Holiday houses in Lookout Mountain

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.

Location · Value · TV

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.

Family · Location · Comfort

Lookout Mountain Retreat | Hot Tub, Sauna & Views

Beautifully appointed, spacious home atop Lookout Mountain with stunning bluff views. Sleeps 10 with 2 king and 1 queen bedrooms and 2 trundle beds. Enjoy 3.5 baths, including a master bath with sauna. Full kitchen, dining area, wet bar, fireplaces in master and living room. Relax on the large back deck with hot tub and patio seating. Backyard includes fire pit and open space—perfect for gatherings. Includes laundry room and extra storage. Ideal for a mountain escape! NO PETS ALLOWED!******

Location · Family · View

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.

Location · Value · Indoor spaces

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!

Location · Family · Hospitality

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

Value · Location · Hot tub

Mountain Tree House

Life amongst the trees on Beautiful Lookout Mountain. This 4 story container home is super unique and beautiful ! The main house has 3 bedrooms and 3.5 baths, also there is a detached guest cottage . The master bedroom is 13’x40’ and on the 3rd floor. Take a bath and lookout at the beautiful view. The master deck has a putting green with 2 cups. The 4th floor library is a wonderful place to relax. The 5th floor observation deck puts you in the tree tops with a putting green and cup.

Family · Location · Parks

The Fox Lair Cottage @ Cloudland Canyon

Kick your shoes off and relax looking out over the amazing views from Fox Lair Cottage. Take a hike through Cloudland Park and then come back to the cottage to enjoy your favorite beverage while gazing off into the sunset. The Fox Lair Cottage has everything you need for a wonderful getaway. Whether you are coming to town for golfing at McLemore, hiking through Cloudland Canyon, or hang gliding off Lookout Mountain, you won't want to leave. You won't be disappointed by the views!

Family · Location · View

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.

Family · Location · Breakfast

A-Frame Independence by Red White and Blue Views

Escape to a one-of-a-kind stay on Lookout Mountain - a new A-frame cabin set on 75 private acres, designed for relaxation and connection. Whether you're sipping coffee as morning fog rolls through the valley or watching hang gliders at sunset, this is the kind of place you don’t forget. Perfect for families, couples, and small groups, this cabin blends modern design with natural beauty—giving you space to slow down, spread out, and truly enjoy where you are.

Family · Location · Sleep quality

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.

Family · Value · Quiet

Lookout Escape | Hot Tub + Mtn Retreat by RW&BV's

Tucked into the desirable Fairyland neighborhood on Lookout Mountain, this spacious retreat is minutes from Rock City, Ruby Falls, and downtown Chattanooga. This signature stay by Red White and Blue Views is designed for groups, it features two living areas, a large kitchen, and plenty of room to spread out. Relax in your private 5-person hot tub or unwind on the wraparound deck surrounded by peaceful woods.

Location · Family · Decor