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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.

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.

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.

Wooded Writer's Retreat with Pool

Book NOW for family pool fun get-away. A peaceful health-conscious 3-bedroom tri-level at the ft. of Lookout Mtn. 2 fireplaces. Upper 2 levels are yours exclusively. Lower level office not accessible. Advanced air purification system. Bottled water NOT needed with reverse osmosis filter. Ideal for families, small retreats, or parents of students. Covenant College is visible from the kitchen & attractions minutes away. Plan ahead for Spring-Summer. Open pool season. No pets allowed.

Old Blue Chair TinyHouse: Lookout Mtn Sunset Views

CNN and HGTV-featured tiny house with the best sunset view on Lookout Mountain. Old Blue Chair sits at the cliffside with a Dutch door overlooking the valley 1,400 feet below. 10 minutes from Cloudland Canyon, Rock City, and Ruby Falls; scenic drive to downtown Chattanooga. Sleeps 5 with a queen + twinxl + sofa bed, Potter-esque reading nook, and multiple lofts. Family-friendly. Extra-spacious kitchen and bath by tiny-house standards. Self check-in, free parking, sundeck, and fire pit area.

Barndominium | Views of Lookout Mtn | NEW hot tub!

Welcome to the Barn on Hemlock Hill! Located in Chatt Valley just south of Downtown Chattanooga in the beautiful countryside of North Georgia. Includes a NEWLY added 4 person hot tub! The Barn offers views of Lookout Mtn and is a great place to rest, relax, and enjoy the 4 acres the property sits on. This home is a 15 minute drive from the adorable town of Saint Elmo and several nearby attractions like Ruby Falls, the Incline Railway, and Rock City. We would love to host you!

Peaceful Historic Maple Cottage near Lookout MTN

Enjoy the relaxing space of this remodeled historic home built in 1910. Located only 6 miles from downtown Chattanooga, and just minutes to popular hot spots such as Rock City and Ruby Falls, this is the perfect place to call home for a staycation or vacation. Make some memories at this unique and family-friendly one bedroom cottage in the "country" that is also SO close to the city. Guests here will also enjoy fresh local eggs during their stay(when in laying season!)

Terrace - Stunning Views Floating among the Trees

A quick hike down the wooded trail reveals our modern home reaching out above the slopes of Lookout Mountain. Simple architectural lines guide the eye out, while sleek and calm interior allows the the mountainside environment to take center stage. Breath deep, spend time with folks you love and settle in. NOTE! The trail is built with sections of native stone and logs, so guests with mobility issues may find the walk to and from the parking pad challenging.

1921 Chattanooga Valley The Little Blue Farmhouse

Step back in time and make memories at this cozy 1921 farmhouse! Nestled at the foothills of Lookout Mountain, this family-friendly retreat offers privacy and charm while being just 15–20 minutes from Chattanooga, Chickamauga Battlefield, and Cloudland Canyon. Enjoy evenings by the firepit, relax in the peaceful countryside, and explore all the area has to offer. 3 bedrooms, 2 baths, and all the comforts of home await. Book your stay today! 🏡🌻🐓

Natsukashii Haus -Ghibli tribute

In Japanese Natsukashii means something akin to nostalgia, like a fond childhood memory. And for many of us, the Ghibli films that inspired this space are the embodiment of that feeling. From the moment you step through the door of this one of a kind space, you'll feel the love our artists put into it! Sleep in Howl’s bedroom or Totoro’s nook and relax in our authentic Japanese soaking tub! Come stay and let us spirit you away!

Chatt Vistas Oasis|3bdrm|5mtoTN|PoolDeckBBQFirePit

Welcome to your charming country retreat! This fully furnished home offers a cozy and relaxing atmosphere with its inviting pool, fire-pit area, and a spacious, fully fenced backyard. Centrally located just 4-6 minutes from TN/St. Elmo and Lookout Mountain, it's perfect for exploring Chattanooga. The home features 3 bedrooms and 1 bathroom. Enjoy your peaceful getaway in this delightful and convenient destination!

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)