Vacation rentals in Bridgeport

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.

Window Rock | Jackson Point · Modern Bluff Retreat

A design-led retreat on 7 private acres above the valley. Two bedrooms, 2.5 baths, panoramic views. Near Sewanee on Tennessee's Cumberland Plateau — close to MICHELIN-recognized dining, world-class hiking, and some of the darkest skies in the Southeast. Soak in the cedar tub. Put a record on the vinyl station. Sit on the deck at sunset and forget to check your phone. See more images and videos on our socials: @windowrockmodern and don't forget to check out our sister property, The A-Frame.

The Estate - Luxury with Pool Table & Game Room

Welcome to the Estate, a fully renovated mid-century 3-bedroom ranch home amongst the trees on peaceful South Pittsburg Mountain. Enjoy a relaxing atmosphere with mountain views, 5-star chef's kitchen, pool, gaming, and more in this luxury home. This is for the Main House only. In proximity, the separate "loft" sleeps 6 and is available in our other listing! ⬥ Only 10 minutes from Sweetens Cove Golf Club ⬥ 30 miles to downtown Chattanooga ⬥ 25 miles to Sewanee, The University of the South

Waterfront•Hot Tub•Arcade•Sweetens Cove Lodge

Located 2 min from Sweetens Cove Golf Club, this luxurious property is the perfect golfer’s getaway & nature retreat all in one. Unwind in the private hot tub or gather around the outdoor fireplace on the spacious patio. Nestled along a large scenic creek, guests have direct access to water activities making it an ideal nature getaway for outdoorsmen/families to escape city life. With high-end amenities and a tranquil setting, this property offers the perfect blend of relaxation & adventure.

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.

Unique mountaintop farm cabin w/outdoor pavilion

This unique, 3 story, secluded cabin is located on a mountaintop farm w/hiking trails. Perfect for adults who want to hike; hunt/fish; experience farm living; or just enjoy a quiet get-away. High speed WiFi and an outdoor pavilion & fireplace. Free early check-in and late check-out when available. Although remote, it's 15 minutes to Walmart & restaurants & 45 minutes to Chattanooga. Because introducing strange animals is unpredictable, we ask that you respect the no pet policy.

The Perch

The Perch by AAF, built in 2026, 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.

Cozy Getaway with a View!

Property includes 3 bedrooms, bathroom with tub/shower combo, living room with TV, office/desk space, dining area that seats 6, kitchen, and laundry room. The back porch has a patio set that seats 6, making it easy to enjoy the beautiful view! The patio also includes a grill. The back patio/yard also has a hot tub as well as a firepit that is perfect for those relaxing, romantic evenings! The city lights in the valley are mesmerizing at night!

Cast Iron Cabin - Secluded Mountain View & Hot Tub

Cast Iron Cabin is a very private, adults-only (18 and over) rental cabin located on South Pittsburg Mountain. Primarily focused on couples & golf trips and a vacation rental when our family is not using it. Situated on 10 acres of heavily wooded land and offers fantastic views of the Tennessee River from the hot tub! You are only: 10 Mins to Lodge Museum of Cast Iron 15 Mins to Colonial Chemical 20 Mins to Sewanee 35 Mins to Chattanooga

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.

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)