Holiday rentals in Hillsboro

Luxury Safari Tent | 15 Mins to Top TN Waterfall

Perched above a quiet valley, this beautifully crafted safari tent offers a private, serene escape with sweeping mountain views. Soak in your hot tub beneath the stars, unwind on a plush king bed, and gather around the cozy fire feature as the sun slips below the hills. Guests rave about the peaceful setting, radiant sunrises and sunsets, and nearby waterfalls and hiking trails. Remote, refined, and surrounded by nature — this is glamping, reimagined. Slow down, unplug, and savor the stillness.

Remodeled Cottage with Sunroom

3 Bedroom, two bathroom fully remodeled home with very fast internet, big screen 4k smart TV, a fully outfitted kitchen, and a great sitting room on the back of the house. Features: - High-Speed Internet (1000Mb up/down) - 65" 4K Roku TV - Sun Room - Air Hockey - Sound Machines - Luggage Racks - Ironing board & Iron - Games - Dishwasher - Master Bedroom with Private Bathroom - Full Kitchen - Drip & Keurig Coffee Maker Nearby Attractions: - Bonnaroo (6 Miles) - Old Stone Fort Park (8 miles) - R

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.

Entire home in Morrison/Viola

Relax with the whole family in a 130 yr old newly renovated home located at the foothills of the Cumberland Plateau, tucked away in the small, quiet town of Viola. Enjoy the small-town feel with close proximity to Bersheba Springs, Fall Creek Falls, Isha Yoga, & South Cumberland State Park. Less than an hr to Jack Daniel's & George Dickel distillery. The home has -2 separate bedrooms, located on the main floor. Loft with trundle. Full bathroom. Washer/dryer. Full kitchen with dining room.

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.

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.

The Coalmont Cove - Romantic Lakefront Escape

The Coalmont is a 4 acre waterfront retreat on top of the South Cumberland Mountains of Tennessee, between Nashville and Chattanooga. The Coalmont Cove is a tiny home that sits in the cove of a private lake. The definition of relaxation with adventure only minutes away, you'll find elevated decor, an inviting outdoor space, and beautiful scenery. The perfect retreat if you’re looking for a romantic getaway or a quiet place to disconnect or work remotely (1 GB fiber optic internet).

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.

"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/ YouTube TV and streaming tv. Only 3.5 miles off 1-24 exit 127, Pelham, Winchester.

Owl’s Nest Treehouse Getaway w/ Hot Tub & Fire Pit

Reconnect with nature at this unforgettable treehouse escape. One of the few treehouse cabins in Tracy City, located on 2 acres of beautiful wooded land. We are less than 1 mile from South Cumberland State Park with access to hiking trails, creeks, and Mountain views. Enjoy the sounds of the woods on our elevated deck, or relax in the private hot tub down below. The newly renovated outdoor space includes a grill, fire pit, pond & hanging egg chairs.

Nanny’s House

Located in a country setting on a quiet road, this fully renovated 1800+ sq ft house comes with a 1 acre yard, screened-in porch, and patio with view of the mountains. Local attractions include The Caverns (9.3 miles), South Cumberland State Park (13 miles), Tim’s Ford Lake (15 miles), Old Stone Fort State Park (20 miles). Located halfway between Nashville and Chattanooga about 2 miles from I-24, exit 127.

Phelps Pharm Bunkhouse

Farm bunkhouse with stall boarding availability for our guests with horses. Our bunkhouse and location is great for individuals/couples and can accommodate a family of 4. Please visit our website at Phelpspharm.farm for more information, our story and pictures. There is a link on the website that will take you back to AirBnB to continue your reservation. Thank You.