Vacation rentals in South Pittsburg

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Top-rated vacation rentals in South Pittsburg

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Top guest favorite

The treehouse exterior is framed by vibrant autumn leaves, showcasing a wooden structure with large windows and ornate details. A wooden walkway leads to a charming entrance, warmly lit by ambient lights that create a welcoming atmosphere at dusk.

Treehouse in Trenton

4.97 out of 5 average rating, 283 reviews

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.

Guest favorite

A rustic log cabin is set within a spacious green yard, surrounded by trees. A gravel path leads to the entrance, with stairs ascending to the front porch. Windows provide views of the natural landscape, reflecting a serene outdoor environment.

Home in South Pittsburg

4.89 out of 5 average rating, 456 reviews

Martin Springs Cabin.

This country cabin is a great base for exploring the nearby South Cumberland Park and surrounding area. Convenient to Sweetons Cove Gulf, The Caverns, Adventure Offroad Park, Sewanee, Monteagle, South Pittsburg/Cornbread Festival, Jasper Highlands. right next to I-24. You can't see any other homes from the cabin and adjacent meadow. Year round creek in the property. Meadow trail. New Hot Tub and all new Tuft & Needle mattresses for 2022! Basic amenities provided. Includes Wi-Fi and DVD player.

Top guest favorite

The spacious living area features large glass windows that showcase woodland views and allow natural light to fill the space. A mix of modern and cozy furnishings includes a black sofa, orange leather chairs, and a wooden dining table, creating an inviting atmosphere.

Home in Monteagle

4.98 out of 5 average rating, 101 reviews

Stayframe: designer getaway w/ private lake access

Welcome to our custom-built Aframe in the woods just 90 minutes from Nashville. This quiet retreat perched on the Cumberland Plateau gives you access to the hikes and waterfalls the area is known for, while offering an elevated guest experience. Enjoy the soaking tub, gas fireplace, fast wifi, Smart TV, well-appointed kitchen, and bluff views. Sewanee University, Cumberland Caverns, Fiery Gizzard, and Sweetens Cove are all within a short drive. Sorry, no parties, events, or photoshoots.

Top guest favorite

The exterior of a modern A-frame home features a sleek black façade and a pointed roof. A welcoming front porch is adorned with a planter, while the driveway provides ample parking space. Scenic mountains are visible in the background under a clear blue sky.

Home in Trenton

5 out of 5 average rating, 101 reviews

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!

Top guest favorite

A spacious deck is viewed at dusk, lined with chairs facing a breathtaking sunset. Eight-foot windows reflect vibrant colors of the sky, while trees outline the horizon, providing a serene setting for relaxation.

Home in Lookout Mountain

4.98 out of 5 average rating, 235 reviews

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

Guest favorite

A serene cabin is surrounded by colorful autumn foliage, reflecting beautifully on the calm water. The warm glow from large front windows invites guests to experience the cozy atmosphere inside, while a small dock is visible along the shoreline.

Cabin in Coalmont

4.98 out of 5 average rating, 299 reviews

The Coalmont Cabin – Romantic Lakefront Escape

The Coalmont is a 4 acre waterfront retreat on top of the South Cumberland Mountains of Tennessee, between Nashville and Chattanooga. This 460 sq ft "tiny" cabin sleeps up to 4. Amenities abound with boats, hot tub, fishing, zip line, lawn games, large decks for gathering, fire pit, and beautiful scenery. Perfect retreat for couples looking for a romantic getaway, families wanting to unplug and reconnect with quality time, or anyone looking for a quiet place to work remotely.

Top guest favorite

An open living space showcases a full kitchen with modern appliances and a dining area. A pool table occupies the center with various seating options around. Natural light filters through the large glass garage door, leading to a cozy sitting area with a sofa and chairs.

Farm stay in Monteagle

4.94 out of 5 average rating, 133 reviews

The Wool Attic at Summer Fields

This farm stay is in half of a renovated garage on our working sheep farm. Enjoy the sheep, livestock guardian dogs, and slower pace, while still being close to area attractions. It has an open downstairs with a full kitchen, bathroom, dining area, pool table, and porch. Sleeping areas, upstairs in the attic, or in our sleeping loft are too short for standing but otherwise cozy for sleeping. Farm workers will be doing chores and interacting with the animals during your stay.

Guest favorite

The exterior of a modern cabin is showcased at sunset, featuring a metal roof and large windows. The structure is surrounded by greenery and dramatic rock formations, with warm lights illuminating the porch area, creating a welcoming ambiance facing the Tennessee River and mountain views.

Home in Chattanooga

4.98 out of 5 average rating, 188 reviews

Our Catty Shack

Oliver and Lacey (the cats) would love to welcome you to Our Catty Shack! ***NOTE: Our Catty Shack comes WITH CATS and WITHOUT TV!*** 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.

Top guest favorite

An inviting living area features wooden flooring and a ceiling with natural wood panels. A comfortable sofa is positioned opposite a vintage cabinet and a TV. Natural light filters through the windows, illuminating the space adorned with artwork and a small table with flowers.

Guesthouse in Rising Fawn

4.98 out of 5 average rating, 168 reviews

Hemlock hideaway

Relax with the whole family at this peaceful place to stay. Country setting, 40 minutes to Chattanooga Tennessee, 10 minutes to Trenton Georgia, 20 minutes to Lafayette Georgia. Three miles to Cloudland Canyon State Park. Thirty seven minutes to Tennessee aquarium. Convenient to Canyon Grill, Cafe 136, Lookout Mountain Pizza 2 miles ( open Thursday through Saturday). Hiking, hand gliding, caving plus other available activities.

Top guest favorite

The image displays a two-story house with a wrap-around porch, featuring multiple seating areas. A small stone pathway leads to the entrance, framed by a landscaped yard with ornamental planters. Lush greenery and a large tree complement the exterior's inviting appearance.

Home in Bryant

4.94 out of 5 average rating, 109 reviews

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!

Top guest favorite

A cozy corner showcases a round wooden table with two black chairs. A small sculpture sits center stage, and a microwave is mounted above a mini-refrigerator. Natural wood paneling lines the walls, and a large window offers a view of the surrounding greenery, enriched by flowing curtains.

Cabin in Chattanooga

4.97 out of 5 average rating, 692 reviews

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.

Guest favorite

The exterior of a modern stone and wood home is set among tall trees. Large windows reflect natural light, while a prominent chimney adds architectural interest. A spacious front porch extends across the length of the house, surrounded by manicured landscaping.

Home in Tracy City

4.97 out of 5 average rating, 97 reviews

Starry Night on Monteagle-Retreat @ Water’s Edge

This luxurious and ritzy tiny home in Water’s Edge provides everything you could ever imagine! Luxurious king-size beds dressed with fine sheets and down bedding  •Fully-equipped modern kitchens with countertop bar Two fire places and out door fire pit 75 inch TV for movie nights . The mountains are calling you to come look at the stars as they melt away your stress.