Vacation rentals in Trenton

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Top-rated vacation rentals in Trenton

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Top guest favorite

A cozy bedroom features a rustic wooden bed framed by a backdrop of deep blue walls. Decorative art pieces in yellow and white adorn the wall above, while soft pillows in complementary colors are arranged on the bed. Natural light filters through a nearby window, highlighting the warm wooden flooring.

Farm stay in Jamesport

5 out of 5 average rating, 33 reviews

The "Doddy" House

Take a weekend....or a week! Travel back in time to Jamesport Mo and stay at this cozy 1 bedroom,1 bath Suite in the middle of Amish Country . Located 4 miles east of Jamesport ,this peaceful setting is sure to turn your week around! Enjoy the sunset and go for a walk, or take a tour of Mrs. Mary's Amish home... Why the "Doddy" house? Doddy houses are usually the second dwelling on an Amish farm. Generally small and built to accommodate the elderly parents after they pass on the farm to a child.

Guest favorite

The exterior of the home features a green facade with large windows that offer ample natural light. A set of stairs leads up to the front door, framed by a landscaped area and a grassy yard. A concrete driveway is visible at the base.

Home in Trenton

4.89 out of 5 average rating, 28 reviews

The Green House! Sleeps 12

Discover our spacious Trenton retreat, ideal for up to 12 guests! With two cozy living rooms, each with plush seating and TVs, there’s room for everyone to relax. Two fully stocked kitchens make meal prep easy, and the dining areas are perfect for group dinners. The large playroom is stocked with games and activities to keep all ages entertained. Located in a peaceful neighborhood, this home offers comfort and convenience for families and friends looking to explore the charm of Trenton Missouri.

Guest favorite

A single-story house is surrounded by a spacious yard, featuring green grass and shade from large trees. A porch with seating overlooks the outdoor space, inviting relaxation. The exterior is painted in light colors, and the property appears well-maintained, providing a peaceful retreat.

Home in Trenton

4.97 out of 5 average rating, 33 reviews

5 star convienient cottage Sleeps 6 Filtered water

Relax at Grandma's Cottage. Convienient. Calm. Clean. Perfect for short and long stays. * desk * roku tv * sleeps 5-6 adults. * Extra kids mattresses * Pack-n-play for baby * toys * closets * extra blankets * filtered drinking & shower water * celling fans * washer/dryer * toilet/shower bar * storm shelter * off street parking Enjoy outdoors * large yard * fire pit * swing set * bbq close to *shopping *groceries *walking trail *high school *shady park *fair grounds *restaurants *& more

Top guest favorite

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

4.93 out of 5 average rating, 30 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.

Guest favorite

A cozy living area features a light-colored sectional sofa facing a large television set atop a light wooden entertainment unit. A decorative rug with intricate patterns is placed on the floor, while surrounding plants add a touch of greenery to the space.

Home in Hamilton

4.95 out of 5 average rating, 117 reviews

Beautiful 2 BR Cottage in Hamilton

Forget your worries in this spacious and serene home located just a quick drive from Hamilton’s quaint downtown. Whether you’re visiting family, shopping at Missouri Star Quilt Company, or attending a wedding at The Pearl, you’re sure to find everything you need for a wonderful stay. This newly remodeled home features a primary queen bedroom, a second bedroom with two twin beds, a spacious bathroom, fully stocked kitchen, and ample living and dining space. You’ll feel right at home!

Top guest favorite

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

4.91 out of 5 average rating, 67 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. We do have a twin bed we can add to the lake cottage if requested.

Guest favorite

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, 117 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 favorite

A small deck area features two metal chairs with colorful patterned cushions and a round table between them. A blue lantern sits on the table, surrounded by a wooden railing and natural greenery in the background.

Apartment in Trenton

5 out of 5 average rating, 100 reviews

Oaktree Ridge

2 bedroom apartment on 2nd floor. Living room with wall mounted 55"TV, kitchen, bathroom with washing machine/dryer. Wi-fi available. Linens provided. Kitchen stocked with basic cooking gear. This apartment is located in town. We are located walking distance from Eastside park, the city walking trail, grocery stores, and fast food restaurants. We can host up to 4 people. $10/per person per day fee for 2nd and 3rd persons (including children).

Top guest favorite

A cozy open living and dining area is depicted, featuring a dining table with wooden chairs. A comfortable sofa and an armchair provide seating options, with wall art accentuating the space. Natural light enters through the nearby window, creating a bright atmosphere.

Home in Chillicothe

4.97 out of 5 average rating, 126 reviews

Cute and convenient 2 bed 2 bath

Newly remodeled interior (we are still working on the outside!!) two blocks from Walmart and two blocks from Washington Street. Good parking on and off street. Wonderful open floor plan to host a family or just a comfortable place to stay. We are going to be as pet friendly as we can but please let us know if you are bringing pets (type, sizes and number) before booking. We have carpet in the front room and bedrooms. THANKS!

Top guest favorite

An inviting living space features wooden walls adorned with mounted deer heads. A large window provides views of the lake, complemented by soft seating. A rustic-style kitchen island with red bar stools is positioned near a vibrant red stove, enhancing the functional layout.

Cabin in Gilman City

4.96 out of 5 average rating, 23 reviews

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.

Top guest favorite

A newly renovated gambrel-style barn features a combination of grey siding and large windows. A wooden bench is located on the porch area, and string lights are hung for illumination. Lush green grass surrounds the exterior, creating a tranquil rural setting.

Barn in Breckenridge

5 out of 5 average rating, 169 reviews

Relax in Rustic Luxury Overlooking Vineyard

A young vineyard planted in 2018, Catawba Vineyards boasts twenty acres of sprawling farmland property and a newly renovated gambrel-style barn to accommodate overnight guests and indoor/outdoor events. The property is currently developing and constructing its own wine-making processes to become the newest member of the growing north Missouri winery family.

Superhost

A spacious living area features a mix of leather seating arranged around a wooden coffee table. A stone fireplace serves as a focal point, with a nearby window allowing natural light. Warm lighting is provided by a floor lamp and ceiling fan.

Cabin in New Hampton

4.92 out of 5 average rating, 393 reviews

Wolf Den Lodge

This is a nice, rustic cabin located out in the country in a calm quiet atmosphere. Located a short drive from Bethany MO with access to everything you would need. There is plenty of countryside to explore as well as farm pond great for fishing about 100 yards from the back door. Great place to experience the country life and get away for a few days.