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.

Indoor spacesFamilyHeating

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 spacesLayout

4.99 out of 5 average rating, 381 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.

FamilyKitchenAccuracy

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.

KitchenIndoor spacesView

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 spacesFamilyDecor

4.95 out of 5 average rating, 227 reviews

4.92 out of 5 average rating, 263 reviews

A spacious living area is highlighted by large windows that offer expansive views of the surrounding landscape. Comfortable leather seating is arranged around a wooden coffee table, with a decorative rug beneath. Natural light floods the room, accentuating the home's warm color palette.

Home in Rising Fawn

Vantage Point

*newpaved driveway* *new mattresses* (added after recent review) Come experience life at the "Vantage Point"! This cozy home with amazing views is located less than ten minutes from Cloudland Canyon State Park and is less than half a hour from downtown Chattanooga! With both an upper and lower deck, there's plenty of space to soak up the sun, enjoy the view and even see a hang glider or two! You can't ask for much more! Comfy Beds in a Cozy Convenient Home with Breathtaking Views!

FamilyIndoor spacesCondition

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 spacesFamilyView

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.

Indoor spacesKitchenCleanliness

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

Our adorable lakefront cabin with breathtaking views of Lookout Mountain and Johnson Lake. Enjoy swimming, kayaking, hiking, caving, fishing — right in your backyard! Inside you'll find a full kitchen, full bathroom, queen bed + sofa bed and cot too. Plus, pet-friendly! Must-Dos: - Cloudland Canyon (15 min away) - Wilderness Outdoor Movie Theater (15 min) - Lookout Hang Gliding (20 min ) - Downtown Chattanooga (20 min) - Ruby Falls (25 min) Book today!

FamilyKitchenSleep quality

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.

Indoor spacesKitchenLocation

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

Oliver and Lacey (the cats) would love to welcome you to Our Catty Shack! ***NOTE: Our Catty Shack comes WITH indoor/outdoor CATS*** This spiritual retreat is nestled between imposing ridgelines, abuts a state forest, and faces the powerful Tennessee river. Enjoy dramatic sun and moon rises. Luxuriate in the hot tub. Feast your eyes on the views. Only 15 minutes to downtown Chattanooga - with the peace of the country - have it all here.

FamilyIndoor spacesCheckout

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 spacesKitchenBackyard

4.99 out of 5 average rating, 101 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

Cabin in Lookout Mountain

Lookout Lazy Bear Cabin

Indoor spacesKitchenBarbecue

4.95 out of 5 average rating, 295 reviews

Bungalow in Lookout Mountain

The outdoor porch features two hanging swinging chairs and a cozy loveseat, surrounded by lush greenery. Natural light filters through large glass doors, enhancing the serene atmosphere. The wooden deck provides a rustic touch, inviting relaxation while enjoying the peaceful views of the surrounding woods.

Free Ruby Falls Ticket & More-Treehouse-Hot Tub

KitchenIndoor spacesBathroom

5.0 out of 5 average rating, 109 reviews

5.0 out of 5 average rating, 213 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

FamilyKitchenView

Superhost

Cabin in Bryant

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

Indoor spacesKitchenCleanliness

4.89 out of 5 average rating, 233 reviews

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 spacesFamilyComfort

4.97 out of 5 average rating, 152 reviews

4.85 out of 5 average rating, 576 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

Indoor spacesKitchenCondition

4.96 out of 5 average rating, 461 reviews

A luxurious hot tub equipped with spa jets and water lights is positioned on a spacious deck, surrounded by colorful autumn foliage. String lights are draped overhead, casting a soft glow, while a fire pit and seating area are visible in the background.

Cabin in Whitwell

Hillside Haven | Hot Tub | EV | Firepit | Cornhole

KitchenIndoor spacesLaundry

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

FamilyKitchenTV

Family- and pet-friendly home rentals

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 spacesFamilyHospitality

4.9 out of 5 average rating, 163 reviews

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

Indoor spacesFamilyCheckout

4.95 out of 5 average rating, 365 reviews

Riverfront Getaway with a View

KitchenIndoor spacesValue

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

KitchenFamilyHospitality

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

KitchenIndoor spacesWalkability

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 spacesFamilyView

4.96 out of 5 average rating, 161 reviews

Two individuals stand side by side, each holding an animal. One person is holding an alpaca, displaying its soft, fluffy wool. The other person is positioned closer to a donkey, which is visible in the foreground. The scene is set against a natural backdrop with warm sunlight.

Farm stay in Rock Spring

Little House on the Farm

KitchenIndoor spacesSleep quality

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

Indoor spacesFamilyCheck-in

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

FamilyIndoor spacesWalkability

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!

FamilyKitchenView

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

FamilyIndoor spacesNearby

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

Indoor spacesFamilyNearby

4.99 out of 5 average rating, 228 reviews

Townhouse in Chattanooga

1424 Stockyard-Kid Fav Chatt-town-Sleeps 9

KitchenFamilySleep quality

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 spacesComfort

4.95 out of 5 average rating, 102 reviews

Home in Menlo

Scenic A-Frame | Pool, Hot Tub & Panoramic Views

Indoor spacesKitchenAir conditioning