Holiday houses in Lookout Mountain

Ray's Place w/ Mountain Views on Lookout Mountain

From the back deck you can see 3 states! Gigabit wifi is freely available to all guests, along with Fiber Optic 4K HD TV, fireplace, outdoor fire pit, BBQ grill, 2 full bathrooms, 3 beds, nice kitchen with brand new appliances, BOSE surround sound for incredible movie watching, washer & dryer, and a million-dollar view. Chattanooga 20 minutes, Cloudland Canyon, Rock City and hang gliding all within 5-13 minutes. Very safe area, & onsite security. Undeclared guest fee of $50 per night for each un

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.

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.

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!

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 Lodge at Live A Little Chatt | Unreal views

Breathtaking mountain retreat perched on Lookout Mountain’s west-facing brow. “The Lodge at Live A Little Chatt” offers mesmerizing sunset vistas, a spacious loft with skylight, and a guest room with a fun egg chair. Enjoy a fully equipped kitchen, wraparound deck, heated floors, and a rustic outdoor shower. Minutes from Cloudland Canyon’s trails and waterfalls, this serene hideaway is perfect for romantic escapes, group adventures, or anyone ready to “live a little.”

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.

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.

Quaint and Peaceful Fairyland Apartment

Enjoy all the beauty of Lookout Mountain from this quiet, cozy, and private garage apartment. The one bedroom, one bathroom apartment is recently constructed and tucked away on a side street in the Fairyland neighborhood. You are within walking distance of Rock City Gardens and Starbucks. Nearby are numerous opportunities to hike or enjoy scenic views of downtown Chattanooga, which is only a short drive away.