Vacation rentals in Hillsboro

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Top-rated vacation rentals in Hillsboro

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Top guest favorite

A cozy sleeping area is shown with a spacious bed covered by a textured blanket. The elevated tent features open mesh windows, offering unobstructed views of the landscape beyond, with natural light illuminating the wooden walls and nearby bedside lamp.

Tent in Altamont

5 out of 5 average rating, 144 reviews

Luxury Safari Tent Near Top Rated Waterfall & Park

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.

Guest favorite

Aerial view of a stunning waterfall cascading over rocky cliffs into a serene pool below. Lush greenery surrounds the scene, providing a natural frame. The image captures a peaceful moment with two individuals seated on a rock, enjoying the tranquil beauty of nature.

Cabin in Morrison

4.93 out of 5 average rating, 270 reviews

Little Mountain Cabin Spectacular Mountain View!

Jaw dropping view from your front porch! PRIVATE, secluded tiny mountain cabin offers solace for your soul. Waterfalls, hiking, ESCAPE the world. 20 mn to State Parks. Awesome slice of heaven tucked on a mountainside. 1,000 acres of wilderness surrounds your cabin w/unobstructed stunning South Cumberland Mountain views. Pristine PRIVATE setting. Mountain sunrises. stars, moonrises. Serenity, peace. Refresh, restore. Charming cabin w/kitchen, loftbed, full bath. Grill, country rockers,heat/ac.

Top guest favorite

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

4.94 out of 5 average rating, 181 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 favorite

A charming house is set in a lush green yard, featuring a covered front porch with two rocking chairs. The exterior is adorned with light-colored siding and wooden shutters, complemented by a well-maintained lawn and trees providing shade.

Home in Morrison

4.98 out of 5 average rating, 158 reviews

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.

Top guest favorite

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, 584 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 favorite

A serene cabin is surrounded by colorful autumn foliage, reflecting beautifully on the calm water. The warm glow from large front windows invites guests to experience the cozy atmosphere inside, while a small dock is visible along the shoreline.

Cabin in Coalmont

4.98 out of 5 average rating, 317 reviews

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.

Top guest favorite

The interior showcases high ceilings with a large clock prominently displayed above a comfortable seating area. Natural light filters through multiple windows, highlighting a cozy living space that opens onto a covered deck featuring a circular seating arrangement around a firepit.

Tiny home in Tracy City

4.99 out of 5 average rating, 285 reviews

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.

Guest favorite

A charming cabin features a wooden exterior with a sloped roof and an upper balcony. The front porch includes seating options, and large windows allow natural light to fill the space. Surrounded by trees, the setting provides a serene connection to nature.

Treehouse in Altamont

4.96 out of 5 average rating, 305 reviews

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!

Top guest favorite

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, 496 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 favorite

An open living and dining area is presented, featuring a wooden dining table with seating for six. A comfortable grey couch and accent chair create a relaxing space. Natural light enters through windows, illuminating the warm wood flooring and modern décor throughout the room.

Home in Decherd

4.99 out of 5 average rating, 112 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/ YouTube TV and streaming tv. Only 3.5 miles off 1-24 exit 127, Pelham, Winchester.

Top guest favorite

A spacious living area features hardwood floors and an open layout connecting the kitchen, living room, and dining space. A large television is positioned on a media console, while stainless steel appliances are visible in the kitchen. Two ceiling fans enhance the airy feel of the room.

Guesthouse in Tullahoma

4.96 out of 5 average rating, 143 reviews

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!

Top guest favorite

A rustic barn is shown beside a wooden fenced area, with a large open field visible in the background. The scene is framed by a tree with green leaves, and a decorative sun motif is positioned on the barn's exterior.

Barn in Tullahoma

4.98 out of 5 average rating, 190 reviews

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.