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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.

Silver Oaks

Silver Oaks is a perfect spot to share a weekend getaway for two or gather a friend group of four. Overlooking the Tennessee River, you can take a nap on the hammock, play lawn games in the open backyard or relax on the porch while enjoying dinner and a glass of vino. Enjoy an incredible view overlooking the bluff and don't forget your swim trunks if you want to take a dip in the pool. This quiet property allows you to unwind, refresh and slow down a notch from the fast paced work week routine.

Cloudland Canyon Cozy Private Hideaway

Meet Little Nelly! A cozy mountain escape for 2 guests max. This tiny charmer (under 200 sq ft) sits atop Lookout Mountain with quick access to hiking, biking, waterfalls, caves, fishing & even hang gliding! Cloudland Canyon is 5 min away—a breathtaking park with stunning trails. Chattanooga & Ruby Falls (30 min) and McLemore Resort (15 min) offer great bites, drinks & epic mountain views. Includes a mini fridge (no freezer), microwave, and coffee, cream & sugar. Little Nelly’s got you covered!

Mountainfarms' Farmhouse -pet friendly, near Chatt

Come enjoy country life in our Civil War era, newly renovated farmhouse. Located on 19 acres in a beautiful setting at the foot of Lookout Mt. There are 2 springs to dip your feet in, woods to hike in, a rocking chair front porch & a large entertaining back porch with great views of the mountains, woods, old outbuildings & beautiful pastures. Inside, modern amenities along with several original architectural elements. Restaurants, many attractions, outdoor activities & Chatt within 30 min.

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 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

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.

Fannie's Place

This tiny home is on the historic home site of Fannie Mennen and the Plum Nelly Clothesline Art Show. She even named the road. The home is brand new, artfully decorated and has 1 double bed, 1 bath, a sleeping loft with 2 twin beds, and a queen sleeper sofa. The view is from 2000 ft elevation and looks into the valley and across to the mountain again. There is civil war history on the property. There is a 100 ft drop so guests are asked to not stay here with young children.

Canyon Cabin with Carport and WiFi, Dog-baby ok

Built in ‘16, this lovely little cabin in a little cabin neighborhood is cozy and convenient. Near Cloudland Canyon State Park (1.5m), Hanggliding (8m), Chattanooga (28m), Canyon Grill restaurant (.6m), and many wedding venues. Queen bed in main level bedroom, full bed in open loft and twin pull-out in the living room. Private screened back porch, slackline, WiFi, TV, Gas grill, carport. Max 2 dogs are ok. No dishwasher, ice-maker or fire pit. NO SMOKING or tow-behinds.

Adorable Lakeside Lookout Cabin - Water/Mtn Views

Our adorable lakefront cabin with breathtaking views of Lookout Mountain and Johnson Lake. Enjoy swimming, kayaking, hiking, caving, fishing — right in your backyard! Inside you'll find a full kitchen, full bathroom, queen bed + sofa bed and cot too. Plus, pet-friendly! Must-Dos: - Cloudland Canyon (15 min away) - Wilderness Outdoor Movie Theater (15 min) - Lookout Hang Gliding (20 min ) - Downtown Chattanooga (20 min) - Ruby Falls (25 min) Book today!

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!