Holiday rentals in Hillsboro

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.

Tennessee’s Only Luxury Safari Tent Getaway

Soak in sweeping mountain and valley views from your private hot tub at this remote, luxury safari tent. Unwind on a plush king bed, sip wine beside the glowing fire feature, and bask in unforgettable sunrises and sunsets. Surrounded by nature, peace, and starry skies, this hidden gem is the perfect escape. Just minutes from waterfalls and hiking, it’s glamping at its most magical—serene, stylish, and tucked far away from it all. Reconnect with what matters: nature, stillness, and yourself.

Holliday Hide Away

1200 sq. ft. very rustic converted pole barn. The floors are stained concrete and the walls are rough saw mill hewn poplar boards. Located on 3 acres of beautiful well kept property. It does not border the lake but is surrounded by Tims Ford Lake and less than 5 minute drive to 3 boat docks and launches. Close to restaurants, shopping venues, hiking trails, water falls and golfing. Pool table, cornhole set, board games & cards in cabin. Visit historic Franklin County and surrounding areas.

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 Tree House Cabin

Experience the fun of living among trees in our treehouse mini-lodge feel check out 2 other cabins Patriot's Retreat & Sunrise Mtn Cabin. Our tree house is extremely comfortable, with a view of the Cumberland mountains. Complete with a full kitchen, bathroom, two-loft sleeping and viewing areas. Several major state parks/hiking within a few miles of the cabin. Exceptional star viewing. The cabin has fiber optic WiFi which is not shared. Pet cats are not allowed as we are allergic.

The Coalmont Cabin – Romantic Lakefront Escape

The Coalmont is a 4 acre waterfront retreat on top of the South Cumberland Mountains of Tennessee, between Nashville and Chattanooga. This 460 sq ft "tiny" cabin sleeps up to 4. Amenities abound with boats, hot tub, fishing, zip line, lawn games, large decks for gathering, fire pit, and beautiful scenery. Perfect retreat for couples looking for a romantic getaway, families wanting to unplug and reconnect with quality time, or anyone looking for a quiet place to work remotely.

Grandview Treehouse with Bluff Views!

We offer a location where you can get away to just relax, enjoy the views and fish in our well stocked pond. But if you’re more adventurous, there are local areas for hiking, repelling, atv riding and cave exploring, all within a short driving distance. Some of these include Stone Door State Park, Greeter Falls, Fiery Gizzard trail, The Caverns music venue and cave tours, and Cumberland Caverns. There is also golfing available at 6 locations within an hours drive or less!

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.

Cozy Cabin close to Tims Ford Lake & Jack Daniels

A cozy cabin awaits you located close to Tim's Ford Lake-1/2 mile from Holiday Landing Marina & Blue Gill Restaurant. Lynchburg, home to popular Jack Daniel's Distillery-only 12 miles away; Nashville-90 mins. Made from handcrafted red cedar, you will be met with a woodsy aroma when entering. Special touches can be found throughout including Jacuzzi tub! Truly a unique wooded cottage, equipped to ensure a relaxing getaway. Pet friendly with an additional pet fee.

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!

The Barn @ Dreamcatcher Farm

Make sure to “heart” our listing so you can find us when you are ready to book. Live the farming dream in Middle Tennessee on Dreamcatcher Farm. Our 13 acre farm is home to Nigerian Dwarf goats, Santa Gerturdus cattle, a couple of horses, and the Labs and barn cats that run the operation. Come enjoy some down time in a quiet country setting with friendly farm animals.