Family-friendly holiday rentals in Dale Hollow Lake

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Top-rated family-friendly rentals in Dale Hollow Lake

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

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Top Guest favourite

An outdoor seating area features two wooden adirondack chairs positioned beside a stone fireplace, where a welcoming fire is lit. Warm lighting highlights the wooden deck, and a small circular table rests nearby. A stack of firewood is neatly arranged against the wall.

Cabin in Jamestown

4.95 out of 5 average rating, 133 reviews

River Loft Cabin w Free Kayaks

* Waterfront cabin overlooking the lake. * Free kayaks: Kayak # 1: double sit-on-top ocean kayak. Kayak #2: single Pescador kayak. * Launch the Kayaks from the bottom of our ridge. * For boats: the boat ramp is 1/4 mile on Riverton Rd. * Wood burning outdoor fireplace on the open deck. Enjoy one of the 3 decks. Inside: * 3 queen beds, 1 bathroom, Central AC and heat, fresh bedding and towels, equipped kitchen. * Excellent WiFi at the cabin but cell service is spotty. Use WiFi calling.

Top Guest favourite

A spacious log cabin, surrounded by green landscaping, features a covered front porch supported by wooden columns. Rocking chairs are positioned on the porch, inviting relaxation. A stone fire pit is visible in the foreground, with a blend of wooded areas providing a natural backdrop.

Cabin in Allons

4.94 out of 5 average rating, 251 reviews

Sweet Southern Retreat near Dale Hollow Lake

Welcome to the Cox-Dean Family Cabin near beautiful Dale Hollow Lake. Enjoy the peace and tranquility of 17 acres of undeveloped land from the comfort of an updated and well-equipped log cabin. Features 3 bedrooms, a loft with 4 twin beds, 2 bathrooms, a full kitchen, a board game closet, charcoal grill, a smart TV and fiber/gig speed internet. Central heat/air and city water/sewer. **NEW KITCHEN APPLIANCES AS OF JULY 2025** NOTE: We do NOT have cable or satellite TV, only streaming services.

Guest favourite

A spacious living area features a modern sofa with decorative pillows. Large opening doors showcase views of the covered porch and surrounding greenery, allowing natural light to fill the space. A wall-mounted television and fireplace are also present, enhancing the inviting atmosphere.

Home in Somerset

4.95 out of 5 average rating, 130 reviews

Garage Door to the Wilderness!

Welcome to this stylish and sleek tiny home that's perfect for modern living! With ample space to sleep 4, features a bathroom complete with a beautifully tiled custom shower. The kitchen is a chef’s delight, black cabinetry and elegant granite counters.Enjoy the seamless flow of heated tile flooring throughout, leading you to the covered back porch where you can sip your morning coffee! The back garage door offers easy access to nature’s beauty. Located 5 minutes from either town or the lake!

Top Guest favourite

The farmhouse exterior features a welcoming porch with wooden railing and rocking chairs. Large windows allow ample natural light, while the surrounding trees create a serene setting. A wreath adorned front door adds a touch of charm to this early 1900's structure.

Farm stay in Allardt

4.92 out of 5 average rating, 333 reviews

Nancy's Nest -At Home on the Farm - 2 bedrooms

This quaint, early 1900's farm house sits among shady trees and overlooks a beautiful pasture and garden. Rock on the porch or roast marshmallows in the fire pit. The parking and turn around are big enough to accommodate a trailer. It's convenient to horse trails, hiking, kayaking, and biking on the beautiful Cumberland Plateau. Big South Fork National Recreation Area, Pickett State Park, Historic Rugby, Muddy Pond, and Sgt. Alvin C. York's Museum and Burial Place are all within 30 minutes.

Top Guest favourite

A cozy living area is highlighted by wooden walls and natural light. A dining table with chairs occupies one side, while a comfortable leather sofa with accent pillows faces a decorative fireplace. A chandelier hangs above, emphasizing the inviting ambiance.

Cabin in Moss

4.98 out of 5 average rating, 419 reviews

Tennessee Retreat Log Cabin Near Dale Hollow Lake

Tennessee Retreat Log Cabin, nestled in the hills of the Eastern Highland Rim, has everything you need to escape in style. Amenities (like WiFi and Cable TV) let you enjoy the serenity of the woods with casual or formal dining, antique or necessity shopping, water activities on Dale Hollow Lake - a 15 minute drive, wineries, historic & natural attractions & live entertainment. Perfect for business or pleasure trips, extended stay or hosting weddings or events on the extensive lawn. Welcome!

Top Guest favourite

A rustic cabin is framed by autumn foliage, featuring wooden siding and a welcoming sign. A small porch extends from the front, supported by wooden beams. A stone fire pit is visible in the foreground, alongside a single black chair resting on the ground covered in fallen leaves.

Cabin in Jamestown

4.93 out of 5 average rating, 176 reviews

River cabin on waterfalls BRING YOUR PETS!

Beautiful OFF GRID pet friendly cabin located on the Clearfork River. Over a mile of secluded river frontage and 4 SEASONAL waterfalls. Huge bluffs to explore. Large gated deck with picnic table and gas grill. Great place for you and your furry friends to hang out. This is OFF GRID, OFF ROAD, needing off road capable vehicle and adveturous outdoors loving people. This is not a cabin to send grandma in the Camary. {PLEASE READ ALL INFORMATION AND PHOTOS} Totally away from society!!

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

4.93 out of 5 average rating, 240 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.

Top Guest favourite

The exterior of a log home is shown, featuring a white door and a stone pathway leading to it. The rustic wooden siding highlights the natural textures. Surrounding greenery and trees frame the entrance, providing an inviting view of the property.

Farm stay in Lancing

4.96 out of 5 average rating, 171 reviews

Bunkroom at Fiat Farm

Tuck yourself into this cozy bunkroom attached to a custom-built log home. Situated on the site of a hundred-year-old homestead, this 67-acre property is now a regenerative farm. 10 minutes from Lilly Bluff overlook with hiking and rock climbing. A short drive to many Obed trailheads. Only 30 minutes to Frozen Head State Park. This space will be the basecamp for all your adventures. Or just enjoy the solitude as you explore the property and visit our farm animals. Welcome to Fiat Farm.

Guest favourite

A simple wooden tree house rests among the branches of a large oak tree, offering a rustic charm. Below, a picnic table is surrounded by two chairs, set on a grassy lawn. The area is open and inviting, under a clear blue sky.

Cabin in Rugby

4.92 out of 5 average rating, 120 reviews

A Little Closer to Heaven Primitive Tree house

This little tree house is primitive with no electricity and no water but has a bath house nearby. This is tent camping in a tree house. Located behind the historic R.M. Brooks Store, it is the perfect place to find peace and beauty . Perfect for hikers. Rest in the huge branches of this nearly 100 year old Oak Tree. A Queen bed awaits you for your restful nights sleep. Underneath you can picnic at the table or swing in the swing that hangs below. This is the perfect place to unplug.

Superhost

A cozy bedroom features a king memory foam mattress adorned with soft blankets and decorative pillows. A stylish rug lies beneath, while wall art consisting of wooden paddles adds a nautical touch. A bedside lamp and small side table provide practical accents.

Apartment in Monroe

4.86 out of 5 average rating, 110 reviews

Captain's Cove, Lakeside Inn at Dale Hollow

The Lakeside Inn at Dale Hollow is the perfect getaway for families, outdoor adventurers, and lake lovers. Newly renovated in 2021 the Captain's Cove king room offers a cozy king memory foam mattress, coffee bar, highspeed internet, smart tv, and amenities all in a stylish and clean space. Located 3/4 of a mile from Sunset Marina guests can experience all that Dale Hollow Lake and the Obey River Recreational area have to offer. Local tips and recommendations can be found in your room!

Top Guest favourite

A small dining area is positioned in front of large windows, offering a view of the lake at sunset. A bottle and glass sit on the table, which is flanked by two benches. The warm hues of the setting sun fill the room.

Guest suite in Albany

4.97 out of 5 average rating, 269 reviews

Page's Legacy: Favorite Fall Getaway

All rooms have a view of the lake and the deck overlooks Dale Hollow. We are a mile from Wolf River Boat Dock. The suite is downstairs with a private entrance. There are walking paths that encompasses 3 acres on the property. The private deck has a fire pit for chilly mornings to enjoy coffee or relaxing evening. There are some great day trips I have added to the "Host Guidebook" Click on "More about this location" and scroll to the bottom and click on "Show Host Guidebook"

Top Guest favourite

A serene country road is flanked by vibrant autumn trees showcasing orange and gold leaves. A quaint cottage with a green roof is partially visible, nestled among the foliage and softly illuminated by natural light.

Cottage in Hickman

4.96 out of 5 average rating, 779 reviews

Gibbs Farm Cottage; Kids and Pets Welcome

Our motto is: Clean, convenient, comfortable and affordable. High speed fiber optic Internet/WIFI. Pet/kid friendly. Plenty of parking, five miles off I-40. Located on a 68-acre working farm, the cottage sits in a peaceful valley surrounded by rolling hills, pastures and woods. Relax and enjoy the tranquility of the country. Get a taste of farm life. Or enjoy outdoor activities available in the area. Come enjoy our little piece of heaven!