Vacation rentals in Monticello

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!

The Little Hideaway at Beaver Creek

Cute tiny cabin located only 1 mile from marina Plenty of parking Max guest: 5 NO pets allowed. $500 charge if suspected -King size bed -Twin sleeper sofa -Fully equipped kitchen -Spacious bath (stand up shower, toilet & sink) -Washer and dryer -Local cable -Free Wifi -Covered porch -Fire pit (wood & starter fluid supplied) -Charcoal grill -Linen & towels/washcloths provided Policy: NO smoking NO pets NO parties/events of any type 2 night min. stay Must be 23 yrs. or older to reserve

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.

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.

Lake Cumberland Cottagey-Cabin 15% OFF AUG 2+NTS!

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!

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.

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!!

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!

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.

The Stable @ Bluegrass Gables

Enjoy some retro vibes in this converted barn. Indulge your senses, from the smell of the pine shiplap to the sounds of the wind chimes on the breezy covered porch or some vintage vinyl on the victrola turntable. Light a fire and watch the flames dance in the wood burning stove. Enjoy sips of your favorite beverage from a rocking chair with a view of the Appalachian foothills. Soak in the hot tub! Vintage china, glassware, art, vinyl, furniture, games, it's all in the details.

Hot Tub & Seasonal Lake Cumberland Views

Welcome to Your Lake Cumberland Getaway! Tucked away in the peaceful hills of Monticello, KY, this cozy 2-bedroom, 1-bath retreat offers the perfect mix of comfort, privacy, and seasonal lake views. Whether you’re here to unwind or explore Lake Cumberland, this home is designed for relaxation year-round. Same great property under new ownership! Previous average rating of 4.95 with 80+ total reviews! Most recent 5 star reviews hosted by myself.

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.