Holiday rentals in Trenton

“The Casita Bonita”

Welcome to “The Casita Bonita” The pretty little house on 130 acres of pure bliss. My wonderful husband Jeremy and I bought 130 acres a few years back and is what we call “our farm” we have had countless picnics and bonfires, Just dreaming of doing something special on our land one day. That is where “The casita bonita” dream came true & it is our pleasure to be able to host guest just like you. I hope you enjoy your stay and the views of our land. Come back to see us soon. Love,Jeremy & Missy

Spacious and Private Guesthouse in the Country

Rustic, refined cottage with all amenities. 1930s farm home updated for modern life. Soak in the peace and quiet. Perfect for EXTENDED STAYS (CHECK DISCOUNTS!), artists/writers, looking for quiet inspiration. Full kitchen, Keurig coffee-maker, washer/dryer, stereo. Unlimited Internet through local company (TEC). Central heat/ air. Large screen TV w/ Amazon Prime. No smoking or pets, please. No minor children. Adults only. Very Private backyard. Welcome persons of all beliefs & backgrounds.

Crown Cottages - King Suite

Take it easy at this unique and tranquil getaway. Enjoy all that Crown Winery and West Tennessee has 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 beautiful 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 two.

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.

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.

Tranquil Lakeside Retreat

Relax with the whole family away from the hustle and bustle of big city life. This house sits over a quarter mile off the road on a 5-acre lake. Start your morning sipping coffee on the front porch as you watch the sunrise over the lake. End your day grilling on the back patio as the sun drops behind the backyard pond. Enjoy a day of fishing where you can catch bass, brim and catfish or just relax with a good book and enjoy the sights and sounds of nature. Here, you will find tranquility!

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.

Cozy Modern Minilmalist Stay in North Jackson

Welcome to my home in the peaceful northernmost part of Jackson, Tennessee. Our cozy and comfortable home is ideal for families, solo travelers, or business guests seeking a serene retreat with easy access to everything Jackson has to offer. This inviting space features 3 bedrooms, 2 bathrooms, Wi-Fi, smart TV and an array of kitchen utilities. Whether you’re here for a short stay or an extended visit, you’ll find everything you need for a comfortable and relaxing experience.

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

Country Cottage Home on 2 Acres Close to UTM

The whole group will enjoy easy access to everything from this centrally located place. Just down the road from the local medical businesses including the hospital and Cane Creek rehabilitation center , UTM and local shops. Quite and safe neighborhood with plenty of parking. One king bed in bedroom along with a couch and air mattresses. Extra linens included. Plenty of towels. Washer/dryer. Refrigerator,Stove,Microwave.

Simply Tea-rrific

"Quiet, cozy 3-bedroom home with 1.5 baths, nestled in a peaceful neighborhood. Centrally located in the heart of town, enjoy easy access to local amenities, charming shops, and scenic walks. Relax in the spacious backyard with a firepit—perfect for family gatherings or unwinding after work. An ideal spot for both family stays and business trips."