Holiday rentals in Middleburg

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.

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.

*NEW* Secluded Cabin On Private Lake

Woodland Acres is located in the Heart of Kentucky, with spectacular views all around, year-round! Come enjoy this piece of heaven right on the Bourbon Trail! This unique and spacious hideaway has breathtaking views and is situated just 7 minutes from downtown Lebanon, KY. Enjoy a private lake and fishing dock, take a hike through the vegetation that surrounds you, or enjoy a cup of coffee on the wraparound porch. Ideal for leisure seekers, nature lovers, and families alike!

Ruckel's Rustic Retreat Cabin B

Our Cabin B sleeps 6 with a queen bed, four twin beds. The outdoor porch features a swing, chairs, and a cozy place to listen to the Frog Symphony, go Eagle Watching, and relax. Located a short walk away is Ruckel's Paylake, and Eubank park with walking trails, disc golf course, and playground. SMOKE FREE! Your stay includes a $20 meal voucher and two fishing passes so don't forget your fishing poles! Located across the parking lot from Ruckel's Restaurant.

2 Bedroom Home in Junction City

This home belongs to my parents. They travel frequently and are not always on the property. They have separate living quarters in the rear of the home that is separated from the rental space. There is no shared spaces in the home with them. Upon retirement, they decided to open up part of their home to assist in their quest to travel more. We hope that you enjoy the quiet neighborhood and the simple home they have lived in for many years.

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.

New custom built treehouse

Reconnect with nature at this unforgettable escape. Green River Breeze is a new custom built 4 season treehouse. This space allows you to immerse yourself in nature while enjoying all modern amenities of home. Suspended among the trees you will fall asleep in the loft on a king size bed. You will find a fully equipped kitchen, private bathroom and small living area BUT the real beauty is the expansive deck and outdoor firepit.

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

Haney’s Hideaway close to Green River Lake

Country cottage just minutes from Green River Lake boat ramp. Quiet peaceful setting to relax and unwind with lots of free parking. WiFi included and smart TVs in each bedroom and living room. Family friendly with large yard. Eat-in kitchen fully stocked with all the dishes and pots/pans you will need! Full-size washer and dryer onsite

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.

The Bunkhouse/Sleeps 15/7BR/5BA

Welcome to The Bunkhouse, a spacious 7-bedroom, 5-bath retret on 4 private acres in the rolling hills of Kentucky. With room for up to 15 guests, The Bunkhouse is ideal for family reunions, wedding groups, church retreats, hunting trips, lake vacations, business retreats, and weekend getaways.