Family-friendly holiday rentals in Lake Cumberland

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Top-rated family-friendly rentals in Lake Cumberland

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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An outdoor seating area is presented on a wooden deck overlooking a serene lake view. Comfortable furniture, including a sofa and chairs, surrounds a glass-topped table. An umbrella provides shade, and a small fire pit adds to the inviting space amidst greenery.
Home in Somerset
4.85 out of 5 average rating, 164 reviews

Lakeview Blue

You will not find a better view of Lake Cumberland! Newly renovated 2022!! Previously our family home, we cherish this property. We ask anyone renting to respect the neighbors and home as we have. The Lakeview Blue House is within walking distance of Lake Cumberland, several restaurants, gas stations and a liquor store. There is a seasonally open public boat ramp directly over the hill from the home and many others including Waitsboro, Burnside Marina and Burnside Island State Park/ ramp nearby.

Top guest favourite
A private dock extends over the tranquil waters, surrounded by lush greenery and towering trees. Stairs lead down from a rustic path, offering direct access to the lake. The clear water reflects the surrounding natural landscape, providing a serene setting.
Cabin in Bronston
4.87 out of 5 average rating, 118 reviews

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.

Top guest favourite
A covered deck area features comfortable seating and overlooks a lush landscape with a serene lake in the distance. Sunlight filters through the trees, illuminating the wooden flooring and creating a peaceful retreat for relaxation.
Tiny home in Monticello
4.94 out of 5 average rating, 259 reviews

Tiny LakeView Cottage~Pets Welcome! 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.

Top guest favourite
Cottage in Monticello
4.91 out of 5 average rating, 123 reviews

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!!

Top guest favourite
Home in Monticello
4.99 out of 5 average rating, 110 reviews

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!

Top guest favourite
Cottage in Monticello
5 out of 5 average rating, 110 reviews

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.

Top guest favourite
A charming cottage exterior is framed by lush greenery, featuring a welcoming red door with shutters. An American flag is displayed at the entrance, with a gravel path leading to the porch, which has wooden railings and a small seating area overlooking the natural surroundings.
Cabin in Burnside
4.9 out of 5 average rating, 101 reviews

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! ☆

Guest favourite
The exterior of a charming cabin is visible among a lush, wooded setting. The cabin features a metal roof and wooden sides, with a porch that invites relaxation. A blossoming tree adds a splash of color to the serene landscape, surrounded by green foliage.
Cabin in Monticello
4.92 out of 5 average rating, 128 reviews

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.

Guest favourite
A fully remodeled camper is positioned in a natural setting, surrounded by greenery. A cozy outdoor seating area with string lights, a dining area, and a grill is visible on the gravel surface. Two potted plants add a touch of nature to the space.
Camper van/Motorhome in Bronston
4.91 out of 5 average rating, 11 reviews

“Cumberland Lakeside Glampers”

“BRING YOUR BOAT, KAYAKS OR PADDLE BOARDS” Escape the hustle and bustle of life and work to “Cumberland Lakeside Glampers” Hidden away in the stunning hills of Echo Point on Lake Cumberland, the Glamper gives everything you need. Fully remodeled camper, with outdoor fire pit, grill and dining area. We have plenty of parking for your boat and vehicles. Echo Point boat ramp is less than a mile from the camper. Enjoy this stunning lake and coves with more coastline than Florida.

Top guest favourite
A spacious entryway features a striking artwork installation on the black wall, complemented by a spiral staircase leading to the upper level. Comfortable seating includes a tufted leather chair and a plush sofa, with a round wooden coffee table at the center on a decorative area rug.
Guest house in Somerset
4.98 out of 5 average rating, 218 reviews

Elegant Modern Rustic Retreat w/ Hot Tub

A steel framed industrial warehouse converted into an upscale two bedroom rustic-chic living space located within 8 miles of beautiful Lake Cumberland and within 5 minutes of Downtown, Somerset. The city is yours to explore from your own private 2 bed, 1 bath modern rustic retreat. Picture comfy beds, full bathroom, a kitchen built for entertaining, all under a metal tin roof for those rainy days when you just want to curl up and relax.

Top guest favourite
A shaded outdoor dining area features a table surrounded by chairs, set on a wooden deck. String lights hang overhead, and the expansive view of the lake and surrounding hills is visible in the background, enhancing the serene outdoor experience.
Home in Russell Springs
5 out of 5 average rating, 40 reviews

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!"

Top guest favourite
A charming cabin is nestled among trees, with sunlight streaming through branches. An American flag hangs by the entrance. A hot tub is located on a wooden deck, providing a serene spot to enjoy nature. The lake can be glimpsed in the background.
Cottage in Somerset
4.97 out of 5 average rating, 152 reviews

Cozy Lakehouse with a View

Imagine waking up in the morning to the birds chirping in the woods surrounding the cabin, fixing a cup of coffee, and relaxing on the deck that provides one of the best views you will ever experience on Lake Cumberland. This cabin is perfect for a romantic getaway, or a quiet retreat with the family. Simply put, this cabin offers memories that you will cherish for a lifetime and will talk about for years to come!

Popular amenities for Lake Cumberland family-friendly rentals