Vacation rentals in Wayne County

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Top-rated vacation rentals in Wayne County

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Top guest favorite
An outdoor seating area is arranged around a fire pit, with chairs positioned for comfort. The night sky glows softly from the moonlight, casting a gentle light on the surroundings. Trees are faintly visible in the background, enhancing the serene atmosphere.
Home in Bronston
4.99 out of 5 average rating, 165 reviews

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.

Top guest favorite
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
4.86 out of 5 average rating, 111 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 favorite
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, 257 reviews

Tiny LakeView Cottage~Pets! 1 nights available

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.

Guest favorite
A charming cottage is nestled among greenery, offering a welcoming porch with seating. The roof is designed with a warm red hue that complements the natural surroundings. The mountains in the background provide a serene view, enhancing the outdoor atmosphere.
Home in Whitley City
5 out of 5 average rating, 7 reviews

Lake Cumberland Forest Cottage!

Cumberland Lake Cottage gives convenient access to all the best hikes and scenery! Located in Daniel Boone National Forest in McCreary County on a perfect Lake Setting! Close to all the major attractions while offering a peaceful, relaxing, outdoor kind of stay. Enjoy the Natural Arch…Lick Creek Falls…Cumberland Falls (with horseback riding) and Big South Fork Scenic Railway for an unforgettable train ride! Direct access to Lake Cumberland for swimming, fishing, boating and floating!

Top guest favorite
The cabin exterior is enveloped by lush greenery, featuring a welcoming wooden deck with a railing adorned with potted plants. Large glass doors invite natural light, complemented by multiple windows that enhance the warm, woodsy atmosphere of the structure.
Cabin in Monticello
5 out of 5 average rating, 24 reviews

Cottagey-Cabin, Private~Firepit! July Books Fast!

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 of CONLEY BOTTOM MARINA from its secluded, private, 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!

Top guest favorite
Home in Monticello
4.99 out of 5 average rating, 109 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 favorite
Cottage in Monticello
5 out of 5 average rating, 108 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.

Guest favorite
The cabin entrance is framed by a wooden ramp leading to a covered porch. A picnic table is positioned on the grassy area beside the porch, providing an outdoor seating option. A privacy fence surrounds the yard, creating a secluded space.
Cabin in Monticello
4.96 out of 5 average rating, 26 reviews

D&D Cabin at Lake Cumberland *Pets Welcome*

Our cabin is a cozy place to relax and enjoy with the whole family. It is centrally located in Monticello, Ky. There is 2 parking areas to accommodate guest and boat parking. We are 5 minutes from Walmart and Black Stallion Steakhouse. Conley Bottom and Beaver Creek Resort is within 15 minutes. Nearby are multiple docks for fishing. We have an outdoor grill and picnic table with privacy fence. Marina Rowena is 28 minutes away. As well as Safe Harbor Marina is 25 minutes from here.

Guest favorite
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, 123 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.

Top guest favorite
Cabin in Monticello
5 out of 5 average rating, 29 reviews

Hidden Creek Schoolhouse

Not all escapes are found on maps; some are found in time. Tucked into a quiet hollow just about 20 minutes from Dale Hollow Lake and Lake Cumberland, this 1919 schoolhouse offers a slower summer rhythm. Sunlight filters through original wood floors, the seasonal creek hums nearby, and fireflies dance at dusk. Spend your days on the water, then return to stillness. Hidden Creek is a storybook stay you step into, not rush through. Evenings stretch long under starlit skies.

Top guest favorite
An outdoor deck area features a wooden table complemented by an orange lantern and a rustic gray lantern. Lush green trees provide a natural backdrop, and a glimpse of the lake is visible in the distance under a clear blue sky.
Home in Wayne County
4.95 out of 5 average rating, 57 reviews

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.

Guest favorite
A spacious living area features a sectional sofa with a checked throw, a spiral staircase leading to a loft, and a hanging hammock chair. A ceiling fan provides ventilation, and large windows allow natural light to fill the room. A recliner is positioned for comfortable seating.
Cabin in Wayne County
4.93 out of 5 average rating, 85 reviews

Secluded Cabin on 18 Acres Near Lake Cumberland

Important Notice: No Hunting Permitted. Take it easy at this tranquil cabin on a private 18-acre farm—just 10 minutes from Conley Bottom Resort and Burnside Island. Enjoy the fire pit, peaceful wooded paths, and full privacy. Nearby attractions include restaurants, lake views, hiking, a Wildlife Management Area, kayak rentals, a 3D archery range, bowling, mini golf, and more. The perfect mix of seclusion and fun near Lake Cumberland.

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