Vacation rentals in Monticello

Bluegrass Gables: Lake Cumberland Cottage

Relax in the forest is this amazing 4bd/2.5ba cottage. Only minutes to the Ramsey Point boat ramp, this is your base for your Lake Cumberland vacation. Bring your boat; ample parking onsite. Don't have a boat? No problem, Beaver Creek and Conley Bottom marinas are close by. House features modern amenities and a fully stocked kitchen. Enjoy the fireplace indoors or the firepit outdoors. Forest views and fresh air galore await you, especially from the hot tub! Absolutely no smoking inside or out.

Garage Door to the Wilderness!

Welcome to this stylish and sleek tiny home that's perfect for modern living! With ample space to sleep 4, features a bathroom complete with a beautifully tiled custom shower. The kitchen is a chef’s delight, black cabinetry and elegant granite counters.Enjoy the seamless flow of heated tile flooring throughout, leading you to the covered back porch where you can sip your morning coffee! The back garage door offers easy access to nature’s beauty. Located 5 minutes from either town or the lake!

Countryside stay near Cumberland Falls-SF 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.

Lazy Days Wilderness Cabin

Nature abounds, If hiking, horseback riding, four wheeling or just relaxing is what you crave, then this is the place for you! The property is 24 acres, sitting on the edge of Big South Fork National Park. The front yard is big enough for games. When you are through for the day and after enjoying the enclosed hot tub/pool inside, go outside and enjoy the fire pit area. Horses welcome, small pasture area, no barn. Owners live on property, always available. Pet fee $25. Welcome to our cabin.

Ranger's Retreat cabin at Big South Fork

The Ranger's Retreat (RR) cabin by Big South Fork will give you all the privacy you want and still convenient to town for the essentials. All of this plus with one of the Southeasts' premier National Park area's in your backyard. The RR cabin is a genuine log cabin made of real white pine logs. It features 1 bedroom, 1 bathroom, kitchen, living room and a loft. The RR cabin is great for couples, but the loft with 2 twin beds provides room for a total of 4. Dog friendly (sorry no cats).

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!

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.

Dixie Mtn. Hideout

Enjoy a breath taking Mountain view from your private log cabin as you drink your morning coffee. With memory foam beds you will wake refreshed and ready to enjoy all the Lake Cumberland area has to offer. Within 5 miles to General Burnside Sate Park and boat ramp and Burnside Marina. Your vacation home is only 10 miles from downtown Somerset, somernites car cruise capital! Boat parking available with turn around. Dixie Mtn. Hideout, when you're away from home, we welcome you home!

Page's Legacy: Winter Hideaway 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"

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.

The Bear’s Den

Take a break and unwind in the beautiful Smokey Mountains in southern Kentucky. We are situated less than 5 miles from the famous Cumberland Falls! We are close to many hiking trails and water sports. This one bedroom, one bathroom cabin boasts a full kitchen and a washer and dryer. The deck provides a peaceful view of the beautiful forest as well as a great place to relax and grill your favorite meal! An air mattress is provided for additional guests.