Holiday rentals in Lookout Mountain

Ray's Place on Lookout Mountain

From the back deck you can see 3 states! Gigabit speed wifi is 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 und

Lookout Mountain Bluff Hideaway with views

Arbnb Management only allows listings as "Whole House" or "Shared". This arbnb is a completely separate floor (with its own separate entrance) that is not by definition "shared". So as to alleviate any confusion: This arbnb is the lower level/floor of this house. The owner lives upstairs and will never come downstairs unless requested by the guest. Please read the aforementioned prior to booking so that there is absolutely no confusion regarding the listing as 'Whole/Entire House'.

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

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.

Scenic 2-bedroom cabin with heavenly views

This custom built 2 story, 2 bedroom, 2.5 bath home right on the bluff of Lookout Mountain offers majestic views, peaceful and calming scenery, and the chance to feel like you are right at home. Our goal is to provide what we would want in a vacation home for your family and more. Relax and unwind on the balcony with a cup of coffee, or on the patio with a glass of wine with dinner, or right by the fire pit at night as you watch the sunset. Come and enjoy a slice of heaven.

The Cabin at Wayside for a cozy, woodsy getaway!

Located atop the forested landscape of Lookout Mountain, but just a 10-minute drive from Chattanooga, the Cabin at Wayside offers privacy and quiet in what is described as a luxury tree house. It's located high up in Wayside Estate and surrounded by miles of biking and hiking trails. The cathedral ceiling and windows create a cozy living, dining and cooking area. A main floor bedroom and sleeping loft make the cabin perfect for couples, friends and small families. 

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.

Riverfront Getaway with a View

Featured on Outside Online: “The 12 Coziest Mountain-Town Airbnbs in the U.S.” Nestled in the Tennessee River Gorge, this cozy cabin offers stunning views, river access, and peaceful seclusion—just minutes from Downtown Chattanooga. Whether you're sipping coffee on the porch, fishing at sunrise, or hitting a nearby trail, it's the perfect blend of nature and city adventure in America's first National Park City.

Cloudland Cottage

This cozy getaway blends into Lookout Mountain and emphasizes the beauty of the land inside and out. Every room draws natural light and calm. Convenient drive to all of Chattanooga's natural wonders, a short distance from charming Lookout Mountain town life and St. Elmo neighborhood. Our good friend Sarah and her pup Timber live in a separate apartment downstairs, and tend the garden during the season.