Vacation rentals in Madison County

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Top-rated vacation rentals in Madison County

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Top guest favorite

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.

Apartment in Jackson

4.96 out of 5 average rating, 178 reviews

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.

Guest favorite

The living room features a comfortable sofa adorned with yellow cushions, paired with a blue armchair and a textured ottoman. A round wooden coffee table sits on a patterned rug, with a wall-mounted flat-screen TV and a decorative plant nearby, brightened by natural light from the windows.

Home in Jackson

5 out of 5 average rating, 15 reviews

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.

Top guest favorite

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.

Guesthouse in Henderson

4.95 out of 5 average rating, 525 reviews

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!**

Guest favorite

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

4.96 out of 5 average rating, 178 reviews

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.

Top guest favorite

Home in Jackson

4.95 out of 5 average rating, 295 reviews

"Hospitality House"3 br 2 bth house N Jackson TN

You are renting the entire property. 3 bedroom 2 bathroom house with patio. Located in north Jackson close to I 40, restaurants, and shopping. Great quiet Cove neighborhood safe for evening walks. Will accommodate families, traveling nurses, students, or corporate traveler. No pets. Exceptions can be made, contact host. No large parties or events can be hosted. 10 or more pl. Non smoking home smoking in this property will result in $250 cleaning fee Quiet time between 9pm-6am

Top guest favorite

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.

Apartment in Jackson

4.92 out of 5 average rating, 49 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, great farmers market, great shopping, and great entertainment! Also, .06 miles to the Jackson Madison Co General Hospital.

Guest favorite

A single-story home features light beige siding, contrasting dark shutters, and a welcoming front porch. Decorative shrubs flank the entryway, and a circular wreath is displayed on the door. A garage is visible on the right side, with a well-maintained yard surrounded by trees.

Home in Jackson

5 out of 5 average rating, 6 reviews

I'm Goin' to Jackson, Too

Welcome to our cozy 3BR/2BA home in North Jackson! Enjoy vaulted ceilings, a gas fireplace, and a spacious eat-in kitchen with modern appliances. The master suite includes a walk-in closet, and the large fenced backyard offers added privacy. Located in a quiet neighborhood with easy access to I-40, shopping, and dining—perfect for families, professionals, or a relaxing getaway. Enjoy fast Wi-Fi and garage parking!

Top guest favorite

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.

Home in Jackson

4.98 out of 5 average rating, 142 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.

Top guest favorite

The exterior of The Pink House is illuminated at night, highlighting its classic architectural features. The pink facade is framed by dark window shutters, and the surrounding landscape is neatly maintained, with subtle lighting accentuating the home's charm.

Home in Jackson

4.98 out of 5 average rating, 49 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!

Top guest favorite

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.

Home in Jackson

4.96 out of 5 average rating, 168 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.