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Family-friendly holiday rentals in Dale Hollow Lake

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Top-rated family-friendly rentals in Dale Hollow Lake

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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
4.93 out of 5 average rating, 144 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, 252 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.

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, 342 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.

Guest favourite
A charming wooden cabin is set on a gently sloping green lawn, surrounded by tall trees. The cabin features a front porch with steps leading up to the entrance, and large windows are visible, providing a connection to the natural surroundings.
Cabin in Byrdstown
4.93 out of 5 average rating, 102 reviews

Cedar Ridge

Have a Lake Country getaway! Newly renovated, charming cabin with views of Dale Hollow Lake. One bedroom with queen size bed plus a queen size Murphy bed in living room. Enjoy a relaxing evening on the front porch after a fun filled day on the lake or exploring the area. The cabin has central heat and air for your comfort. Linens and towels are supplied. Full kitchen , laundry room has washer and dryer. Minutes from Star Point, Eagle Cove and Sunset Marinas. Enjoy this relaxing retreat!

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, 426 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
Cabin in Jamestown
4.93 out of 5 average rating, 181 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!!

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
4.93 out of 5 average rating, 246 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.

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, 271 reviews

Page's Legacy: Winter Hideaway at the Lake

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"

Guest favourite
A cozy tiny cabin is set amid a gravel area, surrounded by trees. A hammock is gently draped between posts, while wooden chairs are placed nearby. The cabin features a porch with a railing and string lights, extending a welcoming atmosphere.
Tiny home in Celina
4.97 out of 5 average rating, 115 reviews

Sunset Ridge Cabin- Snow Hill Farm

Our cozy tiny cabin is the perfect get away for your vacation. Come relax just 10 minutes from beautiful Dale Hollow Lake in our peaceful location here in Celina, TN. Our goal is to allow you to unwind and put a pause on the craziness of everyday life. Enjoy your cup of coffee with a view of our rolling hills pasture and farm animals. *All natural cleaning supplies used. Yay for a chemical free vacation!*

Top Guest favourite
A cozy living area features comfortable seating arranged around a wooden coffee table. A modern electric fireplace adds warmth to the space, while a large flat-screen TV is mounted on the wall. Natural wood accents create a welcoming atmosphere.
Cabin in Allardt
4.94 out of 5 average rating, 161 reviews

Equestrian Grandeur - w/ HotTub Lounge

Welcome to your new vacation! - Located in the Big South Fork White Oak Horse Community - Perfect Hot Tub Lounging Area - 60" Electric Fireplace - 65" Outdoor Roku TV - Outdoor Dine/Lounge - High-speed Wi-FI - Loft with Arcade Games & Movie Section - Fire Pit with Park Style Grill - Close to Hiking This property is perfectly located for those looking to explore the Big South Fork! Learn more below!

Top Guest favourite
A single-story home is set among lush green trees, featuring a metal roof and light blue siding. Windows are framed in burgundy, providing a contrast to the exterior. A gravel area surrounds the house, with wooden logs placed in the foreground, enhancing its secluded setting.
Cabin in Celina
4.93 out of 5 average rating, 109 reviews

Private getaway in the hills of Dale Hollow

Completely renovated, secluded home in the quiet hills of Dale Hollow. Perfect getaway for fishing, horseback riding, other water activities, or just to get away for some peace and quiet. Nearest marina is Holly Creek, just minutes away with multiple other options in the area. Close to horse trails and downtown Celina is a 10-15 minute drive with grocery stores, antique shops, and local restaurants.

Popular amenities for Dale Hollow Lake family-friendly rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top Guest favourite
A cottage is seen surrounded by vibrant autumn foliage, with a gravel driveway leading to the entrance. The architecture features a gabled roof and a spacious front porch, providing an inviting entry point to the home.
Home in Monticello
4.92 out of 5 average rating, 189 reviews

Bluegrass Gables: Lake Cumberland Cottage

Top Guest favourite
The exterior of a geodesic dome is featured, showcasing large panoramic windows and a wooden deck with steps. The dome is surrounded by greenery, providing a connection to nature. Clear skies and soft clouds are visible above, enhancing the serene atmosphere.
Dome in Albany
5 out of 5 average rating, 24 reviews

Luxury Dome • Hot Tub • Lake View • Near Marina

Top Guest favourite
A serene bedroom features a spacious bed adorned with soft linens and a decorative throw. Two windows allow natural light to fill the room, complemented by light-colored wood floors. Nightstands with lamps flank the bed, and subtle decor adds to the calming ambiance.
Home in Monticello
4.99 out of 5 average rating, 100 reviews

1/8 mi to boat ramp, SPA, FirePit, KING En-suites

Top Guest favourite
A cabin exterior is shown, featuring a wooden structure with a green metal roof. A welcoming front porch with multiple wooden railings is visible. An American flag is displayed, and surrounding trees with autumn foliage add warmth to the scene.
Cabin in Burkesville
4.98 out of 5 average rating, 62 reviews

Cabin w/boat parking 5 mins to State Park & golf

Superhost
The open living area showcases warm wooden walls and a spacious layout. A comfortable seating arrangement is positioned near a light-colored rug. The kitchen features modern appliances, while a dining setup is visible in the center. Stairs lead to the loft area, enhancing vertical space.
Cabin in Allons
4.85 out of 5 average rating, 27 reviews

Eagle’s Perch Cabin: Stay in the Heart of Nature

Guest favourite
A spacious cabin exterior is surrounded by well-maintained greenery and vibrant flowers. A large wraparound porch is visible, featuring wooden railings and a stone chimney. Tall trees and a clear sky provide a serene backdrop.
Cabin in Pickett County
4.89 out of 5 average rating, 19 reviews

Dale Hollow Lake Cabin

Top Guest favourite
A hot tub is positioned on a private porch, surrounded by lush greenery. A tray with a bottle of sparkling wine, two glasses, and fresh grapes is neatly arranged beside the tub. The scene conveys a serene and inviting atmosphere.
Cabin in Jamestown
4.98 out of 5 average rating, 126 reviews

The Treehouse TN Honeymoon Cabin HOT TUB - in BSF!

Top Guest favourite
A spacious green lawn extends toward the two-story Red Fox Inn, framed by mature trees. The inn features a red-roofed structure with white siding and a welcoming front porch. A nearby outbuilding adds charm to the tranquil setting, surrounded by ample open space.
Home in Baxter
4.98 out of 5 average rating, 223 reviews

The Red Fox Inn by Cummins Falls/Cookeville/Baxter

Family- and pet-friendly home rentals

Top Guest favourite
A cascading waterfall is surrounded by lush greenery, with water flowing over rocky ledges into a serene river pool below. The scene is illuminated by a warm, golden glow of the setting sun, creating a tranquil atmosphere amidst the natural landscape.
Guest suite in Cookeville
4.99 out of 5 average rating, 216 reviews

The Suite at Waterloo Falls- entire suite

Guest favourite
A covered deck features comfortable seating arrangements with a coffee table and a grill. Expansive views of the surrounding trees and Dale Hollow Lake are visible through open railing. The deck flooring is wooden, enhancing the outdoor experience.
Cabin in Celina
4.88 out of 5 average rating, 104 reviews

Dale Hollow Cabin

Top Guest favourite
An open living area features a cozy gray sectional sofa paired with a plush ottoman. Light wood paneling enhances the space, where a dining table sits nearby. A loft area with a bed can be seen above, with a staircase leading up for access.
Cottage in Celina
4.86 out of 5 average rating, 51 reviews

Beautiful cabin just seconds from Dale Hollow Lake

Top Guest favourite
An inviting structure resembling a general store features wooden siding and a covered porch. Rustic benches and log seating circle a gravel area, with trees providing shade. Vintage signage and decor enhance the entrance, which is framed by natural greenery.
Cabin in Monterey
4.98 out of 5 average rating, 541 reviews

Little Cabin in the Woods

Top Guest favourite
The cottage features a modern architectural design with a combination of brick and wood elements. A spacious deck extends from the front, complemented by outdoor seating arrangements. Large windows allow natural light to fill the interior, offering views of the surrounding greenery.
Home in Cookeville
4.98 out of 5 average rating, 336 reviews

New Modern Luxury Mountain Cottage

Top Guest favourite
A cozy living space is highlighted by a plush sectional sofa and a table with chairs. A flat-screen TV is mounted on the wall, facing a large window that allows natural light to fill the room. The ceiling features a rustic design, enhancing the inviting atmosphere.
Apartment in Livingston
4.97 out of 5 average rating, 159 reviews

A Fixer-Upper Style Place

Guest favourite
A comfortable living area features a sectional sofa covered in soft grey fabric, positioned on a patterned area rug. Natural light filters through a window dressed with patterned curtains, while a small side table rests beside the sofa. The entrance door stands in view, framed by a welcoming tone.
Home in Cookeville
4.88 out of 5 average rating, 221 reviews

Hilham House

Superhost
The cottage features a vibrant red metal roof and a welcoming porch with wooden chairs. A view of the surrounding area showcases greenery and buildings in the distance, including a clock tower, highlighting the cottage's proximity to the town center.
Cottage in Gainesboro
4.93 out of 5 average rating, 304 reviews

A vintage cottage in historic downtown Gainesboro

Family-friendly home rentals with a pool

Guest favourite
A heated pool is surrounded by lounge chairs beneath bright blue skies, with a shaded gazebo visible in the background. Poolside amenities include umbrellas and pool steps leading into the water, creating a relaxing environment for guests.
Tower in Russell County
4.87 out of 5 average rating, 23 reviews

Lake Cumberland State Park Villa

Guest favourite
The two-story building features a welcoming yellow entrance and expansive covered decks on both levels. A gravel driveway leads up to the property, with trees lining the background and a soft sunset sky providing a warm backdrop.
Home in Monticello
5 out of 5 average rating, 11 reviews

Cumberland Belle Lakehouse-5bedrm,10bed,5bath

Top Guest favourite
A charming two-story home is framed by trees, offering a peaceful setting. The entrance features a wooden staircase leading to double doors, with windows allowing natural light to brighten the façade.
Home in Celina
5 out of 5 average rating, 43 reviews

Farmhouse

Superhost
Guesthouse in Monterey
4.91 out of 5 average rating, 90 reviews

Tennessee Dream Getaway

Guest favourite
A cozy living area features a comfortable couch positioned towards a wall-mounted TV. A wooden coffee table sits in front, complemented by a small lamp and simple decorative items. The room is connected to a bright kitchen visible in the background.
Condo in Cookeville
4.81 out of 5 average rating, 171 reviews

Cozy Country Club Condo

Superhost
A well-appointed bedroom features a queen size bed with a light brown blanket and decorative pillows. Nightstands with lamps are positioned on either side. A patterned area rug is placed beneath the bed, and natural light filters in through a window adorned with blinds.
Condo in Cookeville
4.76 out of 5 average rating, 75 reviews

1 Bedroom Apt, Pet Friendly. Middle of Cookeville

Top Guest favourite
A modern living area features a light gray tufted sofa, arranged with accent pillows and a decorative throw. A wooden coffee table stands at the center, surrounded by a mix of seating options, including a leather armchair and a plush green chair. Shelves display decorative items and plants.
Home in Cookeville
4.95 out of 5 average rating, 101 reviews

Home on the Range

Guest favourite
A view of a two-story brown building with red doors, surrounded by lush green trees. A wooden walkway connects the units, offering a scenic outdoor space. The bright blue sky enhances the inviting atmosphere of the property.
Cabin in Jamestown
4.86 out of 5 average rating, 7 reviews

Lake Cumberland / Apple Valley Condo #K3