Vacation rentals in Hillsboro

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Top-rated vacation rentals in Hillsboro

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Guest favorite

Cabin in Morrison

4.93 out of 5 average rating, 269 reviews

Little Mountain Cabin Extraordinary Secluded View!

Secluded, PRIVATE tiny mountain cabin offers solace for your soul! Altamont, TN. Expansive mountain views from private front porch. ESCAPE the world. 20 mn to State Parks, hike, waterfalls. An awesome slice of heaven tucked on a mountainside. 1,000 acres of wilderness surrounds your cabin with stunning South Cumberland Mountain views. Pristine PRIVATE setting. Mountain sunrises. stars, moonrises. Serenity, peace. Refresh, restore. Charming cabin w/kitchen, loftbed, full bath. Firepit, heat/ac.

Top guest favorite

Home in Manchester

4.94 out of 5 average rating, 156 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 modern kitchen area is seen, featuring white cabinetry and stainless steel appliances. A black refrigerator stands juxtaposed with an oven and a hood above. Counter space is utilized for food prep, with utensils neatly arranged. Open shelves showcase kitchen essentials, and a dining area is subtly visible.

Home in Decherd

4.99 out of 5 average rating, 106 reviews

Near Caverns & Sewanee 2-bed/2-bath w/EV charger

2 bedroom, 2 full bathrooms, totally remodeled home with a large fenced back yard and fully equipped kitchen. 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. Easy drive less than 7-mi to University of the South, and just 10-miles/ 10-12 min to The Caverns Concert Hall.

Top guest favorite

Cabin in Altamont

4.97 out of 5 average rating, 580 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

An outdoor deck features a metal table surrounded by four matching chairs. Sunlight filters through the trees, illuminating the lush greenery beyond. A railing surrounds the deck, providing a sense of openness while offering a vantage point of the peaceful landscape.

Home in Tracy City

4.99 out of 5 average rating, 112 reviews

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.

Top guest favorite

A fire feature is displayed atop a sleek table, with flames gently flickering. The background reveals a stunning view of the landscape at dusk, bathed in soft sunset hues as trees frame the scene. The serene atmosphere invites relaxation and contemplation.

Tent in Altamont

5 out of 5 average rating, 109 reviews

Luxury Tent • Mountain Views • Private Hot Tub

Perched above a quiet valley, this beautifully crafted safari tent offers a private, serene escape with stunning mountain views. Relax in your hot tub under the stars, stretch out on a king bed, and gather around the cozy fire feature as the sun dips behind the hills. Guests love the peaceful setting, vivid sunrises and sunsets, and nearby hiking trails and waterfalls. Remote, refined, and surrounded by nature—this is glamping reimagined. Slow down, unplug, and savor the stillness.

Guest favorite

The exterior of a charming cottage is framed by towering trees and lush greenery. A small boat rests on a gravel path beside the house, inviting exploration of nearby water features. The entrance is accentuated by a welcoming porch that enhances the natural surroundings.

Tiny home in Tracy City

4.98 out of 5 average rating, 184 reviews

2BR Nature Getaway in Tiny Home w/ Lake access

Nature's Nook is a charming two-bedroom cottage. Combining nature with cutting-edge design draws inspiration from all over. Providing a fairytale experience with a cozy interior amidst towering trees. Nature's Nook embraces the beauty of nature with the inside scent of a campfire-lit night to birds singing good morning. This provides the ideal getaway to relax but still includes hiking and adventure. Nature is calling you at the Nook. . . Follow us on our socials @NaturesNookTN

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, 295 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.

Guest favorite

A wooden picnic table with attached benches is placed on a deck overlooking a grassy area and distant hills. A solitary tree stands in the background, surrounded by lush greenery and soft clouds in the sky.

Treehouse in Altamont

4.97 out of 5 average rating, 292 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

Cottage in Village of Pelham

5 out of 5 average rating, 482 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.

Guest favorite

Home in Chattanooga

4.98 out of 5 average rating, 184 reviews

Our Catty Shack

Oliver and Lacey (the cats) would love to welcome you to Our Catty Shack! ***NOTE: Our Catty Shack comes WITH CATS and WITHOUT TV!*** This spiritual retreat is nestled between imposing ridgelines, abuts a state forest, and faces the powerful Tennessee river. Enjoy dramatic sun and moon rises. Luxuriate in the hot tub. Feast your eyes on the views. Only 15 minutes to downtown Chattanooga - with the peace of the country - have it all here.

Top guest favorite

A cascading waterfall flows down a rocky cliff, surrounded by lush greenery. Sunlight filters through trees above, creating a serene atmosphere. Waters pool at the base, reflecting the natural surroundings and inviting peaceful contemplation by the rocky shoreline.

Barn in Tullahoma

4.98 out of 5 average rating, 179 reviews

The Barn @ Dreamcatcher Farm

Make sure to “heart” our listing so you can find us when you are ready to book. Did someone say baby goats?!?! 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.