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Whippoorwill Retreat Treehouse

“Come, Relax, & Write Your Own Story” Whippoorwill Retreat is a romantic, family-friendly treehouse tucked in the treetops just 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 retreat to the Canopy Suite, where a view of the stars awaits. Write your fairytale at Whippoorwill Retreat.

Twin Oaks tiny house at The Retreat at Waters Edge

Nestled among the oak trees on Monteagle mountain with amazing views of the Fiery Gizzard reservoir, Twin Oaks tiny house is the perfect getaway! Explore the outdoors on hiking trails that lead to waterfalls, see concerts and enjoy eateries, and it's all so easy to get to! Lots of glass that brings the outdoors in if you just want to relax. Each season brings its own unique perspective. Twin Oaks is truly a one-of-a-kind experience. Stay one night or stay a month, you'll love your time here!

Elm off Main, new apartment!

Located in the heart of downtown South Pittsburg. It is perfect for travelers seeking a unique Southern experience. This charming space combines modern comforts with small-town charm, making it an ideal getaway for families, couples, or solo adventurers. Walkable to so many of South Pittsburghs faves: 100 Ft to Dixie Freeze 200 Ft to Chenchos Cocina 400 Ft to Spill Coffee House 400 Ft to Stevarinos Italian Eatery 7 min walk to Lodge Cast Iron museum/restaurant 8 min drive to Sweetens Cove

Mountain's Edge

The Appalachian A-Frame, built in 2024, is right where you want to be! A cozy, stylish home overlooking the gorgeous views of the valley. While being just far enough away to enjoy the benefits of a quiet mountainous getaway, you're also 25 minutes from downtown Chattanooga, TN, where there is an abundance of amazing activities to partake in! It features a comfortable living space, stunning view with a double decker porch, hot tub, fire pit, and plenty of peace and quiet to relax and enjoy!

Huckleberry's "Cottage on the Pond"

Huckleberry's Cottage, 2 bedrooms, 2 baths located in a secluded gated setting overlooking our pond. Our cottage guests enjoy sitting on the porch overlooking the beautiful pond, taking a leisurely 1/2 mile walk around our pond or sit on the dock fishing, or just listening to the fountain sounds like a waterfall. We invite you to join us at the pond for some bass and bream fishing, please bring fishing gear and enjoy catch and release fishing at your leisure. Angela and James Superhost

The View

Incredible Mountain View Home only 25 minutes from Chattanooga. A short 7 minute drive up the mountain, Trenton, GA and Interstate 59 close by. TAG, Where TN, AL, and GA come together. A mountainous area dominated by Lookout Mtn., with elevations of 2000 feet. There are over 7,000 caves within an hours drive, including Howard’s Waterfall Cave directly below. Hiking trails with waterfalls abound. Our place is more than just a place to spend the night, it is a destination.

The Milk Barn Cottage

Built in the late 1940's as a working milk barn, the Milk Barn Cottage is 800 sq. ft of cozy comfort. The cottage is near the foot of Monteagle Mountain in the beautiful Pelham Valley. We are half-way between Nashville and Chattanooga, about 2 miles off exit 127 on I-24. The Caverns is about an 8 minute drive away. Pelham has quaint restaurants to visit plus all of the natural beauty in our area. We are also just 13 miles from Sewanee and the University of the South.

Large Historical Alpine House near Chattanooga

Built and titled in 1889, the Alpine House has southern charm and hospitality in spades. For the past 6 years, the Alpine House has seen hundreds of families and couples enjoy her warm beds, beautiful sunsets, and homelike atmosphere. This property has been lovingly cared for by its owner and all those who have made memories here. Please come stay with us and add to the collection of great memories this house holds!

Mountain View Cottage

Five (5) Star Cottage without a 5-star price! Quoted review: "Clean, spacious, comfortable, and well-appointed". "The best Air BnB we've stayed at". Great one-bedroom cottage; short drive to Cloudland Canyon, and Rock City. Ruby Falls is a short 20-minute drive featuring a 40-foot climbing tower with five routes of varying difficulty and 700 feet of rushing zip lines with amazing views of the Tennessee Valley!

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)

The Cloud 9 Rooftop Deck at On The Rocks Tiny Home

Welcome to Cloud 9 at On The Rocks, a unique repurposed cargo container getaway atop Lookout Mountain, Georgia. The Cloud 9 Rooftop Deck is a true place to relax and meditate, therefore there is no access television. There are 2 shared fire pits located at each end of the property. Firewood is provided along with ingredients to make s'mores.

Granny's Guest House

Granny's Guest House is in the scenic Sequatchie Valley on 28 acres bordering the river. It's small to medium pet friendly (max - 2). If you are bringing a pet, please read and agree to the pet guidelines in the expanded listing description. Granny's Guest House Is a welcoming home with 2 bedrooms, 2 full baths.