Vacation rentals in Medina

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.

Crown Cottages - Double Queen

Take it easy at this unique and tranquil getaway. Enjoy all that Crown Winery and West Tennessee have to offer from our great location nestled within the beautiful Tuscan-inspired Crown Winery property. You'll be joining us at our cottage nestled at the base of our breathtaking vineyard. Wake up to the stunning view of the wind blowing through the vines and "wine down" with a walk up the hill to see the sun set over the back vineyard. This 600-square-foot free-standing cottage sleeps four.

The "Heart of Milan" Guest House

This is a vintage 1920's craftsman style bungalow that has recently been redecorated. You will be renting the whole house to include a large master bedroom, a second private bedroom, two bathrooms, a fully equipped kitchen, office, living space and common room with an extra twin bed. Washer and dryer included. Hardwood floors throughout the home. This house is an ideal rental for executives or travelers who are looking for a more home like environment or anticipate an extended stay.

Cottage A at Dry Hollow Farm

Local Amish builders constructed this cabin at Dry Hollow Farm in 2021. On 63 acres of woods and pasture we raise Nigerian Dwarf and Alpine goats for milk from which we craft artisan goat milk soap of many varieties. We also raise luffa gourds and organically-grown herbs. We are located five miles outside of Huntingdon, Tennessee, and offer opportunities to interact with our farm animals and shop in our on-farm Soap Shop. We offer a peaceful rural setting with plenty of space to roam.

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.

NEW Construction-i40, Union, Shopping

The whole group will enjoy easy access to everything from this centrally located house. Beautifully appointed brand new construction home. 5 minutes from I-40, Union University, and a plethora of North Jackson stores. Close to parks, restaurants, and entertainment. Fantastic layout that features a primary with a king bed, double sinks, and large walk in closet. Remaining bedrooms feature 2 queen beds, 1 king, and 2 twin beds. Game Nook with game table. Attached two-stall garage.

Cozy apt suite/lakefront/pool /near TN Safari Park

Take a break from your hectic lifestyle & experience tranquility on our private A walk out basement guest suite with private entrance. Includes den w/ wood burning fireplace, (futon mattress ) 1 bedroom (queen mattress), bathroom w/ shower, kitchenette on a private 50ac lake. Amenities include gas grill, swimming pool , kayaking, hammock, fire pit, fishing off dock or use of jon boat. 2 miles from Gibson Co. Lake & 30 min from TN Safari Park & Discovery Park

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.

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!

Huddleston Hall

Huddleston Hall is in the heart of Downtown Huntingdon in the upstairs of a historic building that dates back to the late 1800s. Located within walking distance of restaurants, coffee shops, boutiques, and two theaters...The Dixie Performing Arts Theatre and Court Theatre makes it the perfect spot.

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.