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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.

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.

Vantage Point II

Come Relax with a stay at Vantage Point II. Enjoy breathtaking views, amazing sunsets and this beautiful three bedroom, two and a half bath, single level home. It overlooks the hang glider landing zone so you can watch the gliders and planes from the patio or raised porch! The home is well stocked and is located only 2 minutes from the flight park, 10 minutes from Cloudland Canyon, 10 minutes from Trenton, 10 minutes from Covenant College and 20 Minutes from the edge of Chattanooga (St Elmo).

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.

Glenn Falls Retreat

For nature-lovers, with a waterfall view during the wet season, and spectacular treetop views during the dry season, the Glenn Falls Retreat is ready to host your next mountain getaway! Only a 4 mile drive to downtown Chattanooga where you can enjoy some of the best restaurants, art and music in the south; and only 4 miles to Rock City and Ruby Falls; the Glenn Falls Retreat is on a 2 acre wooded lot where you can explore the Lookout Mtn. trails and the year-round majesty of Tennessee.

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

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.

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!

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.

Higher Ground

Take it easy at this unique and tranquil private apartment getaway as you enjoy mountain views and spectacular sunsets from your own private deck!! We are just minutes away from Rock City, Ruby Falls and over 25 miles of fantastic hiking and biking trails on the Cloudland Canyon Connector trail system. We are only 20 minutes from historic Southside Chattanooga where the vibe is fantastic. Come for a visit! We’d love to host you.

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.

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!!