Holiday rentals in Monticello

5 out of 5 average rating, 22 reviews

The entrance features a white door adorned with a festive wreath, set against a bright red exterior wall. A decorative mat lies at the foot of the door, and a light fixture is positioned above, providing illumination during evening hours.

Barn in Monticello

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!

5 out of 5 average rating, 16 reviews

A well-maintained cabin is set amidst a lush green landscape, featuring a sloped metal roof and a spacious front porch with steps leading to the entrance. A gravel driveway curves in front of the home, providing access to the property surrounded by trees.

Home in Albany

Hooked on the Lake - 6 miles from Marina Rowena

Your perfect getaway adventure awaits! Just 6 miles from Marina@Rowena, our cozy retreat is ideally located near a beautiful lake for boating, fishing and relaxing on the water. After a day of adventure, unwind in a comfortable space with a fully equipped kitchen. With ample parking for your trailer and easy access to nature, our home is the perfect base for your next outdoor escape. Please note: The lake is a short drive, not within walking distance as listed by Airbnb’s default map features.

4.97 out of 5 average rating, 158 reviews

An outdoor seating area is arranged around a fire pit, with chairs positioned for comfort. The night sky glows softly from the moonlight, casting a gentle light on the surroundings. Trees are faintly visible in the background, enhancing the serene atmosphere.

Home in Bronston

Peaceful Getaway near Conley Bottom & Burnside

Welcome to our countryside getaway nestled on almost 5 acres within 5-20 miles of Burnside, Lee's Ford, and Conley Bottom Marinas. Enjoy the day on Lake Cumberland. Come back to relax, eat, drink & be merry. Gather around the outside barbecue area and fire pit or snuggle up inside next to the fireplace, playing games or watching a movie. Whether you are on a couple's retreat, fishing buddy's getaway, or family vacation - the house and outdoor area provide plenty of room to relax and enjoy.

4.94 out of 5 average rating, 252 reviews

A covered deck area features comfortable seating and overlooks a lush landscape with a serene lake in the distance. Sunlight filters through the trees, illuminating the wooden flooring and creating a peaceful retreat for relaxation.

Tiny home in Monticello

Tiny LakeView Cottage~Pets! 1 nights available

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.

The cabin exterior is enveloped by lush greenery, featuring a welcoming wooden deck with a railing adorned with potted plants. Large glass doors invite natural light, complemented by multiple windows that enhance the warm, woodsy atmosphere of the structure.

5 out of 5 average rating, 24 reviews

Cottagey-Cabin, Private~Firepit! July Books Fast!

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 of CONLEY BOTTOM MARINA from its secluded, private, 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!

4.99 out of 5 average rating, 106 reviews

Lake Cumberland ~ SPA~ Fire Pit~ KING Ensuites

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!

5 out of 5 average rating, 107 reviews

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.

A wooden sign hangs from a post displaying 'Lakeside Lodge' against a backdrop of a rustic cabin and lush greenery. The cabin showcases a stone chimney and a steep roof, surrounded by trees, with a gravel driveway leading up to the entrance.

4.97 out of 5 average rating, 31 reviews

Lakeside Lodge Cabin

Experience the ultimate Lake Cumberland getaway at Lakeside Lodge. Nestled in Kentucky's natural beauty, this cozy cabin is perfect for families or small groups. Enjoy mornings surrounded by nature and evenings by a warm fire. A quick 5-10 minute walk leads you to a private neighborhood beach and boat ramp, making lake access effortless. Whether you’re hiking forest trails or exploring the water, Lakeside Lodge offers the perfect blend of comfort and adventure. Book your stay today.

The cabin entrance is framed by a wooden ramp leading to a covered porch. A picnic table is positioned on the grassy area beside the porch, providing an outdoor seating option. A privacy fence surrounds the yard, creating a secluded space.

4.96 out of 5 average rating, 25 reviews

D&D Cabin at Lake Cumberland *Pets Welcome*

Our cabin is a cozy place to relax and enjoy with the whole family. It is centrally located in Monticello, Ky. There is 2 parking areas to accommodate guest and boat parking. We are 5 minutes from Walmart and Black Stallion Steakhouse. Conley Bottom and Beaver Creek Resort is within 15 minutes. Nearby are multiple docks for fishing. We have an outdoor grill and picnic table with privacy fence. Marina Rowena is 28 minutes away. As well as Safe Harbor Marina is 25 minutes from here.

The exterior of a charming cabin is visible among a lush, wooded setting. The cabin features a metal roof and wooden sides, with a porch that invites relaxation. A blossoming tree adds a splash of color to the serene landscape, surrounded by green foliage.

4.91 out of 5 average rating, 114 reviews

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.

A recently renovated cottage is surrounded by large, shady trees, featuring a spacious deck with stairs leading up to the entrance. A hot tub is positioned nearby, with a grill covered by a protective cover, set against a backdrop of lush greenery.

4.97 out of 5 average rating, 75 reviews

'Top of the Hill'- Cozy Retreat with Hot Tub!

Take a break and unwind at this peaceful cottage nestled under large shady trees. 😊 Located only five miles from Conley Bottom Marina. 😊 Within one mile of two public boat ramps for launching your boat, fishing, or swimming. Featuring: 💥 Hot tub (sized for 2, max 4 person) 🛏️ Two bedrooms, queen beds 🛋️ Sleeper sofa (full size) 🍽️ Fully equipped kitchen 🧺 Laundry machines 🔥 Fire pit ♨️ Gas grill 🌳 Deck 🚤 Parking for smaller boat/trailer

The cabin's rustic exterior features a wooden façade with green accents and a covered porch. Two chairs are positioned beside a small table, inviting outdoor relaxation. Surrounding trees provide shade, while landscaped gravel and flowers enhance the natural setting.

5 out of 5 average rating, 22 reviews

Luke’s Porch

Relax at this unique custom crafted getaway cabin. Luke’s Porch is nestled in the woods on one of the highest ridges in the area. Various trails are right outside the door for hiking. The Orchard boat ramp is just 1 mile away and Beaver Creek Marina is only 3 miles. Beaver Creek is a great area of Lake Cumberland for kayaking with multiple waterfalls and excellent fishing. We have ample boat parking and are Pet friendly with an additional cleaning fee.

Popular amenities for Monticello holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Monticello

A single-story home is situated on a spacious grassy area, surrounded by trees. The building features a light-colored exterior with a dark roof and a welcoming front porch. Gravel leads up to the entrance, providing easy access to the property.

5 out of 5 average rating, 37 reviews

Hadlee's Hideaway

A light blue single-story house surrounded by lush greenery is shown. A well-maintained lawn leads to the front, where porch seating and a front door are visible. A vehicle is parked in the driveway, with trees providing natural shade.

5 out of 5 average rating, 4 reviews

Wake N Lake

A single-story cottage is surrounded by greenery, featuring a gravel driveway leading to a covered entryway. The structure has a light-colored exterior and large windows, allowing for ample natural light. A few outdoor chairs are positioned near the entrance for relaxation.

4.84 out of 5 average rating, 31 reviews

Cozy 3-Bedroom Beaver Creek Cottage

5 out of 5 average rating, 8 reviews

4J’s Getaway|3BR Home|Near Marina|Boat Parking

A spacious living room is highlighted by a large 65-inch TV on a wooden entertainment unit. A dark sectional sofa is arranged around a patterned area rug with a plant in a gold pot nearby. Natural light enters through a window, creating a bright environment.

4.89 out of 5 average rating, 27 reviews

Home 0.2 miles from boat ramp with game room

A cozy cottage is surrounded by a gravel yard, with a firepit situated in the foreground. The exterior features blue siding and a welcoming front door, while a grassy area and trees provide a natural backdrop. A grill is visible to the side, enhancing outdoor dining options.

4.93 out of 5 average rating, 120 reviews

The Cozy Lake Cottage

The entrance of the lake house features a charming front porch with two black chairs, inviting relaxation. A white door is flanked by two windows with decorative shutters. The light pink exterior is complemented by greenery from nearby trees, creating a welcoming first impression.

5 out of 5 average rating, 21 reviews

Lake Cumberland Beaver Creek Marina

The exterior of the home is showcased at twilight, featuring a welcoming porch with seating. Soft light emanates from within, illuminating the front door and surrounding windows, while lanterns provide additional ambient lighting. A well-maintained yard is visible in the foreground.