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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.

Lake front Cabin - Private dock

This cozy a-frame is located in the lakeside neighborhood of Echo Point, on Cumberland’s South Fork. Swim or fish off the dock, bring a paddle board, or drop a boat in at the nearby ramp. Relax on the deck with rock wall views and towering trees. Perfect for a couple or a small family get away. Walk to water/dock via a rustic path and stairs (it’s a steep climb!) *Not ideal for people with mobility constraints.* Stores & restaurants are 15 min drive. Dogs (2 max) welcome for add'l fee.

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.

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!

Elisi's Cozy Nook 3.2 mile from Marina Rowena.

Relax and enjoy a cozy quiet farmhouse large yard spacious circle drive.Sleeps 5 1 full bed, full sofa sleeper, twin sleeper, & paknplay. crib. The peaceful atmosphere will take you back to the days of back porch swings surrounded by the sound of the birds and cattle grazing in the fields. The perfect place to relax and unwind after a day on the lake or an adventure at one of the many places of interest within the area. Located just 3.5 miles from Marina Rowena on Lake Cumberland.

Whispering Woods Cottage | Hot Tub | Pool

Welcome to Whispering Woods, your peaceful sanctuary nestled near Lake Cumberland. Step into our cozy 1-bedroom cottage that offers tranquil surroundings and a restorative night's sleep after your day's adventures. Perfect for a romantic getaway, a solo retreat, or a change of scenery for remote workers, Whispering Woods provides space for up to two guests. ☆ Book your escape at Whispering Woods today to experience the enchantment of lakeside living. Your perfect retreat awaits! ☆

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!

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.

Lake Life Dot Calm (Slip Available)

Welcome to your new peaceful retreat less than 2 miles from Jamestown Marina and Lilly Creek boat ramp. SLIP RENTAL available. ROOM TO PARK your boat and trailer in the driveway! Take a walk down the street (or ride one of our bikes) to see gorgeous lake views! This 3 bedroom, 3 bathroom house has what you need for your stay! Each bedroom has its own full bathroom. Remodeled kitchen, game room in the garage, smart TVs, great back deck, and much more!

Lake Escapes on the Square

The whole group will be comfortable in this spacious and unique space located right on the square in Jamestown. Bedroom 1 - Queen Bed Bedroom 2 - Full Bed Located 3.5 miles from Jamestown Marina, 12 miles to Wolf Creek Dam, 13 miles to State Dock, 0.8 miles to Dollar General Market, walking distance to Reel Java, Giovanni’s Pizza & Snap’s Soda Shop! 2 parking space maximum NO ROOM FOR BOATS OR TRAILERS This apartment is located upstairs!

Lake Cumberland State Park Villa

Fish, hike, swim in the heated pool, play putt putt golf, enjoy archery courses, horseback riding, play basketball, tennis or pickleball all while nestled in the Apple Valley Resort! Your 2 Bedroom, 2 Bath Townhome awaits! There is also a Gazebo with several picnic tables, grills, a playground, a boat shed and more!!! We look forward to hosting you, your friends & family!! Pool is closed for season.