Holiday houses 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.

Secluded Luxe Tent | Stargaze from Your Hot Tub

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.

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.

Fire Lake Estate-*Views *Hot Tub* *GAME ROOM* WiFi

All fresh, new and ready for guests, this completely renovated lake home with gorgeous water and sunset views will amaze you and leave you breathless as you watch the famous Fire Lake sunset from almost every room in the house. Located conveniently just minutes off interstate I-24, centered 1 hr from Nashville and 1 hr from Chattanooga and Only 8 miles from Bonnaroo Music festival. Bring your boat or kayak as the small neighborhood is located right next to a boat ramp and swimming area.

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.

Cozy tiny home ☆Sleeps 4 w/ great outdoor space

Relax & unwind at our tiny home located in Tracy City Sleeps 4-Queen bed in private bedroom & upstairs loft Covered deck w/ gas firepit Campfire in backyard Electric fireplace inside Outdoor obstacle course for kids Fully stocked kitchen 3 Tv's, DVD players & DVD's Fishing poles Great restaurants and shops Bike and hiking trails nearby Kayak & canoe rentals Gas grill 90 min from Nashville, 45 min from Chattanooga, & 15 min from the University of the South in Sewanee.

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.

Woodland Ct. Cottage

This one bedroom guesthouse is the perfect stay for you and your loved ones! Conveniently located in the heart of Tullahoma! Within walking distance of just about everything you need from grocery stores, restaurants, local coffee shops, and more! We are located just 20min from the famous Jack Daniels Distillery and 15 min from George Dickle! If you are interested in some nearby hiking be sure and check out Short Springs and Rutledge falls!