Vacation rentals in Chillicothe

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Top-rated vacation rentals in Chillicothe

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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, 32 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 front exterior of the house is visible, featuring a simple design with light gray siding and black shutters. A welcoming porch is adorned with purple mums in planters on both sides of the entrance, and a well-maintained lawn offers a neat appearance.

Home in Chillicothe

4.86 out of 5 average rating, 66 reviews

Crowe’s Nest

Relax with the whole family at this peaceful place to stay! Great neighborhood, very close to the Simpson park, Hyvee and YMCA. This house has a fenced backyard with a grill to enjoy. The Crowe's Nest is near the Missouri Coffee Company, The Sip, Rooted Cowgirl, Extreme Racing, Clifton's and other shopping outlets in downtown Chillicothe. It's on the North end of Chillicothe so if you're going to the fairgrounds it's close and also close to the hospital and both golfing locations. Clean Products

Guest favorite

An inviting living area is showcased with a comfortable leather sofa and armchairs arranged around a rug. A circular wooden dining table is set with decorative items at its center. Natural light filters through the windows, enhancing the warm ambiance.

Farm stay in Saint Catharine

4.96 out of 5 average rating, 141 reviews

Country farmhouse with 3 acre lake for fishing

Discover the charm of country living at our farmhouse tucked away in the quiet town of St. Catharine. Just 10 minutes from Brookfield or Marceline, this peaceful retreat is the perfect balance of seclusion and small-town hospitality. Spend your days exploring antique shops, local eateries, scenic parks and attractions like the boyhood home of Walt Disney and the birthplace of General John J. Pershing. Come relax and uncover a bit of Missouri history, we invite you to slow down and stay awhile

Guest favorite

A cozy living area is presented, featuring a dark sectional sofa adorned with orange accent pillows. A round wooden coffee table is centered, surrounded by a green armchair and a black lamp table. Two framed black-and-white photos hang on the wall, and light from the ceiling fixture enhances the space.

Place to stay in Chillicothe

4.91 out of 5 average rating, 47 reviews

Quaint on the square apartment

Centrally located walking distance to all the cute shops on the Chillicothe square. Wake up and walk across the street to the coffee shop! Shops all around the apartment. Ground floor with a view of one of our beautiful downtown murals. Walking distance to the library & much more!! SPACE NOT RECOMMEND FOR CHILDREN UNDER 12. We also have lots of board games for your liking!! Gas stove for the gourmet cook. Furnished Kitchen with pots, pans and lots misc. hope this helps! Two beds total.

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, 114 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 spacious bedroom features a well-made bed with a dark green comforter. A ceiling fan circulates air, and a small dining table is visible in the background next to a kitchenette. A doorway leads to a bright bathroom, complemented by decorative plants.

Apartment in Chillicothe

5 out of 5 average rating, 29 reviews

Master Suite - Small Town Retreat

Relax in this calm, stylish air-conditioned space located in the heart of downtown Chillicothe. Built in 1900, this newly renovated Master Suite has everything you need for an overnight date or a cozy place to sleep. It boasts an electric fireplace, large tv with Roku, huge soaker tub, and a complimentary self-serve waffle and hot cocoa breakfast eaten at the bar or on your private patio. Enjoy complimentary WiFi, a fenced backyard with fire pit and use of our pickleball equipment.

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

4.9 out of 5 average rating, 62 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.

Top 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, 115 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).

Guest favorite

The exterior of a rustic log cabin is showcased, featuring a triangular roof and large windows. A welcoming front door in a contrasting color is flanked by two smaller windows. The landscaped area includes stone accents and manicured grass, contributing to a natural setting.

Cabin in Marceline

4.95 out of 5 average rating, 241 reviews

A place to escape the busy routine of daily life.

The Circle O Lodge is located in North Central Missouri not far from historic Highway 36 and Walt Disney's boyhood home of Marceline. Families and small groups will enjoy the Circle O Lodge for its natural beauty and relaxing qualities. It is conveniently located near several local attractions. The lodge is situated on 60 acres of mixed terrain and features hardwood forests, open grasslands, 2 1/2 acre fishing pond and 15 acres of wetlands.

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, 124 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

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, 167 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.