Holiday houses in Monticello

Bluegrass Gables: Lake Cumberland Cottage

Relax in the forest is this amazing 4bd/2.5ba cottage. Only minutes to the Ramsey Point boat ramp, this is your base for your Lake Cumberland vacation. Bring your boat; ample parking onsite. Don't have a boat? No problem, Beaver Creek and Conley Bottom marinas are close by. House features modern amenities and a fully stocked kitchen. Enjoy the fireplace indoors or the firepits outdoors. Forest views and fresh air galore await you, especially from the hot tub! Absolutely no smoking inside or out.

Family · Value · Cleanliness

The Cozy Lake Cottage

This cozy cottage is tucked away in a peaceful wooded area, giving you the privacy you crave while being just minutes from beautiful Lake Cumberland. You're only about five minutes from Conley Bottom, and there are two other docks just a short drive away. Take nature walks and you might spot deer and other friendly wildlife. In the evenings, enjoy sitting around the campfire! The driveway is long enough for your boat and vehicle. Enjoy a perfect mix of comfort and nature in this lovely getaway!

Value · Location · Indoor spaces

The Big Red Barn at LCK

Enjoy the lake or some quiet nature time in this secluded Barndominium on approx. 3 acres in the woods. Near Conley Bottom with plenty of room to park your boat trailer. Enjoy nearby public access to the lake, 5 minute drive to Conley Bottom Resort, or nearby Daniel Boone National Forest, Cumberland Falls, or some Pool Hall burgers in Downtown Monticello, Kentucky. Property is brand new and offers large rooms, well appointed kitchen, and walk in showers. Great covered porches and fire pit!

Family · Location · Nearby

Hidden Creek Schoolhouse

The Hidden Creek Schoolhouse is more than a stay; it's a chance to slow down. Lovingly restored from a 1919 schoolhouse, this one-of-a-kind retreat rests in a quiet hollow where time seems to move a little differently. Original wood floors, a seasonal creek, and evenings lit by fireflies create a setting made for long conversations, morning coffee, and doing wonderfully little. Thoughtfully renovated and rich with character, it offers the rare luxury of stillness in a world that rarely pauses.

Location · Family · View

Lake House "Dar Bida" Monticello

Escape to Dar Bida, a secluded 4,000 sq ft retreat overlooking beautiful Lake Cumberland. Enjoy breathtaking lake views, peaceful surroundings, spacious living areas, and a well-equipped home designed for comfort. Whether you’re boating, fishing, kayaking, hiking, gathering with family and friends, or simply unwinding on the deck, Dar Bida is the perfect getaway. Two boat ramps are within 5 miles, with boat storage available in the gated community. Marinas are also just a short drive away.

Location · Value · Sleep quality

Lake Cumberland Cottagey Cabin, Secluded/Firepit!

Serenity, tranquility & an inner peace is what you'll feel upon entering! Our 3-level, 4BR, 2BA cottagey Cabin accommodates 8 guests and boasts a seasonal view in Fall/Winter of CONLEY BOTTOM MARINA from its secluded, wooded lot! Inside, the warmth of natural woods will envelop you! The chef in your group will love the adorable kitchen equipped with every imaginable gadget, spice & cooking basic! Appointed in Cottagecore design, SERENITY RIDGE is the perfect blend between yesterday and today!

Location · Value · Nearby

Tiny LakeView Cottage~Pets~Best Sunset~Kayaks!

We welcome your fur babies!! Kayaks available! Ice maker! Coffee pot w/coffee & creamer! Adorable, cozy tiny house with two decks & bonfire pit overlooking Lake Cumberland! It is located in Monticello, Ky, in a rural part of the area. It’s about 12 minutes to town. There is very close (driving distance) swimming access, kayaking, boating, boat ramps, fishing & marinas. On a dead end street, so very peaceful. Kayak rental is available for $25. per day/per kayak. Pet fee $50/$75 per stay.

Value · Location · Comfort

Cozy Comfort. Only 175 yards from the water.

Cabin House is located at beautiful Lake Cumberland near Monticello, KY. It is located approximately 175 yards from Old Fall Creek boat ramp. This is a Free boat ramp. No dock. If you should need to rent a boat, we are located close to the resorts at Conley Bottom and Beaver Creek. The cabin is known for being clean and comfortable. It is nestled among the trees next to land overseen by the Army Corp of Engineers. The area is always beautiful no matter what season. Come and Enjoy!!

Family · Location · Air conditioning

Beautiful Farmhouse near Lake Cumberland

This beautiful farmhouse has lots of amenities, 3 bedrooms, 2 bath. Coffee bar, Nice backyard with fire pit, Weber gas grill, 6 camping chairs to sit by the cozy fire and corn hole and basketball goal for added fun! Full front porch and nice quiet back porch. Laundry soaps, shampoo, propane, laundry detergent etc included. 4 flat screen TV’s. Activities for kids. Swing set, Located 5 minutes to Beaver Creek Marina , 15 minutes to Conley Bottom and less that 5 minutes to city limits.

Value · Location · Barbecue

HOT TUB~ Fire Pit~ KING Ensuites~ Lake Access

Escape to Barndo Bliss, a newly built 4bd/3.5ba retreat nestled in Lake Cumberland's serene forests, just 1.2 miles from Ramsey’s Point boat ramp! Perfect for families and friends, this home features TWO luxurious King En-suites. No boat? No problem! Nearby Beaver Creek Marina offers rentals. Enjoy evenings by the large firepit surrounded by nature, perfect for s'mores, and unwind in the luxurious spa. Experience the tranquility of Lake Cumberland—book your stay at Barndo Bliss today!

Location · Family · Layout

The Cozy Cabell Cottage

It’s time for an adventure at our vacation rental, Cabell Cottage. With Lake Cumberland only 5 minutes away via the Cabell landing....really your boat is 5 minutes from being in the water; the cottage can be your base for all things fun on the lake (swimming, boating, and fishing). Did I CATCH your interest with fishing. However, if it’s a retreat you seek, the cottage is also for you as it sits in a quiet, very pretty, rural area of Wayne County, Kentucky, where 5 can sleep easily.

Location · Value · TV

The Oak. Cabin w view close to Conley Bottom.

Escape to this newly built cabin just minutes from Conley Bottom and Lake Cumberland. Perfect for families, couples, and lake lovers, this cozy retreat sleeps 6 with a queen bedroom, loft twins, and a sofa bed. Spend your days boating, fishing, hiking, or exploring the area, then unwind by the fire under the stars. Whether you’re here for adventure or relaxation, you’ll feel right at home at Buffalo Trace Retreat.

Condition · Cleanliness · Parking