Family-friendly holiday rentals in Lookout Mountain

4.98 out of 5 average rating, 331 reviews

The treehouse exterior is framed by vibrant autumn leaves, showcasing a wooden structure with large windows and ornate details. A wooden walkway leads to a charming entrance, warmly lit by ambient lights that create a welcoming atmosphere at dusk.

Treehouse in Trenton

Whippoorwill Retreat Treehouse

“Escape, Relax, & Write Your Own Story” **NO SERVICE FEES** Whippoorwill Retreat is a romantic, family-friendly real treehouse in the treetops 20 minutes from Chattanooga. This peaceful escape offers floor-to-ceiling views, a sunrise perch, outdoor fireplace, fire pit for lazy nights, and outdoor soaking tubs with Whippoorwill-scented salts, Alexa for music, and a chandelier. Sleep in a suspended bed or the Canopy Suite, a view of the stars awaits. Write your fairytale at Whippoorwill Retreat.

FamilyIndoor spacesNearby

4.99 out of 5 average rating, 120 reviews

A serene outdoor area features a sparkling pool, surrounded by vibrant autumn foliage. Adirondack chairs are positioned along the poolside, facing the horizon. The sun sets in the distance, casting warm hues across the sky and reflecting on the water, enhancing the tranquil atmosphere.

Home in Lookout Mountain

Lookout Mountain Retro Pad - last booking Nov ‘26

📅 Last date to book: November 2026 as we are wrapping up our “hosting career”! It’s been a pleasure to meet & host others, and we look forward to our last couple months! 🏡 Mid Century bluff home with views of the rolling Georgia and Tennessee mountains. Open kitchen floor plan, natural light, and four bedrooms to comfortably accommodate up to 6 guests (up to 8 for immediate family). We are best suited as a QUIET & peaceful retreat. We are located in a full time residential neighborhood.

FamilyIndoor spacesHiking

4.99 out of 5 average rating, 382 reviews

The rustic cabin features a wooden exterior with a traditional gable roof, surrounded by trees. A welcoming porch is equipped with two chairs, and the cabin entrance is highlighted by a vintage door. Natural stone steps lead up to the porch area.

Cabin in Wildwood

Tadpole Cabin at Creek Road Farm

Nestled atop a hill on 60 pastoral acres in Wildwood, Georgia, this charmingly rustic one room cabin makes for an ideal family basecamp for local adventures or a romantic couples getaway. The cabin is newly constructed from 150 year old barn timbers and surrounded by shady forests and open pastures. The rest of the world may feel far away, yet Tadpole is only minutes from downtown Chattanooga, Cloudland Canyon State Park and most other area attractions. The perfect escape from everyday life.

FamilyIndoor spacesParking

4.99 out of 5 average rating, 159 reviews

The zome structure features a unique geometric design with large, faceted glass panels that reflect the surrounding greenery. Steps lead up to a wooden deck, with a wooden storage area for firewood visible near the entrance. Nature envelops the home, enhancing its secluded setting.

Dome in Rising Fawn

The Laurel Zome - Wood Fired Japanese Hot Tub

Acres of nature surround and insulate your moment of rest here at the Laurel Zome. With intriguing geometry drawn directly from the architecture of mountain laurel blossoms, pangolin scales, and pinecones—the simplicity and focus of the zome allows a lofty experience. Wake to natural light spilling in from expansive faceted windows and skylights. Enjoy the ritual of stoking a fire to prime your body to slip into downy sheets for sleep, or into to the waters of your Koto Elements spa tub.

Indoor spacesKitchenLocation

Chalet in Lookout Mountain

The cabin, constructed from logs, is nestled among tall trees highlighting a warm, rustic aesthetic. A spacious deck wraps around the front, featuring seating for relaxation. The peaked roof enhances the structure's charm, while vibrant fall foliage surrounds the peaceful setting.

Cabin at Wayside - on Lookout Mtn, close to city!

The Cabin at Wayside is located on wooded Lookout Mountain in Wayside Estate, less than a half-mile from Covenant College and just a 10- minute drive from Chattanooga. Offering privacy and quiet in what is described as a luxury tree house, the cabin is surrounded by miles of biking and hiking trails. The cathedral ceiling and windows create a cozy living, dining and cooking area. A main floor bedroom and sleeping loft make the cabin perfect for couples, friends and small families.

Indoor spacesKitchenRiver

4.95 out of 5 average rating, 227 reviews

4.98 out of 5 average rating, 311 reviews

A spacious hammock is suspended between wooden posts on a deck, presenting an unobstructed view of the valley below. The sky is adorned with clouds reflecting the warm hues of sunset. Large windows of the cabin are visible, enhancing the connection to nature.

Home in Lookout Mountain

The Lookout Mountain Birdhouse

Welcome to the Lookout Mountain Birdhouse! This modern cabin in the woods (completed in 2021) is surrounded by stone, trees, and a breath taking view! This house was built to stretch towards the clouds with a 1000 sqft deck and bird's eye view from inside. The 8 foot windows allow for an unobstructed view. The sunset facing view and valley below offer pure relaxation. Watch out for hang gliders and eagles- they love to fly by! Whatever your reason for visiting, this place has it

Indoor spacesKitchenHeating

4.96 out of 5 average rating, 869 reviews

A yurt stands on a spacious deck, surrounded by trees and breathtaking mountain views. The structure features a rounded top with a domed skylight, and the clear sky enhances the natural scenery in the background.

Yurt in Rising Fawn

Maple Yurt Lookout Mountain Chattanooga Glamping

Take advantage of all the activities Lookout Mountain has to offer, from breathtaking hikes and scenic drives to a variety of local attractions. From the Rock City Gardens to the Incline Railway, you’ll find plenty of ways to explore and enjoy the natural beauty of the area. With our yurts, you can relax in comfort and style with all the comforts of home. Enjoy a romantic dinner on the deck overlooking the breathtaking view or just relax and make the most of your time together.

FamilyIndoor spacesWalkability

5.0 out of 5 average rating, 180 reviews

A charming log cabin with a green metal roof is set among lush greenery. A spacious porch, adorned with string lights, invites relaxation. Stone pathways lead to the entrance, framed by well-maintained hedges and decorative boulders, creating an inviting first impression.

Cabin in Rising Fawn

Sunset views, FirePit, Pond Fishing, Hot Tub

Escape with family and friends to “Little Cabin on the Farm,” where the hardest choice you’ll make is how to relax. Read or nap on the porch swing, fish for rainbow trout, bass, or brim, stroll by the pond, or watch the sunset by the outdoor fireplace or fire pit. Grill and dine inside or out, unwind in the hot tub, or enjoy games and cornhole. Need more room? Check our profile to book “Little Barn on the Farm,” which sleeps 6 more guests.

KitchenIndoor spacesAccuracy

Guest suite in Lookout Mountain

A scenic outdoor space features a fire pit surrounded by natural stone and a picnic table. Lush greenery and colorful flowers enhance the landscape, while a person stands admiring the expansive view of valleys and distant mountains against the backdrop of a vibrant sunset.

Peace Inn on Lookout Mtn.

More than just captivating views, this place has Presence, Magic and Heart. It’s also immaculately clean, has well-appointed amenities and unique self therapies… all to guide you to your inner most quietude - a gift to take with you for the rest of your days. Perfect for personal retreats, weekend getaways, life celebrations or a relaxing home base after enjoying area offerings. Why "peace out" when you can Peace Inn?

Indoor spacesKitchenOutdoor spaces

4.99 out of 5 average rating, 101 reviews

Tiny home in Lookout Mountain

A compact living area features a spacious bed alongside a cozy sofa, with light streaming through large windows. Natural wood paneling creates a warm, inviting space. Kitchen amenities are integrated into the design, showcasing a sink and counter area, adding functionality to the interior.

3 Oaks Tiny Home Escape on Lookout Mountain

Welcome to 3 Oaks -- experience tiny home living in a BRAND NEW, award-winning, Escape Boho, at the heart of Lookout Mountain. Just off Scenic Highway, you'll be minutes from everything the mountain has to offer: Hang Gliding Park (5min), Lula Lake Land Trust (6min), Covenant College (8min), Rock City (12min), Ruby Falls (19min), Cloudland Canyon State Park (15min), downtown Chattanooga (26min)

Indoor spacesFamilyTV

4.98 out of 5 average rating, 303 reviews

Cabin in Lookout Mountain

The cabin presents a two-story structure surrounded by trees, with large windows offering natural light. A deck extends from the front, providing outdoor space beneath the shade of greenery. A stone foundation is visible, contributing to the rustic charm of the building.

The Magic Treehouse

Cozy and spacious cabin at the top of Lookout Mountain, GA. Enjoy the woodsy scenery and outdoor activities around Lookout. Close to hiking and biking trails, hang gliding, rock climbing, and many other outdoor activities. It is only 20 minutes from downtown Chattanooga. There is plenty of room on both decks for bikes or hang gliding equipment and anything else you might want to bring.

Indoor spacesKitchenCheck-in

4.98 out of 5 average rating, 447 reviews

Cabin in Lookout Mountain

Lookout Lazy Bear Cabin

Looking for a family or group of friends get away but close to Chattanooga, Rock city and Ruby Falls?? This is a cozy cabin in the woods away from everyone but close to everything! There is plenty to do outdoors! hiking, mtn biking, rock climbing, to name a few. The cabin is totally DISINFECTED and SANITIZED after each guest leaves for your safety. Come relax at our Lazy Cabin!!

KitchenFamilyPets

4.95 out of 5 average rating, 295 reviews

Popular amenities for Lookout Mountain family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

The exterior of a modern cabin is showcased at sunset, featuring a metal roof and large windows. The structure is surrounded by greenery and dramatic rock formations, with warm lights illuminating the porch area, creating a welcoming ambiance facing the Tennessee River and mountain views.

4.97 out of 5 average rating, 330 reviews

Our Catty Shack

Indoor spacesFamilyLayout

Holiday home in Rising Fawn

A fire pit is surrounded by stones, with flames dancing above a wooden log. In the background, warm string lights illuminate a fenced outdoor area, and wooden seating is positioned nearby on green grass.

Cloudland Arbor. Rooted in Nature

Indoor spacesFamilyBackyard

4.97 out of 5 average rating, 152 reviews

5.0 out of 5 average rating, 214 reviews

A rustic grain bin structure is featured with a covered porch and wooden overhang, set against an evening sky. A well-maintained pathway leads to the entrance, flanked by landscaped gardens. Cozy seating areas can be seen on the porch, inviting relaxation in serene surroundings.

Cabin in Chickamauga

Unique Silo -Peaceful Country Setting with Mountain Views

KitchenFamilyHospitality

Superhost

Cabin in Bryant

Big Time Hill Cabin with an indoor pool, hot tub,

Indoor spacesFamilyLocation

4.89 out of 5 average rating, 233 reviews

An outdoor deck overlooks expansive views of the surrounding landscape at sunset. A private pool is situated beside the deck, with lounge chairs arranged for relaxation. The home features an inviting structure with warm lighting, enhancing the tranquil evening setting.

4.9 out of 5 average rating, 423 reviews

Sunset Haven 4BR + Pool + Hot Tub + Fireplace

KitchenIndoor spacesRiver

4.85 out of 5 average rating, 577 reviews

The exterior of the hand-carved cave cottage is presented at dusk, with soft lighting highlighting the entrance. Lush greenery and colorful flowers surround the stone pathways, while the gentle slopes of the hill and distant mountains provide a scenic backdrop.

Bungalow in Wildwood

The Cavern Cave Cottage w/ Hot Tub & Scenic Views

KitchenFamilyAccess

4.91 out of 5 average rating, 162 reviews

A treehouse structure is elevated on a wooden platform, featuring a green slide that descends into a ball pit filled with colorful foam shapes. Ambient lighting is provided by a large chandelier above, adding to the playful atmosphere.

Apartment in Rock Spring

Theater & Treehouse Arcade at Rock Spring Resort

FamilyIndoor spacesBathroom

The backyard features a spacious layout with a five-person hot tub and blue Adirondack chairs arranged around a small fire pit. String lights overhead create a warm ambiance. The home is positioned above, with a deck accessible by steps.

4.97 out of 5 average rating, 186 reviews

Chattanooga 4BR: Pool, Hot Tub, Fire Pit, Near DT

Indoor spacesKitchenCheck-in

Family- and pet-friendly home rentals

4.94 out of 5 average rating, 174 reviews

A cozy interior showcases warm wood paneling, with a spacious sofa and coffee table in the sitting area. A decorative quilt with floral patterns covers the bed. A wall-mounted fireplace adds warmth, and a large window brings in natural light.

Cabin in Rising Fawn

Adorable Lakeside Lookout Cabin - Water/Mtn Views

Indoor spacesKitchenAir conditioning

4.98 out of 5 average rating, 100 reviews

An inviting outdoor space features a wooden deck illuminated by natural light. Two circular, cedar sleep pods are positioned in the background, alongside a stylish stone table with a decorative plate. Comfortable seating and a gas grill can be seen, complemented by trees in the setting.

Treehouse in Wildwood

Private Treehouse & Sleep Pods with Amazing Views

KitchenFamilyBathroom

Cabin in Lookout Mountain

The cabin's exterior features a charming wooden facade with a sloped roof, complemented by a front porch lined with rocking chairs. A spacious driveway leads to the cabin, surrounded by lush greenery and mature trees, providing a serene, natural setting.

Lookout Mountain Valentine Drive Cabin 1

Indoor spacesFamilyAir conditioning

4.9 out of 5 average rating, 163 reviews

4.95 out of 5 average rating, 365 reviews

Riverfront Getaway with a View

KitchenIndoor spacesHiking

A remodeled farmhouse exterior is showcased, featuring a white façade and a welcoming porch with wooden columns. Large windows allow natural light to illuminate the entrance. The landscaped yard includes green grass and a stone border, complementing the serene neighborhood setting.

4.97 out of 5 average rating, 543 reviews

Boutique St Elmo Farmhouse 7 min from Downtown

KitchenFamilySleep quality

4.94 out of 5 average rating, 338 reviews

A fire pit is surrounded by five blue chairs, set against a backdrop of trees with autumn foliage. The cabin is visible in the distance, with warm light glowing from the windows, creating a cozy atmosphere in the serene outdoor setting.

Cabin in Trenton

Secluded Country Cabin between city and country

KitchenFamilyCheck-in

A charming front porch is showcased, framed by lush greenery and soft lighting. The entrance features a wide, welcoming pathway leading to the door, while the spacious yard and fenced area provide a sense of privacy and openness.

4.93 out of 5 average rating, 1054 reviews

Bring the Pets 3 bed/1.5 bath Close to Everything

KitchenIndoor spacesGetting around

The charming exterior of a white home features a welcoming porch surrounded by lush greenery. A well-manicured yard with blooming plants enhances the inviting atmosphere. The traditional architectural details, including a gabled roof and decorative trim, are complemented by large windows allowing natural light.

5.0 out of 5 average rating, 187 reviews

St. Elmo Farmhouse - Historic Charm 3Bd/3Ba

Indoor spacesKitchenAmenities

Family-friendly home rentals with a pool

Superhost

A clear blue pool is framed by a wooden deck, with steps leading into the inviting water. Surrounding greenery offers a natural backdrop, and sunlight glints off the surface, creating a serene environment for relaxation.

Home in Chattanooga Valley

Chatt Vistas Oasis|3bdrm|5mtoTN|PoolDeckBBQFirePit

FamilyKitchenWi-Fi

4.89 out of 5 average rating, 184 reviews

Superhost

A spacious living area features a large stone fireplace, surrounded by comfortable seating on light-colored sofas. Towering floor-to-ceiling windows provide abundant natural light and stunning views of the forested outdoor landscape. A round coffee table sits at the center, adding a welcoming touch.

Cabin in Rocky Face

Quiet A-frame cabin w/pool ~ perfect for families!

KitchenIndoor spacesView

4.79 out of 5 average rating, 244 reviews

4.92 out of 5 average rating, 107 reviews

Cabin in Bryant

Fish Tales Cabin – Spacious Retreat with Hot Tub

FamilyKitchenNearby

4.99 out of 5 average rating, 228 reviews

Townhouse in Chattanooga

1424 Stockyard-Kid Fav Chatt-town-Sleeps 9

FamilyKitchenBathroom

A spacious master bedroom features a large bed with neutral bedding, complemented by decorative pillows. A striking wall mural of tropical leaves serves as a focal point. Two bedside lamps provide ambient lighting, alongside a small side table and a desk in the corner. Natural light enters through double doors leading to a private covered balcony.

4.98 out of 5 average rating, 168 reviews

Riverwalk Retreat• Spacious• Pool • 5 min>Downtown

FamilyIndoor spacesCheck-in

A modern open-concept living space displays a foosball table in the foreground, leading into a stylish kitchen and dining area. Bold artwork featuring a butterfly adorns the wall, complemented by vibrant lighting and a mix of contemporary furniture in soft hues.

4.99 out of 5 average rating, 128 reviews

Sauna | Game Room | Chef's Kitchen | EV Charger

KitchenIndoor spacesBreakfast

4.91 out of 5 average rating, 371 reviews

A modern kitchen features a large granite countertop with bar seating for four, stainless steel appliances, and white cabinetry. Natural light enters from the balcony doors, creating a welcoming atmosphere. An open floor plan connects the kitchen to a cozy sitting area with comfortable furnishings.

Condo in Chattanooga

409~WALK TO AQUARIUM~2BR/2BA~Luxury Downtown Condo

Indoor spacesFamilyRiver