Holiday rentals in Madison County

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.

The Waffle House: Historic Full Downtown Apartment

We call this space the Waffle House because it’s the historic home of Waffle House founder Joe Rogers. The space is a full apartment with kitchen, laundry, living room, bathroom and bedroom. The apartment is located on W Deaderick and is just a short walk to Jackson Walk Restaurants , Farmer's Market, and Hub City Brewing Taproom. I am the brewmaster at the local brewery, and my fiancé works as a reporter for the local newspaper. We live downstairs with our two dogs, Layla and Morri.

Cozy studio apartment

Welcome to our recently renovated, studio apartment, just steps away from "The Walk," or a short drive to "The Columns." Perfect for solo travelers or couples seeking a cozy retreat, our modern apartment offers a blend of comfort and convenience. As you step inside, you'll be greeted by the warmth of our inviting fireplace, creating a cozy ambiance for relaxing evenings. Experience the perfect blend of comfort and convenience at our apartment. Book now for your next getaway!

Charming 3 Bedroom House Minutes from Downtown

Centrally located on Highland Ave., this three bedroom home is minutes from Jackson's quaint Downtown, the Carl Perkins Civic Center, The Ned, Jackson Madison County General Hospital, the Jackson mall and much more. Jackson, the Hub City and birthplace of Rockabilly, is a wonderful base from which to explore West Tennessee and Northern Mississippi, including Shilo, Parker's Crossroad, the Loretta Lynn Ranch, Tennessee Safari and so much more.

Swan House

This two bedroom, newly renovated 1950’s home exhibits historic midtown charm paired with modern style. Our quiet, dead-end street offers the space to get away, while being conveniently located ½ a mile from the Hospital and right around the corner from the local shops and restaurants of downtown Jackson. Two minutes from the bypass for a quick drive up north; ten minutes from Union University.

Tiny treehouse

The tiny treehouse is located on a family family. There is a lake for fishing. It is a short hike from the property through open trails. Bring your fishing poles and tackle for a fun trip on the lake. Sit by the fire pit and have s'mores and enjoy the peace and serenity of the outdoors. This is a quiet , private place to get away from the noise and rush of the city.

The Johnny Cash Apartment in Casey Jones Village

This 2nd floor apartment is moments from I 40 and right next to Casey Jones Historical train depot. Casey Jones Village offers a museum, ice cream parlor, restaurant(Old Country Store), an art gallery, and so much more! Home of the Dixie Cafe and tons of beautiful things to see! Any season the Casey Jones Village is a wonderful place to see!

Welcome to The Lily Pad!

Keep it simple at this peaceful and centrally-located place. Located just minutes from downtown Jackson, Jackson Madison County General Hospital, The Lift, The Ballpark at Jackson, shopping and restaurants, The Lily Pad is ready for your overnight stop, weekend getaway, work trip or extended stay.

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!