Holiday rentals in Middleburg

Bourbon Trail + Hot Tub +Walk to Dine + Fire Pit

Hot tub, Fire pit , Bourbon Trail Location, 10 Miles from Maker’s Mark and many more distilleries. Boutique style. Customized Complimentary Itinerary , Walkable restaurants, Fenced dog yard. The Kentucky Barrel House a unique retreat on the Bourbon Trail. Equipped kitchen, walk to downtown restaurants. Minutes to: Maker’s Mark, Willett, Bardstown Bourbon, Heaven Hill, Beam and many more. Near Cornerstone Acres Events, The Grove At Silverton Hill, My Old KY Home. Fast WIFI, Fireplace (electric)

Quaint cottage in the heart of Danville

Cute renovated cottage in the heart of historic Danville. Walking distance to downtown and all of Centre College. Enjoy local restaurants, the Saturday morning Farmers Market, and the amazing shops on Main Street. The Cottage is fully furnished and beautifully decorated to make your stay comfortable and relaxing. All beds are memory foam mattresses, and all linens are 100% cotton with hypoallergenic fiber filled pillows and comforters. The front porch & deck offer outdoor space to sit a while!

Country Charm

This house is on a peaceful country road and has three bedrooms, two full baths, and a double driveway for parking. The newer appliances include a refrigerator, cook stove, dishwasher, and coffee makers. For your convenience, we provide the coffee for you to prepare. You will find water and soda in the refrigerator. Nearby are the Cedar Creek Lake, Lincoln County Fairground, and the Boyle County Airport. It's very near Stanford, Kentucky, about ten miles from Danville, and ten from Lancaster.

The ranch house. Relax and unwind

Quiet, peaceful, country setting. There are country roads for walking and bike riding. For the boaters and fishermen, we are just minutes away from Arnold’s landing boat ramp and also Holmes Bend marina on beautiful Green River lake. For the hunting enthusiast, there are 20,000 plus acres of public land available for spring and fall hunting, with an abundance of turkey and deer. Close to Campbellsville University and Lindsey Wilson in Columbia. Lake Cumberland is also a short drive away.

Farmhouse Escape at Smith Acres in Central KY

This beautifully renovated farmhouse offers a peaceful, romantic escape in the heart of Kentucky farm country. Tucked away on 65 acres at Smith Acres, it’s where rustic charm meets modern elegance. Whether you’re planning a family getaway, a weekend for two, or booking as part of a wedding celebration, you’ll find cozy spaces, sweeping views, and that sweet stillness that invites you to slow down and savor the moment. Perfect for reconnecting and making lasting memories together.

Elegant Modern Rustic Retreat w/ Hot Tub

A steel framed industrial warehouse converted into an upscale two bedroom rustic-chic living space located within 8 miles of beautiful Lake Cumberland and within 5 minutes of Downtown, Somerset. The city is yours to explore from your own private 2 bed, 1 bath modern rustic retreat. Picture comfy beds, full bathroom, a kitchen built for entertaining, all under a metal tin roof for those rainy days when you just want to curl up and relax.

Blue Moon Cottage w/ Pergola & Scenic Views

Escape to Blue Moon Cottage, a peaceful retreat in Kentucky's Knob lands just 5 miles from downtown. Surrounded by nature, this cozy getaway offers beautiful views, quiet mornings, and relaxing evenings by the fire or in the pergola. This home offers: 🌄 Scenic deck & pergola with views 🔥 Cozy fireplace 🛏️ 2 queen beds + 2 twins 🍽️ Full kitchen w/ electric range 📶 Free WiFi Perfect for families, couples, or a relaxing getaway.

Ruckel's Rustic Retreat Cabin A SMOKE FREE

Ruckel's Rustic Retreat SMOKE FREE CABINS 192 W Highway 70, Eubank, KY 42567-7536, United States Located in beautiful Pulaski County 192 W Hwy 70 Eubank KY Lodging includes..... 2 fishing passes A $20 meal voucher Free admission to the Frog Symphony Unlimited Eagle Watching Serious relaxation on the porch swing. VIP status for the Goose Don't forget your fishing poles! Playground- Park within walking distance.

Coffee with the Squirrels

New chalet only 5 minutes to city of Somerset and 5 minutes to Lake Cumberland! Cozy 1 king size bedroom with custom features throughout. Walk out on your master suite deck and have coffee with nature! Full size bathroom w custom tile. Back deck that overlooks woods and wildlife. Sometimes there is a neighbor who has a dog that barks a couple housss down, I’m sorry if it does, doesn’t happen often

TT’s Treehouse

Cozy studio guesthouse with beautiful oak vaulted ceiling overlooking scenic woods and creek just 10-15 minutes from boat ramp on Lake Cumberland. Covered porch around guesthouse with gas grill access. Kitchen fully stocked. Full size sofa couch, and 2 full size floor mattresses in loft. Free wifi available. Onsite boat parking available. Fire pit and fire table available-both outside. No smoking.

Horse & Buggy Country Inn

Nestled on 3 acres in BEAUTIFUL Amish & Mennonite country...this ADORABLE chalet is the PERFECT getaway! Only minutes away from the local Amish & Mennonite stores! Only 6 miles from the Famous Bread of Life Cafe! Within 1 mile from The Galilean Children’s Home! Just minutes away from beautiful lake Cumberland and green river lake

Home in Liberty

Enjoy easy access to everything from this 2 bedroom 1 bath home centrally located in the middle of Liberty. This non-smoking house has central heat/air. 1 mile to Ag Expo center, 5 miles to bread of life, 27 miles to lake Cumberland, 30 mins to Danville and only 1/4 mile for liberty’s Apple festival and court house.