Vacation rentals in Hillsboro

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Top-rated vacation rentals in Hillsboro

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Top guest favorite

A rustic loft building is shown with a wooden exterior and metal roof. A spacious porch is featured, equipped with seating, a charcoal grill, and string lights. Steps lead up to the entrance, surrounded by lush greenery, providing a tranquil woodland setting.

Guesthouse in Spencer

4.92 out of 5 average rating, 335 reviews

Hannsz Hideaway

Welcome, I have just over 20 acres of land, mostly wooded. This has now become an active family farm that requires land and livestock maintenance on a daily, you may hear a bit of noise during daylight hours, unless it’s a holiday weekend when my kids visit, those weekends can get a lot louder. I have been trying to keep my kids quiet for nearly 38 years…..if you’re a parent, you understand. Ha. It’s beautiful here, and your comfort is top priority. Beautiful sunsets and the sounds of nature.

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, 183 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 spacious king bed is featured in the foreground, adorned with neutral-toned linens. The tent's large mesh window showcases expansive views of rolling hills and a serene sky, creating a connection to the surrounding nature.

Tent in Altamont

4.99 out of 5 average rating, 120 reviews

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.

Guest favorite

A welcoming porch area features vibrant red flooring, complemented by a metal table and chairs. A vintage mailbox stands prominently, while a grill and a chiminea add to the rustic charm. Potted plants are placed nearby, enhancing the outdoor living space.

Cabin in Estill Springs

4.95 out of 5 average rating, 276 reviews

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.

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, 161 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 treehouse-style cabin stands elevated on stilts, surrounded by lush greenery. A spacious deck is visible at the front, offering an outdoor seating area. The roof has a distinct metal finish, enhancing the cabin's secluded nature. Trees provide natural shade around the structure.

Cabin in Altamont

4.97 out of 5 average rating, 328 reviews

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.

Top 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, 121 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).

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

A quaint cabin is set against a lush backdrop of trees, featuring a welcoming front porch with steps leading up. Colorful flowers bloom in the foreground, adding vibrancy to the scene. The surrounding area is peaceful, with ample natural space visible.

Cabin in Tracy City

4.91 out of 5 average rating, 117 reviews

Cozy Cabin

Early check in available on Fridays...just ask! This cabin for 2 is located on 2+ acres of forest in the mountains. Endless hiking trails in the area... Grundy Lakes just down the hill... This 250 sf tiny home has a kitchenette ( sink, microwave and mini fridge) a dining table and dble bed, in one large room. The bathroom includes a shower, toilet. Includes wifi access and a patio. (check-in/ out times are in CST) The Caverns are close by! NO service animals. sorry.

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 Pelham

5 out of 5 average rating, 500 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, 115 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, 146 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!