Vacation rentals in Whiteside

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.

Tiny Home with Big Outdoor Space

Our tiny home is a cute, cozy guest house located just 15 minutes from downtown Chattanooga! It sits on a large property alongside your host’s home. Come enjoy the fresh air, play some yard games, sit by the fire, or relax on the hammock! If you’re traveling with your pet, we have a fenced in area for when they get the zoomies. We are conveniently located right off I-59 and within 15 minutes of Lookout Mountain, Cloudland Canyon State Park, Nickajack Lake and the hanggliding Flight Park!

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.

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.

Mountain's Edge

Mountain's Edge by AAF, 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!

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.

NEW Waterfront-Dock-Kayaks-SUPS- TN River Gorge!

20 MINUTES to DOWNTOWN!! One bdrm APARTMENT, Mountain Modern style, Water Front, located in the heart of the scenic Tennessee River Gorge! Built in 2023, our residence was designed to accommodate guests in a completely separate apartment with all of the amenities and spectacular views of the TN River Gorge. We'd love for you to share all of our outdoor areas with us for fun and relaxing days on the water with kayaks, paddle boards, boat dock, outdoor dining area & fire pit!

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.

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!

Nickajack Overlook

Please note - this rental is not on the lake and does not have lake access, it just overlooks it from across the road. There are three boat launch access areas that are 6 minutes from the property. This cottage overlooks Nickajack lake and is a perfect place to relax! Located outside of Chattanooga, just one mile off exit 161 on I-24. This location has 2 king beds, and a small bunk room (with RV size mattresses)

Scandinavian Treetop Bliss @ Terralodge

Soar into our Scandinavian treehouse on Monteagle’s "bio-gem"! Luxuriate in king beds, a hot tub, and smokeless firepit. Swim or fish in the shared pond, hike to our cave, or play lawn games. With fiber WiFi, 4K TV, and full kitchen, it’s perfect for work or play. Near Monteagle (7 min), Sewanee (15), The Caverns (25), plus epic hikes and lakes. Chattanooga (45 min), Nashville (90). Book this luxe treetop escape!

Glenn Falls Tiny Cabin

Get the best of both worlds! Drive 4 miles to downtown Chattanooga to enjoy some of the best restaurants, art and music in the south, and then retreat to our one-room, tiny cabin on a private two acre wooded lot on the side of Lookout Mountain. Walk out the front door and onto Glenn Falls trail and explore the year-round majesty of Lookout Mountain. 10 minutes from Rock City and Ruby Falls.