Holiday rentals 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.

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!

Hidden Creek Schoolhouse

Not all escapes are found on maps; some are found in time. Tucked into a quiet hollow between Dale Hollow Lake and Lake Cumberland sits a 1919 schoolhouse where stories linger and life slows. Original wood floors whisper history, the seasonal creek hums when it pleases, and the skies put on a show in every season. Wander to the lakes or stay wrapped in the stillness…spring blooms, autumn glows, winter hushes. Hidden Creek is a storybook stay you step into, not rush through. Book early!

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!

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.

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.

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 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.

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 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

Lake House "Dar Bida" Monticello

Forget your worries in this spacious, nearly 4,000 sq ft, and serene space. You will enjoy the silence and magnificent view on Lake Cumberland. "Dar Bida" is the ultimate place to relax and enjoy time with your family or friends. Lake Cumberland offers plenty of possibilities for outdoor activities such as paddling, boating and fishing. Two boat ramps are within 5 miles and boats can be stored at a dedicated boat storage area within the gated residence.

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.