or friends canoeing, paddle-boating, fishing. End your stay with a campfire in the fire pit to make this an unforgettable getaway.