Vacation rentals 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.

Studio Apt on 5th

The Studio on 5th in Henderson, TN is close to Freed-Hardeman University (3/4 mile) & 25 min. from Jackson. This studio w/ 1 queen size bed, 1 bath & kitchenette guesthouse is good for couples & solo adventurers. It is located in a quiet neighborhood next to the host's family home. Includes: Off-street parking, complementary coffee & snacks, Wi-Fi, soaps, shampoo, fresh towels & linens, & outdoor seating. **Simple Check in & Check Out! No "to do" lists!** **Super hosts for over 6 years!**

Pearl Cottage in Casey Jones Village

Step back to a gentler time in this pre-civil war shotgun house in the historic Casey Jones Village. A perfect getaway spot for couples for their honeymoon or anniversary or people wanting to get away for a spiritual retreat. Pearl House is complete with a claw foot tub, a huge shower and his and her robes. There are some wonderful books to read at Pearl, many about history and a great collection of cookbooks. It features a complete kitchen, washer and dryer; all the modern amenities.

Daisey's Homeplace

We hope you enjoy this restful, comfy 3 bedroom/2bath home filled with beautiful antiques along with all the amenities you need. It has 4 smart TVs, fenced in back yard with private patio to sit, covered parking, and board games for the whole family. It is located in North Jackson with many restaurants and shopping centers nearby. Daisey’s Homeplace is in honor of where we found and rescued our second dog, Daisey, who desperately needed a family to care for her. Come and stay with us!

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.

Highland Park Studio

Cozy, clean, and stylish studio apartment conveniently located in the heart of midtown Jackson near Jackson General Hospital and within walking distance of Conger Park. 1.5 miles from the University of Memphis-Lambuth campus, 2 miles from Downtown Jackson, and 3 miles from I-40. Features a full size bed that can comfortably sleep two, along with a full kitchen as part of the open floor plan.

The Pink House!

The Pink House is a city treasure! Built in 1847 and meticulously renovated in 2021, it resides on the National Registry of Historic Places. It's located within the downtown "Jackson Walk" area, and is only minutes from places like The Amp outdoor music venue, Downtown Dog Park, Jackson Farmers' Market, Hub City Brewery, Grubb's Grocery and a variety of food and drink establishments!

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!

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 Wisdom Retreat

Just 5 minutes from the hospital and Mid-Town, this historic home, featuring new appliances, brand-new furniture, and a clean, professional style, is ideal for traveling professionals, in-town guests, and mid-term stays. After a busy day, relax by the fire pit or enjoy easy access to dining, shopping, and local attractions—all within minutes.

Pet-Friendly 3BR | Fenced Yard | Office | Sleeps 7

Stay in one of Jackson's most unique pet-friendly homes. This spacious 3-bedroom, 2-bath retreat features a private office hidden behind a Murphy bookshelf door, a fully fenced backyard, covered patio, firepit, fast WiFi, and room for up to 7 guests. Perfect for travel nurses, hospital visitors, families, remote workers, and extended stays.