Vacation rentals in Hillsboro

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Top-rated vacation rentals in Hillsboro

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Top guest favorite

A warm living area is showcased with rich wooden walls and a plush area rug. A leather sofa is complemented by two patterned chairs, while abstract wall art adds a touch of style. Natural light filters in, enhancing the cozy atmosphere.

Tent in Altamont

5 out of 5 average rating, 124 reviews

Luxury Safari Tent with Hot Tub & Sunset Views

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, 268 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

A treehouse structure is seen illuminated in the evening, showcasing a welcoming ambiance. A black calf stands in the grass near a fenced area, with the surrounding farm landscape and trees forming a serene backdrop.

Farm stay in Morrison

4.96 out of 5 average rating, 243 reviews

Phelps Pharm, I Was Almost A Treehouse

The treehouse you always wanted as child but can enjoy as an adult. I started out next to three trees that had to be removed but you still may feel a treehouse sway if the wind blows the right way. We are a working farm raising beef cattle and offer horseback riding lessons, arena rides and trail rides along with kayaking down our local river in McMinnville. Our guests have the opportunity to experience farm life and assist us in gathering eggs, feeding the cows or helping with the horses.

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, 167 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

The spacious living area features large glass windows that showcase woodland views and allow natural light to fill the space. A mix of modern and cozy furnishings includes a black sofa, orange leather chairs, and a wooden dining table, creating an inviting atmosphere.

Home in Monteagle

4.98 out of 5 average rating, 102 reviews

Stayframe: designer getaway w/ private lake access

Welcome to our custom-built Aframe in the woods just 90 minutes from Nashville. This quiet retreat perched on the Cumberland Plateau gives you access to the hikes and waterfalls the area is known for, while offering an elevated guest experience. Enjoy the soaking tub, gas fireplace, fast wifi, Smart TV, well-appointed kitchen, and bluff views. Sewanee University, Cumberland Caverns, Fiery Gizzard, and Sweetens Cove are all within a short drive. Sorry, no parties, events, or photoshoots.

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, 582 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.

Superhost

A wooden deck overlooks the tranquil lake, framed by trees displaying autumn foliage. A fire pit stands at the center, with flames gently rising. Two cushioned chairs provide seating, enhancing the outdoor space for relaxation and enjoyment of the scenic views.

Home in Manchester

4.9 out of 5 average rating, 397 reviews

Fire Lake Estate *NEW* Hi Speed Internet!

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.

Guest favorite

The tiny home sits nestled by the waterfront, surrounded by trees. A large deck features two lounge chairs and a hot tub, with string lights illuminating the area. A fire pit and seating are positioned near the water, enhancing the serene outdoor environment.

Tiny home in Coalmont

4.98 out of 5 average rating, 106 reviews

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).

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, 488 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, 109 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.

Guest favorite

The exterior of a quaint cottage is presented, featuring a white stone façade and black shutters. Lush greenery, including flowering bushes, surrounds the front yard. A small white trellis adds a decorative touch, while a rocky formation sits in the grassy area, enhancing the inviting curb appeal.

Cottage in Hillsboro

4.87 out of 5 average rating, 305 reviews

Eva’s Country Cottage

Our little cottage is halfway between Nashville and Chattanooga. It is only an hour to either city. The Caverns, Bluegrass Underground, is just 15 minutes away. Bonnaroo is just 7 miles up the road and Jack Daniels Distillery and Lynchburg are only 30-45 minutes away. Large lakes and winding rivers are not far away. A quaint older building that was originally built as a church, it was converted into a home in 1964 and has recently been updated and remodeled.

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, 139 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!