Holiday houses in Hillsboro

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Top-rated holiday rentals in Hillsboro

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
The Gipson House, established in 1930, features a charming white exterior and welcoming porch. Lush green plants hang by the entryway, while two bicycles are parked on the lawn, reflecting a peaceful rural setting bathed in sunlight.
Cottage in Village of Pelham
4.98 out of 5 average rating, 137 reviews

The Historic Gipson House Caverns Fan fave

135 guests, 135 five star reviews! This is an historic house. Completely remodeled with modern convenances. Book now for 2026 caverns dates ! Top shelf accommodations ?You’ve found them ! See our reviews ! Guests love the Gipson House ! Private home and property ! Caverns 4 miles/10 mins away. Circa 1930, beautifully appointed Gipson House in scenic Pelham Valley between Chattanooga/Nashville, area has world class hiking , also near Sewanee Recognized super host and guest favorite

Top Guest favourite
The exterior of the property features a unique sloped roof with a combination of stone and wood materials. Surrounded by greenery, the entrance is approached via a paved path that leads to a welcoming entrance area. Outdoor seating is visible on the balcony, nestled among the trees.
Home in Manchester
4.95 out of 5 average rating, 256 reviews

Chalet 638 - state park, golf & The Caverns

Short walk to a state park with golfing. This first floor living space has a kitchen, walk-in closet, large wood fireplace, workout equipment, washer/dryer, grill, fire pit and lots of space. Old Stone Fort Archeological Park with multiple hiking trails, fishing, canoeing and a $9 a round golf course are seconds away. Close to I-24 this centrally located Tennessee property gives equal access from Nashville to Chattanooga. Explore parks, vineyards, distilleries and Tennessee history from here.

Top Guest favourite
A modern dome structure stands elevated on wooden stilts amidst lush greenery. The exterior features large geometric windows that reflect the surrounding trees, while warm outdoor lighting strings across the deck, enhancing the peaceful ambiance of the natural setting.
Dome in Smithville
4.98 out of 5 average rating, 126 reviews

Solace Sphere

Welcome to our modern sanctuary nestled in the serene woods of Smithville, just a stones throw away from the tranquil waters of Center Hill Lake. Solace Sphere offers a contemporary twist on the classic dome design, featuring a one bedroom layout with a loft, complemented by a rejuvenating waterfall shower and top-of-the-line appliances for your comfort and convenience. We are located 1-1/2 hours from Nashville and 3 miles from Pate’s Ford Marina Bar and Grill. We hope you find your Solace.

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
A charming cabin with a green metal roof is situated on a grassy hillside. Surrounding trees frame the view, while steps lead from the driveway to the entrance. The cabin overlooks the valley, providing a scenic backdrop of rolling hills in the distance.
Cabin in Altamont
4.97 out of 5 average rating, 621 reviews

Sunrise Mountain Cabin

Welcome to Sunrise Mt. Cabin is located on top of the Cumberland Plateau with a great view of the valley check out our 2 other cabins Patriot's Retreat & Sunrise Mtn Treeshouse. The cabin has approximately 1400 square feet and is fully furnished with full kitchen and more. Hiking trails and fishing pond only a short walk away. Several major state parks with hikes within a few miles of the cabin. The cabin has fiber optic WiFi which is not shared. Pet cats not allowed; we are allergic.

Top Guest favourite
Home in Tracy City
4.99 out of 5 average rating, 155 reviews

Collier House- Nearby to OHV Park & Caverns Venue

Collier House is a 1000 sq ft 2 bedroom, 2 bath home that accommodates 7 guests. We offer luxurious memory foam mattresses and premium bedding, WiFi , and parking to accomodate your ATV. We are happy to make special requests or accommodations. We are centrally located in Coalmont, TN only 5 minutes from the entrance of the OHV off road park. We are located only 15 minutes from the South Cumberland park trailheads and from The Caverns event venue. We are 1 hour away from Chattanooga.

Top Guest favourite
An A-frame cabin is nestled among tall trees, showcasing a modern design with large glass windows. A wooden deck surrounds the entrance, featuring a seating area with chairs and a fire pit. The outdoor area is partially landscaped with natural ground cover.
Cabin in Monteagle
4.96 out of 5 average rating, 160 reviews

Modern Monteagle A-frame with Hot Tub

Welcome to Camp Mae, a Scandinavian inspired A-Frame stay in Monteagle, TN. Minimalist designed yet elegant, offering the perfect escape- minutes from the Fiery Gizzard hiking trail and Monteagle. Relax in the hot tub or gather around the fire pit. For eco-conscious travelers, we provide an electric car charger. Experience seclusion of the mountains while only minutes from world class hiking, local restaurants and shops. This retreat harmonizes luxury with nature in a serene setting.

Top Guest favourite
The cottage exterior displays a charming entrance with a light blue door framed by a wreath. A cozy seating area is present with two chairs and a small table. A wooden fence adds privacy, and flowering plants are planted along the stone pathway.
Cottage in Village of Pelham
5 out of 5 average rating, 558 reviews

The Milk Barn Cottage

Built in the late 1940's as a working milk barn, the Milk Barn Cottage is 800 sq. ft of cozy comfort. The cottage is near the foot of Monteagle Mountain in the beautiful Pelham Valley. We are half-way between Nashville and Chattanooga, about 2 miles off exit 127 on I-24. The Caverns is about an 8 minute drive away. Pelham has quaint restaurants to visit plus all of the natural beauty in our area. We are also just 13 miles from Sewanee and the University of the South.

Top Guest favourite
Cabin in Coalmont
4.98 out of 5 average rating, 374 reviews

The Coalmont Cabin - Romantic Lakefront Escape

A quiet lakeside retreat made for slow mornings and star-filled nights. Wake to coffee on the deck as the fog drifts across the water, geese gather along the shoreline, and the world feels still for just a little longer. Spend your afternoons out on the lake, gliding through lily pads in a moment that feels like a scene from The Notebook. Tucked among the trees with a saltwater spa beneath the stars, The Cabin is where peaceful seclusion meets unforgettable memories.

Top Guest favourite
Home in Decherd
4.99 out of 5 average rating, 140 reviews

"Near Caverns and Sewanee 2-bedro/2-bath w/EV char

2 bedroom, 2 full bathrooms, totally remodeled home with a large fenced back yard and fully equipped modern kitchen. Easy drive less than 7-mi to Sewanee, and just 10-miles/ 10-12 min to The Caverns. The "Farm View" house offers country views with privacy. A serene place to relax, unwind and retreat while enjoying pastures and country views. "EV/Tesla wall charger", Starlink internet w/ streaming tv. Only 3.5 miles off 1-24 exit 127, Pelham, Winchester.

Top Guest favourite
Cabin in Monteagle
5 out of 5 average rating, 163 reviews

The Sundowner

Come find serenity at The Sundowner where the view drops layers of stress, the sunsets connect you with wonder, and the deer, coyotes, owls, and other denizens reconnect you to nature. The kitchen is well stocked. Fiber internet. Grill, firepit, washer/dryer. 20 min to The Caverns & Fiery Gizzard Trl w Foster Falls; 15 min to Perimeter Trl, Sewanee; 5 to Monteagle. 3bd/2ba includes open master in loft. Toxin free.

Guest favourite
A modern treehouse sits elevated among the trees, featuring a large deck with wooden chairs and a hot tub. A grill is positioned on one side, with lush greenery surrounding the structure, providing a sense of privacy and seclusion in a serene environment.
Treehouse in Monteagle
4.85 out of 5 average rating, 675 reviews

Scandinavian Treetop Bliss @ Terralodge

Soar into our Scandinavian treehouse on Monteagle’s "bio-gem"! Luxuriate in king beds, a hot tub, and smokeless firepit. Swim or fish in the shared pond, hike to our cave, or play lawn games. With fiber WiFi, 4K TV, and full kitchen, it’s perfect for work or play. Near Monteagle (7 min), Sewanee (15), The Caverns (25), plus epic hikes and lakes. Chattanooga (45 min), Nashville (90). Book this luxe treetop escape!

Popular amenities for Hillsboro holiday rentals

  1. Airbnb
  2. United States
  3. Tennessee
  4. Coffee County
  5. Hillsboro