Holiday rentals with a fire pit in Madison County

Pool House in Midtown - Centrally Located

Kick off your shoes and enjoy your stay at our spacious 1950’s home featuring large living areas, a full-size kitchen, in-ground pool, and more! Situated just 3 min from Jackson General Hospital, a short trip to the local eateries and shops of downtown Jackson, 5 mins from UofM - Lambuth and 10 mins away from the shopping and resturants of North Jackson along with Union University. Our midtown home is perfectly situated for the traveling business person, nurse, family, and more! Pets welcome!

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.

*EV Charger* -Near Union-Southern Hospitality

Charming updated smart-home equipped EV Charger. You will never want to leave this comfortable 3 bed/2 bath home in Jackson. Located off I-40, close to Union University, and restaurants. Lighting fast fiber internet and work-from-home station. Wake up enjoying a morning latte with our complimentary latte machine. You will love the outdoor space with gas fire and seating. This pet-free, spacious home sleeps up to 8. You will love how clean and comfortable your stay will be!

The Hacienda North

Welcome to North Jackson Haven! Perfect for business or leisure, our tranquil retreat offers ample space to relax. Conveniently located off Interstate 40 near Exit 85, we're less than 10 minutes from West TN Health Care and Kirkland Cancer Center, and a quick 5-minute drive to Pringles Park and the Industrial Park. The area is surrounded by major industrial players like Delta Faucet, Toyota Boshoku Tennessee, and Kellanova, making it an ideal hub for business travelers.

Rhodes Home of Henderson

Feel like you're relaxing at grandma's house with a peaceful stay in the country — only 1.5 miles from downtown Henderson. This completely renovated home retains its 1944 charm, while providing you with modern comforts, spacious walk-in tile showers, all new appliances, great mattresses, washer, dryer, fast WiFi and an open floor plan. Reserve this home at a cost comparable to two hotel rooms, and enjoy privacy, space to gather and cozy areas to relax or nap alone.

"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.

Hidden Gem

Welcome to the Hidden Gem! Relax and unwind in this comfortable three bedroom home in Jackson, Tn. Just minutes away from the city’s main attractions. When ready, enjoy the spacious home and the many amenities it come with: •Cozy bedrooms with king/Queen bedding •Fully equipped kitchen •Office desk •Free WiFi •Smart tv’s •Washer/Dryer •Pool •Outdoor patio area *PLEASE BE ADVISED ABSOLUTELY NO PARTIES OR EVENTS ALLOWED

Hot Tub Retreat • Private Fishing Pond • Sleeps 12

Bring the whole family to this inviting 70’s split-level retreat with plenty of space to relax and gather. Enjoy the bonus room, outdoor patio, and pond deck. Step outside for a soak in the hot tub, outdoor games, or peaceful catch-and-release fishing at the private pond. Inside features 5 TVs, foosball, piano, and record player. Minutes from I-40, dining, shopping, and 15 minutes to Tennessee Safari Park.

The Crescent Moon House

Located in a quiet neighborhood within the the downtown "Jackson Walk" area, but only minutes from places like The Amp outdoor music venue, Downtown Dog Park, Jackson Farmers' Market, Hub City Brewery, Grubb's Grocery and a list of food and drink establishments! Regardless if you're coming for an event, business or play, the Crescent Moon house is ready to help you put up your feet and relax!

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.

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!

Luxury Barn, 40 Private Acres w lake Near Jackson

Private 40-acre lakefront retreat just 5 minutes from Jackson, TN. This 4BR/3.5BA barndominium sleeps 10+ and features a 5-acre stocked lake with catch-and-release fishing and a pontoon boat ready to enjoy. Relax by the fire pit, grill on the covered porch, explore walking trails, and take in stunning sunsets and starry skies. Perfect for family weekend getaway or a peaceful escape.