Vacation rentals in Monticello

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Monticello

Guests agree: these stays are highly rated for location, cleanliness, and more.

%{current} / %{total}1 / 1
Top guest favorite
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
5 out of 5 average rating, 22 reviews

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!

Top guest favorite
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
5 out of 5 average rating, 16 reviews

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.

Top guest favorite
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
4.94 out of 5 average rating, 250 reviews

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.

Top guest favorite
Cottage in Monticello
4.98 out of 5 average rating, 60 reviews

Clean and cozy, only 150 yards away from water.

Serenity Cabin is nestled among the trees next to the Army Corp property which surrounds the lake. It has been described as clean and cozy. Only 150 yards from Old Fall Creek boat ramp. Even though no dock, it is a great place to launch a boat or to fish from shore. If a boat is needed, we are close to two marinas for rental. House has two upstairs bedrooms. One bedroom has a queen bed and twin bed, the other bedroom has a queen bed. The downstairs has a queen sofa bed in the living room.

Top guest favorite
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.
Cabin in Monticello
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!

Top guest favorite
Home in Monticello
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!

Top guest favorite
Cottage in Monticello
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.

Guest favorite
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.
Cabin in Monticello
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.

Top guest favorite
A small dining area is positioned in front of large windows, offering a view of the lake at sunset. A bottle and glass sit on the table, which is flanked by two benches. The warm hues of the setting sun fill the room.
Guest suite in Albany
4.97 out of 5 average rating, 275 reviews

Page's Legacy: Spring Getaway at the Lake

All rooms have a view of the lake and the deck overlooks Dale Hollow. We are a mile from Wolf River Boat Dock. The suite is downstairs with a private entrance. There are walking paths that encompasses 3 acres on the property. The private deck has a fire pit for chilly mornings to enjoy coffee or relaxing evening. There are some great day trips I have added to the "Host Guidebook" Click on "More about this location" and scroll to the bottom and click on "Show Host Guidebook"

Guest favorite
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.
Cabin in Monticello
4.91 out of 5 average rating, 113 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.

Guest favorite
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.
Home in Monticello
4.83 out of 5 average rating, 23 reviews

Relax at our country cottage near Lake Cumberland

Spend your days on Lake Cumberland and relax at our peaceful retreat in Monticello, KY. Nine generations of our family have enjoyed this property. Parts of the original cabin are incorporated into the current structure. Three outdoor seating areas, a fire pit, games and a wooded area let you enjoy the outdoors. The interior sleeps up to 8 and has everything you need! The home has been lovingly cared for and enjoyed by our family. We hope to share its gifts to you!

Top guest favorite
The cottage features a green metal roof and a welcoming front porch with multiple wooden rocking chairs. Two planters are positioned at either side of the entrance, and a outdoor grill is visible near the porch. A gravel path leads up to the door, with lush greenery in the background.
Home in Albany
4.94 out of 5 average rating, 136 reviews

Avery Acres

Country setting located 2 miles from Lake Cumberland with 3 boat ramps within an 8 mile drive. Fryman landing closest ramp to 76 Falls 2 miles,Marina @ Rowena 5.8 miles,Carter Dock Road 7.8 miles. Within 20 minute drive Grider Hill Marina and 1/2 hour drive to Dale Hollow Lake. Fire pit and outdoor gas grill supplied. We are on central time zone check in time is 4:00 PM and checkout is 11:00 AM We are pet friendly however there is a fee of $50 with a 2 pet limit.

Popular amenities for Monticello vacation rentals

Quick stats about vacation rentals in Monticello

  • Nightly prices starting at

    Monticello vacation rentals start at G$12,557 GYD per night before taxes and fees

  • Verified guest reviews

    Over 40 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Monticello rentals

  • 5 Average rating

    Monticello stays are highly rated by guests—averaging 5 out of 5!

  1. Airbnb
  2. United States
  3. Kentucky
  4. Wayne County
  5. Monticello