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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!

Peaceful Getaway near Conley Bottom & Burnside

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.

Lakefront Views at Wolf Creek Marina! HotTub+Pets

Pet Friendly, hot tub & 1.5 mi to Wolf Creek Marina! Our beautiful Lakefront 3 bedroom (one a sleeping loft), 2 bath cabin is perched above the main lake of Lake Cumberland. The 2 story, partially covered decks provide incredible & relaxing water views all year round. Bring your boat; ample parking onsite. Don't have a boat? No problem, boat rentals are close by! Sleeps 10 comfortably. We will provide everything we can think of to make your stay in our home a wonderful and memorable one.

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!

Jamestown - KY Lake Cottage | Boat Parking

Welcome to your seasonal getaway at Harbor Springs Cottage near beautiful Lake Cumberland! Inside, our three private bedrooms offer a haven of comfort for you and your guests, ensuring a restful night's sleep after a day of lake time. Whether you're seeking a romantic retreat, a family getaway, or a solo escape, Harbor Springs Cottage has got you covered. ☆Book your stay at Harbor Springs Cottage today and discover why life truly is better by the lake. 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.

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 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 Luxury! Lake views, golf, hot tub

Come enjoy the best that Lake Cumberland has to offer. This beautiful, spacious, and private home offers one of the best views of Lake Cumberland you will see. With 4 bedrooms (7 beds) and 4 bathrooms you will have plenty of space to sleep up to 13 guests—making it a perfect trip for families and friends. There is a hot tub, pool table, a GOLF pad, cornhole and tons of games (Spike Ball, Can Jam and more) to take your stay to the next level.

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.

8-Acre Escape: Fishing Pond, Waterfalls, Disc Golf

Escape to our peaceful Kentucky lake house on an 8-acre private retreat on Lake Cumberland. Perfect for families and nature lovers, this pet-friendly home offers stunning views, a private pond, waterfalls, and a cozy fireplace. Enjoy modern amenities like Starlink internet and a fully equipped kitchen. A year-round destination for relaxation and adventure.