Vacation rentals in Trenton

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.

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.

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 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.

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 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

Lakefront Barndominium | Pontoon | Sleeps 10

Wake up to mist on your own private 5-acre lake. This 40-acre lakefront barndominium sleeps 10 and comes with a pontoon boat, stocked catch-and-release fishing, a fire pit, and miles of walking trails — all just 5 minutes from Jackson, TN. Inside, the 4BR/3.5BA layout gives everyone room to spread out. Outside, grill on the covered porch, gather around the fire pit, hike the property, and take in sunsets and the kind of starry skies you forgot existed.

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.

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!

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."

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.