Vacation rentals with a patio in Madison County

The Waffle House: Historic Full Downtown Apartment

The apartment is called Waffle House because it was the home of Waffle House founder Joe Rogers. The space is a full apartment with kitchen, laundry, living room, bathroom and bedroom with a separate entrance. Located on W Deaderick it’s just a short walk to Restaurants , Farmer's Market, and Hub City Brewing. I am the brewmaster at Hub City Brewing & Rock’n Dough Pizza + Brewery, and my wife works for Hitachi Energy. We live in the downstairs unit so are nearby if there is anything you need.

2 Bedroom Midtown House- The Nest on Swan

Welcome to your cozy 1950s house in the heart of Jackson, TN! This charming two-bedroom, one-bathroom home is tucked away on a peaceful dead-end street, offering the perfect balance of privacy and convenience. Centrally located, you're just minutes from dining, shopping, downtown, and the hospital. Hop on the 45 Bypass to head to northside Jackson, just 3 miles away. Whether you're here to explore the town or simply relax, our comfortable space provides all the essentials for a memorable stay.

Cedar Hill Retreat

Welcome to our newly renovated 2-bedroom, 1-bath Cedar Hill Farmhouse Retreat! Perfectly situated just 5 minutes from charming Downtown Medina, 15 minutes to North Jackson, and 20 minutes to vibrant Midtown. Sleeps 6 in cozy, stylish spaces. Sip your morning coffee on the patio, watch goats and cows graze, listen to songbirds, and unwind by the fire pit under starry skies. Perfect for a weekend escape, family gathering, or local event — soak up peaceful country charm with easy city access.

Little Bird Cottage

This is your unique and tranquil getaway. This artistic apartment is so cozy you will want to never leave. There is something interesting to admire at every turn. Set on 2.5 acres of huge trees it's a a delight to find that it is right in the heart of the midtown Lambuth neighborhood. Less than a 5 minute drive to downtown Jackson for great food, great farmers market, great shopping, and great entertainment! Also, .06 miles to the Jackson Madison Co General Hospital.

Peaceful Sears, Roebuck and Co. Mail Order Home.

Come and stay at a freshly remodeled cozy home built in the 1940’s. The home has two bedrooms with living room with pull out couch, a galley style kitchen, dining room and bathroom with large walk in glass shower and soaker tub. Two Smart 55” TV’s in the home and WiFi access for your work. We are centrally located to Freed Hardeman University and downtown Henderson. Only 20 minutes from Jackson. Follow us @kenzley holdings

The Tinker Retreat

Enjoy all the things Jackson has to offer within minutes of this home. Whether your looking for a good nights rest or a fun family game night, The Tinker Retreat is ready to accommodate. Step inside, leave your troubles at the door and relax in our massage chair or catch a game of foosball while enjoying some freshly popped popcorn. This home offers something for everyone to enjoy!

Sunset Ranch

Make some memories at this unique and family-friendly place. "Sunset Ranch" is a newly remodeled home in Three-way. Come enjoy country living with a view in North Jackson. Bring your friends and family to our spacious home that sleeps 8!

Historic Lambuth Neighborhood Flat

Enjoy a unique stay at this centrally-located historic Lambuth neighborhood apartment. Close to the hospital and vibrant downtown, this apartment boasts lots of light and modern fixtures to make any stay feel like home.

Our Little Tinker 2

The Tinker 2 is unique, spacious, cozy and more importantly close to retail shopping, fast food, restaurants, event centers, about a mile off the interstate and more. 2 spacious bedrooms queen beds and 1 full bath.