Vacation rentals in Bridgeport

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Top-rated vacation rentals in Bridgeport

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Guest favorite

Home in South Pittsburg

Red Gate Retreat

Perfect mix of privacy and convenience. Short drive to Google data center, fishing & golfing Two miles from downtown South Pittsburg. 10 min or less drive to Sweetons Cove golf course, fishing at Nickajack lake on the TN river. Local dining and wineries, home to several state parks. We offer Parking for boats and side by sides. Take time to stargaze through trees or rock on the covered porch or step off the patio and grill burgers by the fire pit. Come enjoy seclusion just minutes from town.

4.92 out of 5 average rating, 13 reviews

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

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.

4.98 out of 5 average rating, 331 reviews

Superhost

Home in South Pittsburg

Rainbows End River Lodge

Located just 25 minutes from Chattanooga, this recently renovated 4-bedroom, 2 bath delight sits on 12 acres overlooking the Tennessee River and surrounding mountains. Enjoy eating or lounging on the large deck or you're just a short drive from small town cafes and fine dining. The public boat launch is a short 5-minute drive or fish from the bank just steps from the front door. Other nearby attractions include lakes, shopping, antiquing, state parks, historical attractions, and so much more.

4.82 out of 5 average rating, 72 reviews

Top guest favorite

Cabin in South Pittsburg

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.

5.0 out of 5 average rating, 32 reviews

Guest favorite

The living area is filled with natural light from multiple windows, featuring a combination of a plush sectional sofa and patterned accent chairs. A coffee table sits in the center, with a decorative plant positioned on it. Soft lighting enhances the inviting ambiance.

Home in South Pittsburg

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

4.88 out of 5 average rating, 48 reviews

Top guest favorite

A bright living space features a queen bed with decorative pillows and a gray sofa. A kitchenette with modern appliances is visible, alongside a vibrant wall art piece. Natural light illuminates the polished concrete floor, creating an inviting and comfortable atmosphere.

Apartment in South Pittsburg

No cleaning fee- mid week special price!

Located in the heart of downtown South Pittsburg. It is perfect for travelers seeking a unique Southern experience. This charming space combines modern comforts with small-town charm, making it an ideal getaway for families, couples, or solo adventurers. Walkable to so many of South Pittsburghs faves: 100 Ft to Dixie Freeze 200 Ft to Chenchos Cocina 400 Ft to Spill Coffee House 400 Ft to Stevarinos Italian Eatery 7 min walk to Lodge Cast Iron museum/restaurant 8 min drive to Sweetens Cove

5.0 out of 5 average rating, 73 reviews

Top guest favorite

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

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.

4.99 out of 5 average rating, 159 reviews

Top guest favorite

Home in Bryant

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.

5.0 out of 5 average rating, 29 reviews

Top guest favorite

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

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.

5.0 out of 5 average rating, 36 reviews

Guest favorite

The entrance of the cottage is highlighted by a welcoming porch featuring wooden railings and flower pots. A small garden area is visible, adding greenery. Above the door, decorative signs impart character to the blue exterior.

Cottage in Bridgeport

Our pondarosa

Beautiful Cottage house situated in a quiet and safe place surrounded by trees, across a cow’s pasture, close to rivers, lakes, creeks for fishing and boating, wildlife hunting, 15 mins to Jasper Highlands, ghost hunting at South Pittsburg Old Hosp, Lodge Factory Store, 40 mins to Chattanooga, 30 mins to Scottsboro, 10 mins to Russell Cave Natl museum, Railroad Depot museum, a beautiful place for work and leisure, where your comfort is our pleasure!

4.81 out of 5 average rating, 26 reviews

Top guest favorite

Home in South Pittsburg

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

4.98 out of 5 average rating, 89 reviews

Top 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

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.

4.97 out of 5 average rating, 330 reviews