Holiday rentals in Middleburg

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.

Lake front Cabin - Private dock

This cozy a-frame is located in the lakeside neighborhood of Echo Point, on Cumberland’s South Fork. Swim or fish off the dock, bring a paddle board, or drop a boat in at the nearby ramp. Relax on the deck with rock wall views and towering trees. Perfect for a couple or a small family get away. Walk to water/dock via a rustic path and stairs (it’s a steep climb!) *Not ideal for people with mobility constraints.* Stores & restaurants are 15 min drive. Dogs (2 max) welcome for add'l fee.

The Lodge at Marble Creek

Escape to The Lodge at Marble Creek, a modern cabin tucked in the woods overlooking beautiful Marble Creek and its palisades. This 3-bedroom, 2-bath getaway sleeps 6 guests. Relax in the hot tub, unwind in the sauna, or enjoy a soak in the spa-style tub. Gather by the indoor or outdoor gas fireplaces, or end the night around the firepit under the stars. Just minutes from Nicholasville and Lexington, yet it feels like you’re deep in the Gorge — peaceful, private, and surrounded by nature.

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.

The Bunkhouse

The whole group will enjoy easy access to everything from this centrally located property. It’s 8 miles from Highway 27, and 8 miles from Liberty & Tarter Industries on 127. This 4 acre property is perfect for multiple family get-togethers, Business Meetings, and Parties. Inquire about the fees for those uses. Meals can be provided at extra cost. See Menu. Lake Cumberland & Herrington Lake are about 30 minutes away and Lake Liberty is approximately 9 miles away.

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.

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

8-Acre Escape: Fishing Pond, Waterfalls, Disc Golf

Escape to our peaceful Kentucky lake house on an 8-acre private retreat on Lake Cumberland. Perfect for families and nature lovers, this pet-friendly home offers stunning views, a private pond, waterfalls, and a cozy fireplace. Enjoy modern amenities like Starlink internet and a fully equipped kitchen. A year-round destination for relaxation and adventure.

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.

Hometown Country Getaway

Welcome to your home away from home in the heart of Liberty Kentucky! A peaceful place to stay and relax with your whole family. Enjoy a brand new house with a fully equipped kitchen , 3 bedrooms ,2 full bathrooms, free WiFi and a smart TV .