Holiday houses in Bridgeport

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Top-rated holiday rentals in Bridgeport

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Top Guest favourite
A gathering area features several red Adirondack chairs arranged around a central fire pit. The cottage is visible in the background, set among trees, with a view of the lake just beyond, enhancing the outdoor space for relaxation.
Cottage in Hollywood
5 out of 5 average rating, 39 reviews

Long term stays for extended work or families

Designed specifically for extended work/family stays. This spacious home offers comfort, privacy, and functionality for professionals working near Scottsboro or family extended stays. Desk work area, 2 bdr 2 bath w/2 queen beds in each room making it spacious for families. Beautiful farm view from a covered side porch. Water view from the back deck with gas fire pit. 10 miles from Scottsboro with easy access to Hwy 72. The home is ideal for longer stays without the hassle of apartment living.

Top Guest favourite
A spiral staircase leads to the upper level of a rustic cabin living space. A stone fireplace with a large clock is centrally positioned. Rich wood beams and paneling complement the cozy seating area, which includes a sofa, enhancing the warm atmosphere.
Cabin in Bridgeport
5 out of 5 average rating, 31 reviews

Unique mountaintop farm cabin w/outdoor pavilion

This unique, 3 story, 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 available for your convenience. 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.

Top Guest favourite
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, 318 reviews

Whippoorwill Retreat Treehouse

“Come, 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.

Top Guest favourite
The zome structure features a unique geometric design with large, faceted glass panels that reflect the surrounding greenery. Steps lead up to a wooden deck, with a wooden storage area for firewood visible near the entrance. Nature envelops the home, enhancing its secluded setting.
Dome in Rising Fawn
4.99 out of 5 average rating, 140 reviews

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.

Top Guest favourite
Home in Bryant
5 out of 5 average rating, 23 reviews

Grandpa’s Farmhouse at Price Pond

Rooted in Faith , Restored with Love. Relax and unwind in this country farmhouse surrounded with maples , dogwoods , chestnuts and many more among the picturesque setting. Gather with your family in the spacious family room and kitchen. We have a large game room for families to enjoy. Have quiet time in our library filled with lots of vintage and new books. If you want to enjoy the outdoors we have a pond for fishing. Visit our farmhouse where family roots run deep and hearts find rest.

Superhost
Cabin in Trenton
5 out of 5 average rating, 4 reviews

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!

Guest favourite
A yurt stands on a spacious deck, surrounded by trees and breathtaking mountain views. The structure features a rounded top with a domed skylight, and the clear sky enhances the natural scenery in the background.
Yurt in Rising Fawn
4.96 out of 5 average rating, 850 reviews

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.

Guest favourite
Home in Trenton
4.96 out of 5 average rating, 151 reviews

The View

Incredible Mountain View Home only 25 minutes from Chattanooga. A short 7 minute drive up the mountain, Trenton, GA and Interstate 59 close by. TAG, Where TN, AL, and GA come together. A mountainous area dominated by Lookout Mtn., with elevations of 2000 feet. There are over 7,000 caves within an hours drive, including Howard’s Waterfall Cave directly below. Hiking trails with waterfalls abound. Our place is more than just a place to spend the night, it is a destination.

Guest favourite
Cabin in Sewanee
5 out of 5 average rating, 14 reviews

Secluded A-Frame Cabin w/ Sunset Mountain Views

Welcome to Heeler’s Ridge, a cozy A-frame perched along the ridgeline. Surrounded by hardwoods and valley views, it’s made for slow mornings and starry nights. Enjoy warm wood interiors, vaulted ceilings, and sun-lit glass walls that bring the treetops inside. Sip coffee on the deck, watch sunrise from bed, and unwind with books or board games. The open loft layout and thoughtful touches make it ideal for couples, solo retreats, and creative escapes.

Top Guest favourite
Home in South Pittsburg
4.99 out of 5 average rating, 77 reviews

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

Top Guest favourite
Cabin in South Pittsburg
5 out of 5 average rating, 16 reviews

Window Rock | Jackson Point · Modern Bluff Retreat

A design-led retreat on seven 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 social media: @windowrockmodern.

Top Guest favourite
A spacious living area features a large sectional couch and a wooden coffee table with two cups. Natural light fills the room through wide windows, and a mounted television displays a scenic landscape. A stone wall adds texture and warmth to the space.
Home in Guild
4.95 out of 5 average rating, 117 reviews

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)

Popular amenities for Bridgeport holiday rentals

  1. Airbnb
  2. United States
  3. Alabama
  4. Jackson County
  5. Bridgeport