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.

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.

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.

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.

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).

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.

Log Cabin on 50' Miller's Falls - Eco-Village

Cozy Log Cabin on the bluff about 100 yards from the top of 50-foot Miller's Falls. Disclaimer: Waterfall flow is subject to fluctuations in temperature, seasonal droughts, & rainfall. Most favorable seasons for waterfall flow are fall, winter & early spring". Located in the Village on Sewanee Creek, a sustainable community on Tennessee's Eco-Rich Cumberland Plateau. Hike miles of wooded trails.

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.