Holiday rentals in Trenton Township

Bricktown 2 Bedroom Loft

Enjoy this beautiful upstairs loft in the heart of Jamesport. Relax in our gorgeous master bedroom with Roku tv and enjoy the old fashioned claw foot bathtub with shower attached. Spacious living and dining room with beautiful wooden floors and large Roku tv. Fully furnished kitchen and a small deck to enjoy early morning. Also a second bedroom with a full size bed and Roku tv. Plenty of room for the family. Coffee and wine shops, restaurant, candle, decor, and antique shops all within 2 blocks.

Our Happy Place

Take it easy and relax....a winding dirt path leads up to the cabin’s rustic porch, where a pair of wooden rocking chairs invite visitors to sit and soak in the breathtaking view of the sunset reflecting the sky’s shifting hues. At night, the stars shine brilliantly overhead, unobstructed by city lights, while the distant hoot of an owl adds to the peaceful ambiance. A firepit nearby provides warmth and a cozy spot for quiet evenings spent under a blanket of stars... 15 min. drive to Jamesport.

Silo View (1st floor)

You’ll be renting the entire first floor of our two-story home. The second floor is not included in the rental. Welcome to our charming two-story farmhouse, over 100 years old and ideally located across from the picturesque Black Silo Winery. Ideal for weddings, family or friend visits or simply enjoying a trip to the winery which features ample parking for your convenience. Enjoy the spacious backyard, a covered patio, and a welcoming porch- ideal for morning coffee or outdoor gatherings.

“Good Enough” on Cedar

Welcome to "Good Enough" on Cedar! We fully remodeled this 2BR/1BA and accidentally made it awesome. Why pay hotel prices for a cramped room when you can have an entire private house with Netflix & fast Wi-Fi? Custom Shou Sugi Ban beds by Josh Bickford, full kitchen, laundry, ACs, porch coffee nook & a lit back deck. We are pet-friendly! Near NCMC, downtown Trenton & Adam-ondi-ahman. Perfect for traveling nurses, road crews & student families. Book today, it's way more than good enough!

The Inn on Main - Boutique BNB

Escape to this stylish and serene boutique airbnb, perfect for couples seeking a cozy, romantic getaway. Thoughtfully designed with warm tones, plush furnishings, and elegant accents, this space is ideal for unwinding together. Curl up on the luxurious leather sofa with a glass of wine or enjoy a candlelit dinner under the sparkling crystal chandelier. Whether you’re celebrating a special occasion or simply taking time for each other, you’ll find the perfect setting here. No pets allowed

Rambling Lodge

Large open area with couches, plenty of space for children and toys Small kitchen with stove, refrigerator and microwave This was formerly an office, the kitchen and half bath is small , but it’s all there. All full size kitchen appliances, Later it was used for a rental , so the washer , dryer and shower were added, which explains why they aren’t in the usual placement As this is beside HWY 36 , it’s an easy off and on. Close to town ( 1 1/2 miles to Walmart) .

Lake House: 3 BR, 3 Bath w/ handicap adaptations

NO LAKE ACCESS! The house has views of Trenton LAKE from several areas of the property! Spaces bring the OUTDOORS.. IN, with wildlife furnishings throughout. ENJOY your time by sitting on the enclosed porch or outdoor patio. Use the fully stocked kitchen to create delicious meals. RELAX in one of two living spaces. Office space, comfortable beds, spacious bathrooms, in house laundry. We hope you get out and EXPLORE what the area has to offer! Handicap Adaptations

Meneely guest house/couples getaway

Reconnect and unwind at this eclectic mid-century retreat designed for couples. Relax in the private courtyard featuring a fire pit, BBQ grill, hammock, and outdoor dining area, or enjoy morning coffee and sunset views from the spacious deck. Sleep soundly in the ultra-comfortable bed, then explore Chillicothe—the Home of Sliced Bread—where historic downtown buildings showcase beautiful murals celebrating the town's rich heritage.

Modern Home in Gallatin

Reconnect with loved ones in this family-friendly place. Fenced in backyard with a private porch. Perfect for hunters, bridal parties, weekend getaways and family! Need more space for the whole family to be together?! Ask us about our other rental right next door! 15 minutes from Missouri Star Quilt 15 minutes from History Jamesport/Amish Country Dogs must be registered before stay! We charge a $50 pet fee per stay!

Adorable 1 room lake cottage with free parking.

Peaceful lake cottage on 5 acres of lakefront property. Parking on premises. Walking distance to the Black Silo Winery. Beautiful surroundings. Perfect place to get away and relax. Includes Fiber Internet. Private owned lake for your viewing pleasure only. There is no water access included for guests. Yard and gazebo with table and chairs available to use. Sanitized and cleaned with covid precautions in mind.

Whispering Waters

Relax with the whole family at our cabin on the lake. Bring your swimming things and fishing gear and get ready for a good time! You can feed the fish, grill a delicious meal, relax in front of the tv, or soak up the sun in the water or on the sand. Spending time with friends and family on the lake will be time well spent. We also have 2 kayaks and a small fire pit there you're welcome to use.

The Cabin at the Orchard

Take it easy at this unique and tranquil getaway. Unplug and unwind in the heart of a peaceful, 1,200-tree working apple and peach orchard. Whether you're sipping coffee on the porch, wandering through rows of fruit trees, or just soaking up the quiet on the beach, this serene escape offers the perfect spot to slow down and recharge.