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.

1791 Cabin on Historic Horse Farm

This rare 1791 log cabin is located on Houstondale Farm, a working horse farm in the renowned Bluegrass region of Ky. You can stroll to the barn and visit the horses or enjoy the peace and quiet before relaxing at the pool, complete with a grill and outdoor dining area. It is a scenic 22 minute drive from the Ky Horse Park, 25 minutes from Lexington, and 30 minutes from Keeneland Race Track. Even with the remote feel of the farm you will only be a mile from Walmart, shops & downtown Paris.

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.

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.

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.

Scenic Stillwater Retreat

Savor the wonder and beauty in the heart of Thoroughbred horse country in this one-of-a-kind, custom-built home. Make memories canoeing and fishing, exploring the 27-acre farm while viewing surrounding horse farms, and relaxing in the waterfront gazebo and sunroom. Enjoy indoor/outdoor games, quiet workspaces, and a fire pit. Experience the restful haven of rural Kentucky at its finest! Easy day trips to the Ark Encounter, KHP, Bourbon Trail, Keeneland, and UK Games!

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.

The Booth House

Welcome to our beautifully restored 4-bedroom home in the heart of Millersburg! Perfect for those in town for an event or a quiet getaway. Enjoy the charm of this historic home while still enjoying all the modern amenities you could need. Our location couldn't be better - right in the heart of everything Millersburg has to offer. Don't miss out on this unique and luxurious experience!

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.