Vacation rentals in Madison County

4.97 out of 5 average rating, 230 reviews

Apartment in Jackson

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.

5.0 out of 5 average rating, 74 reviews

Home in Medina

The 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.

4.97 out of 5 average rating, 100 reviews

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!

4.96 out of 5 average rating, 200 reviews

A scenic view captures the entrance to The Farm at Casey Jones Village, framed by a wooden archway. Expansive green fields are dotted with rustic buildings, including a barn and sheds. A well-maintained path leads past vibrant sunflowers and seating areas, inviting relaxation amidst the natural landscape.

Bungalow in Jackson

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.

4.74 out of 5 average rating, 328 reviews

An open kitchen and living area are visible, showcasing a modern kitchenette with a black refrigerator, countertop space, and bar seating. Natural light floods the room through large windows, illuminating indoor plants and cozy decor throughout the space.

Loft in Jackson

Plant Loft in historic LANA district downtown

Introducing the Plant Loft in Jackson's LANA district, just 1 mile from Madison County General Hospital and University of Memphis Lambuth. Minutes from downtown's dining and entertainment, and a quick 3-mile drive from I-40. Sleeps 4 with a full bed and pull-out sectional. Features a kitchenette with plug in range, pots, pans, and coffee maker. Open floor plan with bathroom downstairs. Pets welcome, but kindly bring a kennel if left unattended.

Superhost

4.86 out of 5 average rating, 309 reviews

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.

A charming brick home with ivy climbing its facade is set against a backdrop of lush greenery. Dense trees provide shade over the front yard, where a well-manicured lawn and garden elements enhance the outdoor space. A welcoming atmosphere is created by the warm, rustic appearance.

4.96 out of 5 average rating, 45 reviews

"The Holiday House" Charming 3 bed 2 bath w/Pool

Enjoy a charming stay in this 3 bedroom 2 bath home with a loft and a beautiful resort style back yard with a pool. This Historical Gem built in 1940 will take your breath away. Experience a piece of history with a European feel in the Historic District of Jackson, TN. Close to all amenities and minutes from the Jackson Madison County General Hospital/Kirkland Cancer Center. 1hr & 22min drive to Memphis, TN. 2 hours from Nashville, TN.

4.96 out of 5 average rating, 50 reviews

A cozy living area is shown, featuring a plush couch adorned with a green accent pillow and a throw blanket. Sport memorabilia pennants are displayed on the wall, and a round coffee table sits in front. A kitchen area is partially visible in the background.

Apartment in Jackson

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.

4.98 out of 5 average rating, 65 reviews

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!

A spacious living area features a comfortable gray sectional couch and a blue chair, accented with patterned cushions. A round coffee table sits on a decorative rug, while natural light filters through windows, illuminating wall art and a large mirror. Greenery adds a touch of warmth.

4.91 out of 5 average rating, 211 reviews

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!

4.96 out of 5 average rating, 48 reviews

Pet-Friendly 3BR | Fenced Yard | Office | I40

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.

A welcoming front porch is shown with two rocking chairs positioned beside potted yellow flowers. A bench sits to the side, and a wooden railing surrounds the porch. Lush greenery is visible in the background, enhancing the peaceful atmosphere.