Holiday houses in Trenton

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Top-rated holiday rentals in Trenton

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Superhost
The exterior of the two-story farmhouse features a welcoming porch with white railings, complemented by a neatly trimmed lawn. Large windows framed by light-colored siding allow for natural light. The surrounding area includes a freshly cut green lawn, providing an inviting atmosphere.
Home in Trenton
5 out of 5 average rating, 3 reviews

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.

Guest favourite
A master bedroom features a spacious bed with white bedding against a whitewashed brick wall. The ceiling showcases exposed wooden beams, and light filters through sheer curtains. A bedside table is positioned next to the bed, contributing to the room's overall warmth.
Apartment in Jamesport
4.93 out of 5 average rating, 44 reviews

Bricktown 2 Bedroom Loft

Enjoy this beautiful upstairs loft in the heart of Jamesport. Relax in Luxury in our gorgeous master bedroom 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 the early morning. Also a second bedroom with a full size bed and tv. Plenty of room for the family. Coffee and wine shops, restaurant, candle, decor, and antique shops all within 2 blocks.

Top Guest favourite
A stylish entryway features a round neon sign stating 'THE INN ON MAIN', illuminating the space with a vibrant purple hue. A simple black chair is positioned beside a potted plant, while a cozy blanket rests draped over the chair, contributing to the boutique atmosphere.
Apartment in Trenton
5 out of 5 average rating, 13 reviews

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

Superhost
The exterior of the home features a charming white facade with a gray roof. A gravel driveway leads to a spacious porch area with seating. Sunlight filters through the trees, creating a natural warmth, and a well-kept lawn surrounds the property.
Home in Trenton
4.85 out of 5 average rating, 47 reviews

Country Good Time

Trenton Escape! Perfect for work, reunions, groups. Spacious 4BR home offers comfort, entertainment, & easy access to Trenton attractions. Imagine gathering in large living areas, relaxing in comfortable bedrooms, and enjoying our well-equipped kitchen. Upstairs, a dedicated game room promises hours of fun! While we have one bathroom, we provide extra towels & ample supplies for larger groups. Guests love our spacious layout, game room, comfy beds, great location, & thoughtful amenities.

Top Guest favourite
The kitchen and dining area feature modern stainless steel appliances and a table for four. A patterned rug adds texture to the space, which is illuminated by natural light from a nearby window. The minimalist design emphasizes functionality and comfort.
Guesthouse in Hamilton
4.97 out of 5 average rating, 253 reviews

Spacious 1 BR Carriage House - 2 min walk to MSQC

The Carriage House apartment is located behind the historic home we've restored in Hamilton. The property is nestled one block between popular Main Street shopping (featuring the Missouri Star Quilt Co. shops) and the Missouri Quilt Museum. Everything is within easy walking distance from this beautiful, newly built apartment. Plus, you'll enjoy plenty of space, a full kitchen, free wi-fi and free laundry on site. We can't wait to welcome you to your home away from home!

Top Guest favourite
The entrance features a concrete pathway leading to a glass door, framed by two hanging flower baskets filled with vibrant pink blooms. Potted plants with colorful flowers are positioned on either side of the door, enhancing the welcoming appearance of the entrance.
Condo in Brookfield
4.92 out of 5 average rating, 128 reviews

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) .

Top Guest favourite
A private deck features natural wood flooring with a unique design accommodating two trees. Two cushioned chairs and a chiminea are positioned on the deck, providing an inviting outdoor space surrounded by greenery and a lattice screen for added privacy.
Home in Jamesport
4.97 out of 5 average rating, 94 reviews

Quaint 2 Bedroom Home In Jamesport With Deck

Your family will be close to everything when you stay at this centrally-located place. This quaint home has a full kitchen, dining room, laundry, and freshly remodeled bathroom. It has 2 small bedrooms with full beds and a king size bed in the living room. The back deck is very private and was uniquely built around the trees. There is free Wifi provided, but there is no TV. Smoking is not allowed inside or outside at this property.

Guest favourite
A simple cottage exterior is displayed, featuring green siding and a white door. A large window is visible beside the entrance. Gravel paths surround the cottage, leading to a small landscaped area with stones. The sky shows soft, scattered clouds above.
Guesthouse in Trenton
4.92 out of 5 average rating, 76 reviews

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.

Top Guest favourite
The charming exterior of the tiny home is showcased, featuring a white wooden façade and a sloped roof. A small porch steps lead to the front door, with a single white rocking chair positioned nearby. Lush green grass surrounds the home, providing an inviting outdoor space.
Tiny home in Kingston
4.93 out of 5 average rating, 117 reviews

Quilters Getaway

This dreamy tiny home is the perfect getaway. Located just 8 miles from the Quilt Town of Hamilton. Featuring a twin size daybed/sofa on the main level and a full size bed in the loft. Kitchenette with microwave, coffee pot and refrigerator. TV with DVD player (and movies to pick from) and a nice selection of books. Located on a 1/2 acre lot with a park across the street and library a block away.

Top Guest favourite
A welcoming sleeping area is structured with a spacious bed in the center, flanked by two sturdy bunk beds. Soft curtains frame the window, allowing natural light to fill the room. A simple rug lies on the floor, adding warmth to the modern wood-paneled interior.
Cabin in Trenton
5 out of 5 average rating, 18 reviews

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.

Superhost
A single-story home with a welcoming front porch is set against a backdrop of autumn foliage. The porch features wicker seating, and a clear path leads to the front steps. Abundant green grass surrounds the home, creating an open, inviting environment.
Home in Trenton
4.78 out of 5 average rating, 98 reviews

Cheerful 2 Bedroom Home In Trenton City

Your family will be close to everything when you stay at this centrally-located home. Located right in the heart of Trenton, MO. It is easily accessible with plenty of parking in the back driveway. It also has a beautiful front patio to sit and relax while watching your kids play at the city park just across the street.

Top Guest favourite
A modest single-story house is shown with light blue siding and a welcoming wooden front porch. A small set of stairs leads to the entrance. The house has a garage on the right, with a driveway made of gravel and grass surrounding the area.
Home in Gallatin
4.94 out of 5 average rating, 144 reviews

Home away from home

Your family will be close to everything when you stay at this centrally-located place. You will be staying 13 miles from Hamilton, which has several quilt stores. 11 miles to Jamesport, with several stores and Amish community. 9 miles to Jameson and Historic Adam-ondi-Ahman.

Popular amenities for Trenton holiday rentals

  1. Airbnb
  2. United States
  3. Missouri
  4. Grundy County
  5. Trenton