Vacation rentals in Madison County

4.96 out of 5 average rating, 225 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.

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4.95 out of 5 average rating, 564 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.

Guesthouse 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!**

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A well-furnished living area features a light-colored sofa adorned with throw pillows. Natural light enters through two windows, while a potted plant adds greenery to the space. A glass coffee table rests on a traditional area rug, enhancing the room's inviting character.

4.89 out of 5 average rating, 57 reviews

Blue Bungalow on Wisdom St.

Welcome to your home away from home in the heart of downtown Jackson (LANA area). This cozy retreat is perfect for families, professionals and pet owners. Centrally located near the hospital, dining, and entertainment, it offers convenience and comfort. Enjoy the privacy of a fenced backyard, ideas for relaxing or letting your pets play. Whether you're here for work or leisure, this well-appointed space ensures a restful stay in a prime location. Book now for a comfortable, hassle free visit.

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4.96 out of 5 average rating, 196 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.

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4.86 out of 5 average rating, 308 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.

ValueFamilyOutdoor spaces

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, 164 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.

ValueFamilyGetting around

4.96 out of 5 average rating, 47 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.

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4.98 out of 5 average rating, 64 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!

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A modern kitchen space features a central island with a marble countertop, accompanied by two white stools. A wooden dining table for four is situated nearby, illuminated by a pendant light. Soft gray walls and tiled flooring enhance the clean, contemporary aesthetic.

4.98 out of 5 average rating, 45 reviews

A sweet retreat in the cove…

***Freshly remodel inside*** Relax with the whole family at this peaceful place to stay. Greet the morning with coffee while relaxing on the Private deck off the mb. Enjoy the backyard privacy fence. Convenient to shopping areas and all your best restaurants, just 2-5 mins away from Kroger- Starbuck and Hospital. “Smoke and pet free”

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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.

4.96 out of 5 average rating, 322 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.

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A spacious living area is furnished with a grey sectional sofa and two green accent chairs. A vibrant red area rug lies on the wooden floor, complementing the neutral wall color. A minimalist black fireplace and a large wall-mounted television are also present.

4.94 out of 5 average rating, 94 reviews

Jackson Sweet Retreat

Welcome to our Jackson sweet retreat!! This adorable 3 bedroom 2.5 bath is tucked away in a quiet neighborhood on a spacious corner lot under tall Tennessee trees. Centrally located in north Jackson, you are also walking distance to local shops, grocery and restaurants! Come stay awhile!

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