Holiday rentals in Madison County

4.96 out of 5 average rating, 186 reviews

A spacious bedroom features a comfortable bed with crisp white linens. Light filters through sheer curtains on either side of two windows. A wooden nightstand holds a glass lamp, while a woven basket and a clothing rack add functional elements to the inviting space.

Flat 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.

4.95 out of 5 average rating, 529 reviews

The studio features a comfortable queen size bed covered with a grey quilt and decorative pillows. A small desk with a chair is positioned next to the bed. Warm lighting enhances the cozy atmosphere, while a kitchenette is visible in the background.

Guest house in Henderson

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!**

Serviced apartment in Jackson

A cozy living area is characterized by a plush white sofa positioned on an intricately patterned red and cream rug. Colorful wall art is displayed on the teal accent wall, and a round mirror reflects the warm inviting space. Natural light enhances the ambiance.

4.94 out of 5 average rating, 65 reviews

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, farmers market, shopping, and entertainment! Also, .06 miles to the Jackson Madison Co General Hospital. The bedroom has a queen sized bed.

A spacious home is showcased, featuring a combination of stone and brick exterior elements. The entrance is highlighted by large, inviting wooden double doors flanked by greenery. Well-maintained landscaping surrounds the home, complemented by a manicured lawn and the welcoming symmetry of shuttered windows.

4.99 out of 5 average rating, 131 reviews

I'm Goin' to Jackson

Clean and cozy home less than 10 minutes from I-40, Union University, and north Jackson shopping, parks, restaurants, and entertainment. Great layout comfortably sleeps up to 8 guests yet cozy enough for 1-2 people. Our family frequents Airbnb properties when we travel and have brought that experience to our home to make it as comfortable as possible. Feel free to use the elliptical or venture outside for a walk or bike ride to see one of two water wheels and ponds in the neighborhood.

4.96 out of 5 average rating, 180 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.

4.86 out of 5 average rating, 43 reviews

A spacious living area features two comfortable sofas facing a wood coffee table, with abstract artwork displayed on the walls. A cozy rug lies beneath, and natural light fills the room through large windows partially covered by dark curtains.

Flat in Jackson

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!

4.91 out of 5 average rating, 117 reviews

The front view of a remodeled home showcases a two-story structure with a metal roof and white exterior. Large windows are framed by wooden accents. A pathway leads to the entrance, with a small pumpkin placed on the porch, surrounded by bare trees in the background.

Home in Henderson

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

A welcoming living room features a grey sofa and loveseat, arranged around a dark coffee table. A soft area rug is laid over warm wood flooring. Natural light filters through sheer curtains, enhancing the space, while decorative elements include a shelf and wall art.

4.98 out of 5 average rating, 149 reviews

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.

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.

4.92 out of 5 average rating, 181 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!

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.

4.97 out of 5 average rating, 194 reviews

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.

A comfortable living area features two spacious sofas and a cozy armchair, arranged around a decorative area rug. Soft lighting is provided by table lamps on either side. A large wall mirror reflects the space, while a piece of artwork adds a touch of color.

4.98 out of 5 average rating, 97 reviews

Our Little Tinker!

Our Little Tinker 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 with queen beds and 1 full bath.