Holiday rentals in Wayne County

The Lake Nest Off Jamestown Square - Hot Tub!

Enjoy the HOT TUB at The Lake Nest! - Walking distance of town square to restaurants via sidewalk close by - Approx. 4 miles to Jamestown Marina - 3 miles to Lily Creek Boat Ramp Beautiful neighborhood in town & close to lake - 2 bedroom with 3 beds (1 King, 1 Queen & 1 Queen Sleeper Sofa) - 1 full bath - Fully equipped kitchen - Hot tub - Plenty of parking & more! No parties, no smoking, no pets, etc. Note: 1 security camera on the front porch for security purposes only. No other cameras.

Lake Cumberland | New | Secluded | Cozy | Sleeps 5

Escape to this cozy Lake Cumberland retreat with stunning sunset views—perfect for relaxing and enjoying the outdoors. Just minutes from the lake, this peaceful getaway is ideal for couples, families, or small groups looking for a quiet, comfortable stay. Plenty of parking for trucks and boats! Unwind on the porch as the sun sets or fire up the grill after a day on Lake Cumberland. Inside, you’ll find a clean, modern space designed for comfort with everything you need for an stress-free stay.

Hidden Creek Schoolhouse

The Hidden Creek Schoolhouse is more than a stay; it's a chance to slow down. Lovingly restored from a 1919 schoolhouse, this one-of-a-kind retreat rests in a quiet hollow where time seems to move a little differently. Original wood floors, a seasonal creek, and evenings lit by fireflies create a setting made for long conversations, morning coffee, and doing wonderfully little. Thoughtfully renovated and rich with character, it offers the rare luxury of stillness in a world that rarely pauses.

Lake House "Dar Bida" Monticello

Escape to Dar Bida, a secluded 4,000 sq ft retreat overlooking beautiful Lake Cumberland. Enjoy breathtaking lake views, peaceful surroundings, spacious living areas, and a well-equipped home designed for comfort. Whether you’re boating, fishing, kayaking, hiking, gathering with family and friends, or simply unwinding on the deck, Dar Bida is the perfect getaway. Two boat ramps are within 5 miles, with boat storage available in the gated community. Marinas are also just a short drive away.

Lake Cumberland Cottagey-Cabin 15% OFF AUG 2+NTS!

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 in Fall/Winter of CONLEY BOTTOM MARINA from its secluded, 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!

Tiny LakeView Cottage~Pets~Best Sunset~Kayaks!

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.

Cozy Comfort. Only 175 yards from the water.

Cabin House is located at beautiful Lake Cumberland near Monticello, KY. It is located approximately 175 yards from Old Fall Creek boat ramp. This is a Free boat ramp. No dock. If you should need to rent a boat, we are located close to the resorts at Conley Bottom and Beaver Creek. The cabin is known for being clean and comfortable. It is nestled among the trees next to land overseen by the Army Corp of Engineers. The area is always beautiful no matter what season. Come and Enjoy!!

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.

Beautiful Farmhouse near Lake Cumberland

This beautiful farmhouse has lots of amenities, 3 bedrooms, 2 bath. Coffee bar, Nice backyard with fire pit, Weber gas grill, 6 camping chairs to sit by the cozy fire and corn hole and basketball goal for added fun! Full front porch and nice quiet back porch. Laundry soaps, shampoo, propane, laundry detergent etc included. 4 flat screen TV’s. Activities for kids. Swing set, Located 5 minutes to Beaver Creek Marina , 15 minutes to Conley Bottom and less that 5 minutes to city limits.

HOT TUB~ Fire Pit~ KING Ensuites~ Lake Access

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.

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.