Holiday rentals in Bridgeport

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!

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

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.

Cozy Room near I-75 (Private entrance with Bath)

Cozy room in a family home with private entrance and bathroom attached. Our location facilitates the lodging for people traveling between the northeast and southeast. The house has easy access, just 1 min to high way ( I-75 ) on last exit 353 between Georgia and Tennessee line. Is located just 15 min from downtown Chattanooga, Hamilton mall (8 min), Chattanooga Airport (11 min) and many touristic places. We are a family of 4 including 2 medium dogs. We are pet friendly!

Secluded Country Cabin between city and country

Our Secluded Country Cabin is located just off I-59 and only one exit from the I-24 split near Trenton, GA. We’re conveniently located only 15 minutes from downtown Chattanooga, Cloudland Canyon State Park and Lake Nickajack! You will enjoy the peaceful country atmosphere of this private oasis while surrounded by nature, fresh air, and beauty. You will love the convenience if you’re traveling through, and there’s lots to do if you plan to stay a while.

Our Catty Shack

Oliver and Lacey (the cats) would love to welcome you to Our Catty Shack! ***NOTE: Our Catty Shack comes WITH 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.

Tri-state Corner Cabin with a fire pit, hot tub, &

SUNDAY check in ALLOWED. TRI-STATE CORNER CABIN is located inside Paradise Pointe, gated & on a mountain, tristate corner of AL/TN/GA. HIKING TRAIL to tristate corner. Paradise Pointe has 1 HuGe INDOOR POOL HOUSE with outdoor deck. 19 rentals has access to pool house. Cabin has fireplace, fire pit, hot tub etc. Premises has sand volleyball. Enjoy VIEW from BLUFF & POOL DECKS! Cabin sits behind but between 2 other cabins.

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.

Big Living in the Little House

Trade traffic jams for 2 lane country. Only 10-20 min from downtown. But what we call “going to town” is driving to Flinstone for gas or church. Near Chattanooga, hiking, hang t gliding, 10-20 min to Cloudland Canyon, Rock City, Incline, Sunset Rock, Ruby Falls, TN Aquarium, with Lookout Mtn’s bluffs as backdrop.