Holiday houses in Monticello

Country stay near the Falls-Polar Express Railway

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.

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.

Tandy Tiny House

Welcome to Tandy Tinyhouse! This Adorable 1Br is Brand New and has everything you need! Very Modern Kitchen w/tiled backsplash, Microwave, Keurig, Refrigerator, Range and Granite Counters. LTV Flooring and 10ft Ceilings throughout. En-suite features a Barn door and Tiled Shower. Washer/Dryer Combo just off of the Kitchen Area. Amazing location 3 minutes to Downtown Somerset and 10 minutes to Lees Ford Marina. You will want to stay here again and again! Please leave mini split 68 or above

Cozy Countryside Cottage at Lake Cumberland

Celebrate autumn, all it's beauty, and enjoy days of tranquility at our family home 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!

Cozy Cabin - Lake Cumberland w/ Hot Tub

Our cozy cabin is located on Lake Cumberland in Monticello close to Somerset and two great marinas, Conley Bottom being our favorite! We have partial lake views in the fall, winter and spring and a hot tub on the deck to enjoy the views, along with the fire pit below. We have 2 bedrooms, one bathroom and a pull out couch. The large wrap around deck is perfect for playing games and hanging out. Please note there is no lake access from the property. Also - Please note stairs to access.

Hot Tub, Fire Pit, King En-suites, Holiday Ready,

Escape to Barndo Bliss, a newly built 4bd/3.5ba retreat nestled in Lake Cumberland's serene forests, just 0.8 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.

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

Take a break and unwind at this peaceful cottage nestled under large shady trees. Located within one mile of two public boat ramps for launching your boat, fishing, or swimming. Five miles from Conley Bottom. The house features a hot tub with room for up to four people. There is room to park one or more smaller boats (23 ft or less). Two bedrooms, one full-size sleeper sofa, one bathroom with walk-in shower, a large shady deck, outdoor wood-burning fire pit, and gas grill.

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.

Page's Legacy: Favorite Fall Getaway

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"

Hidden Creek Schoolhouse

Located between Dale Hollow Lake and Lake Cumberland, tucked in a Hollow down a quiet track, you’ll find a schoolhouse from way back. Built in 1919, cozy and sweet, with original wooden floors and charm complete. The creek hums low when the time is right, and summer skies glow soft and bright. Lakes are near if you choose to roam, but the Hollow feels like home. Spring blooms, autumn glows, winter hushes with snow; at Hidden Creek, time slows in a storybook place.

John L. Wright Cabin

Enjoy a peaceful escape. This newly built cabin with all the modern features is located in historic Stearns, KY. Surrounded by trees and overlooking a beautiful pasture, visitors can relax and enjoy the Big South Fork and Daniel Boone National Forest hiking and horseback riding trails, kayaking, and Cumberland Falls scenic attractions. Also enjoy and view the Big South Fork scenic railway train. Security cameras are turned off when guest are occupying cabin.