Holiday rentals in Madison

The Cottage on College Street

The Cottage is very cozy with a mixture of vintage and industrial decor. Visitors will have complete privacy within the house at all times, but with our home close by, we are always happy to help should you need anything! We are located in Downton Brandon in the Historic District. The Cottage is a guest house seated behind our home; it is a very quiet place, and it is great for working individuals, couples seeking a fun concert experience, or families participating in ball tournaments.

The Funky Monkey Cottage in Fondren!

The Funky Monkey is a cozy, whimsical, historic cottage brimming with charm in the heart of Fondren! The perfect spot for a quiet romantic weekend, a last-minute getaway, or a family trip to the famous Hal's St. Paddy’s day parade. Within walking distance to local restaurants, coffee shops, boutiques, movie theatre and music venues and a short drive to all major medical facilities, universities and museums. The Funky Monkey Cottage is the most unique spot for your Jackson adventure!

The Ivy House- Tiny Home in Jackson

Stay in this cozy Tiny Home! Only minutes from the Belhaven Town Center, some of the state's best restaurants, parks, and Museums, Downtown Jackson, and the famous Fondren area. Enjoy a cozy stay in the heart of the Historic Belhaven Neighborhood! The Ivy House is a fully furnished guest house with a kitchen, porch, bathroom, private entrance, and loft! Feel free to ask if you need anything during your stay or any recommendations of our favorite local attractions and restaurants!

Relax in Architecture! Secluded, Safe, and Serene.

Welcome to the Falk House! Listed on the National Register of Historic Places by the US Department of the Interior, the Falk House is a treasure of mid-century modern design. We've transformed the original art studio into a stylish, private oasis, with expansive views of nature and Eastover’s Upper Twin Lake. You will be central to all metro destinations, including amazing restaurants, bars, and shopping, as well as area hospitals, courts, and businesses. Long stays ideal.

Mannsdale Manor Bunk House

Sweetest lil Bunkhouse in the South and in the safest little city in America according to Forbes Magazine. Nestled in the pines, our guests have privacy in nature with the amenities of rural life. Our location is central to the Madison-Jackson area; easy access to shopping and fine dining; tons of charm and character; full access to pool, private patio. Ask me for special discounts for Active military, Veterans, Law Enforcement and Southwest Airline employees. Contact Pam.

Hospitable Reservoir home w/King Bed near Shaggy’s

If you want the best food, a comfortable stay, and a place that feels like home, look no further than staying on the Rez Cottage. Walking Trails, Water Activities, and Parks are nearby. This fully furnished Cottage will have the perks of Simple Luxury without the hassle of the upkeep. Come stay for a Week or an Extended Weekend to enjoy all the Reservoir has to Offer. This property has a Beautiful Master Suite with a King Bed and Two Adjacent Bedrooms with a Queen Beds

Downtown Apartment, Close to the Best of Jackson

Long-term discounts now available. Welcome to this cozy one-bedroom apartment in a quiet, safe neighborhood minutes from the heart of downtown, Belhaven university, and Millsaps. This well-lit space is part of a 1940s duplex with off-street parking and a private yard for outdoor relaxation after a long day-- perfect for business professionals and cultural enthusiasts. By default we do not allow pets, however we are open to it so please request and give details.

Jewelbox Suite w/ Private Entry - Perfect Locale

The Snooty Suite loves everybody! Smack in between downtown and Fondren (but in an awesome, old historic neighborhood in its own right), it's part of the House of Seven Gables. With a private entry, sitting room and bath, you'll have ample breathing room and the freedom to explore Jackson at your leisure. Chill on the porch, walk to the coffee shop or take a quick drive to Fondren, downtown and the museum campus.

Top of Fondren

Located in the Historic Fondren District, my place is just steps from fabulous restaurants, wine bars, coffee shops, shopping, music venues (Duling Hall), and a grocery store (Corner Market). It is also very close to University of Mississippi Medical Center, Baptist Hospital, Millsaps and Belhaven University. Enjoy private/off street parking in the bustling downtown Fondren District.