Holiday rentals in Hillsboro

Remodeled Cottage with Sunroom

3 Bedroom, two bathroom fully remodeled home with very fast internet, big screen 4k smart TV, a fully outfitted kitchen, and a great sitting room on the back of the house. Features: - High-Speed Internet (1000Mb up/down) - 65" 4K Roku TV - Sun Room - Air Hockey - Sound Machines - Luggage Racks - Ironing board & Iron - Games - Dishwasher - Master Bedroom with Private Bathroom - Full Kitchen - Drip & Keurig Coffee Maker Nearby Attractions: - Bonnaroo (6 Miles) - Old Stone Fort Park (8 miles) - R

The Historic Gipson House Caverns Friendly !

126 guests, 126 five star reviews! This is an historic house. Completely remodeled with modern convenances. Book now for 2026 caverns dates ! Top shelf accommodations ?You’ve found them ! See our reviews ! Guests love the Gipson House ! Private home and property ! Caverns 4 miles/10 mins away. Circa 1930, beautifully appointed Gipson House in scenic Pelham Valley between Chattanooga/Nashville, area has world class hiking , also near Sewanee Recognized super host and guestfavorite

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.

Stayframe: a designer getaway with mountain views

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.

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.

Fiery Gizzard Homeplace & Cottage

A private cottage located close to area restaurants and outdoor activities. Approximately 5 minutes to FIERY GIZZARD trailhead as well as dining in Monteagle and Tracy City. Our cottage has a private courtyard where you can grill, chill, and make a fire! A large custom walk-in shower with great water pressure and endless hot water. A large smart tv with excellent internet. Very comfortable bedding and a nice leather recliner. Snacks and drinks in the refrigerator are complementary.

COUNTRY HAVEN TINY CABIN - 7 MIN WALK TO CAVERNS!

This unique tiny cabin that we have called Country Haven is located in the valley of Pelham, TN on Payne Cove Road. Enjoy a scenic view from the porch, stay cozy by the fire pit, or relax by streaming your favorite series on Netflix, Hulu, or Disney plus! The cabin is a 7 minute walk to the entrance of the Caverns if you're here to enjoy a show or to go on a cave tour. We are 6 miles from I-24 off exit 127. 1 hour to Nashville or Chattanooga and 10 miles to Sewanee or Monteagle.

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.

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.

Bluff House—Breath-Taking View…Quiet…Renovated Lux

Peaceful, Park-Like Setting — Convenient to Waterfalls, Hiking, & THE CAVERNS • Relaxing, Private Getaway • Spacious, Clean Home • 15 min from Sewanee Uni. • Close to Coalmont OHV Park • Spacious/Convenient Amenities • Full Kitchen, Equipped to Cook • Desk/1GB Internet w/WiFi • Firepit & GAS Grill • HUGE Observation Deck • 7-Min. From Interstate • Private Parking; Room for RV/Hauler • Small-Town Friendliness & Eateries Minutes Away • Chatt/Nash Attractions—Short Drives

"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/ streaming tv. Only 3.5 miles off 1-24 exit 127, Pelham, Winchester.

Secluded 50 acres w/ Hot Tub, Fire Pit & Fireplace

- Hot Tub - Hike & Walk Trails - Fireplace - Back yard Firepit - Shoot skeet (upon request) - Watch nature - Corn hole & ping pong - Grill - Back yard hammock - Creek - Unplug and Rest Attractions include: -Chattanooga 1h 20m - Historic Bell Buckle Cafe 20m - Murfreesboro 25m - Nashville 55m - Normandy Lake 25m Murfreesboro provides: - Grocery & shopping centers - Theatres - Bowling - Golf courses - Go carts, mini golf, arcade - Dining and more!l