Holiday rentals with a patio 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.

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 time near the Falls, 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.

Cottagey-Cabin Private|Firepit~15% off July 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!

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.

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!☆

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.

Cozy Cumberland Lakeview Shangri-la

A fun, lake view lake house situated on the banks of the Big South Fork River. You will love waking up each morning with a beautiful view of the river. Watch as the boats go out for a day on the water. Every where you turn, you are surround with beauty. We back up to the Daniel Boon National Forest. No matter the time of year you decide to stay, there is always plenty of hiking, fishing and site seeing to do. We are also right across the street from the pool.

Welcome to your Dream Lake Home

Welcome to a place to forget your cares. This stylish home is perfect for family or group trips. Stunning lake views year round, 5 bedrooms/3 baths, games for kids or adults including foosball and ping-pong, a grilling area and full kitchen to prepare your catch of the day, a cozy electric fireplace, and a boat ramp less than 1 mile for easy access to all your water activites. Come see why they say "Lake life is the best life!"