Vacation rentals in Oakfield

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.

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.

I'm Goin' to Jackson

Clean and cozy home less than 10 minutes from I-40, Union University, and north Jackson shopping, parks, restaurants, and entertainment. Great layout comfortably sleeps up to 8 guests yet cozy enough for 1-2 people. Our family frequents Airbnb properties when we travel and have brought that experience to our home to make it as comfortable as possible. Feel free to use the elliptical or venture outside for a walk or bike ride to see one of two water wheels and ponds in the neighborhood.

"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

Daisey’s Homeplace

Daisey’s Homeplace is where we found and rescued our second dog, Daisey, who desperately needed a family to care and love her. We thought it appropriate to name this AirB&B in honor of her. We hope you enjoy this restful, comfy 3 bedroom/2bath home filled with beautiful antiques along with all the amenities you need. It has 4 smart TVs and a little back patio to sit and enjoy. It is located in North Jackson with many restaurants and shopping centers nearby. Come and stay with us!

The Cabin at Dry Hollow Farm (A)

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 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. Visit us online at Dry Hollow Farm.

The Sweet Pea

Welcome to The Sweet Pea – your cozy home away from home! 🌿 Tucked just off I-40 and only minutes from all the essentials, this charming gem offers the perfect mix of convenience and comfort. Inside, you'll find spacious rooms, a freshly remodeled interior and exterior, and thoughtful, stylish touches throughout. Whether you're here for a weekend getaway or a longer stay, The Sweet Pea has everything you need to relax, recharge, and feel right at home.

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.

Ceiling 163

Loft 163 is located on the Court Square in Downtown Huntingdon TN. It's on the second level of a newly renovated historic building that dates back to the late 1800's. It has amazing views and is in walking distance to The Dixie Performing Art's Theatre, Court Theatre, restaurants, coffee shop, gift shops, and more.