Holiday rentals in Chillicothe

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Top-rated holiday rentals in Chillicothe

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A rustic cabin stands amidst grassy surroundings, featuring a combination of wood and stone exterior. Soft lighting from the porch highlights the entrance and adds to the inviting vibe. Large windows offer glimpses of the natural landscape beyond, enhancing the peaceful setting.
Cabin in Chillicothe
5 out of 5 average rating, 14 reviews

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.

Guest favourite
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, 70 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 favourite
A bright, open kitchen and dining area features a round wooden table surrounded by four chairs. A white brick fireplace adds character to the space, while modern appliances, including a microwave and refrigerator, are neatly arranged in the kitchen.
Flat in Excelsior Springs
4.94 out of 5 average rating, 175 reviews

The Suite Spot

Originally built as The Buckley Hotel, this historic building has been brought back to life. While retaining the features that makes this home so beautiful and reflective of its time, we have brought in modern amenities that insure a comfortable stay while in the heart of Excelsior Springs. This place is so perfect if you are visiting town as it's steps from shopping, eating and landmarks. The beds are comfy with nice linens because I, for one, love a good night's rest and I bet you do too!

Guest favourite
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
4.93 out of 5 average rating, 54 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.

Top guest favourite
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.
Flat in Chillicothe
5 out of 5 average rating, 34 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.

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.
Guest house in Hamilton
4.97 out of 5 average rating, 245 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.
Apartment in Brookfield
4.93 out of 5 average rating, 121 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
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, 244 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 favourite
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, 137 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 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
4.91 out of 5 average rating, 93 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 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, 173 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.

Top guest favourite
An open living area features exposed brick walls and a wooden ceiling, creating an inviting environment. A comfortable sofa is paired with a round coffee table, surrounded by tasteful area rugs. A well-equipped kitchen is visible in the background, with modern appliances and cabinetry.
Flat in Chillicothe
5 out of 5 average rating, 72 reviews

Silver Moon Heights Loft with unique balcony

This unique place has a style all its own! This newly renovated downtown space is a one bed one bath with an open floor plan. Enjoy a trip back to the early 1900s with modern conveniences. The balcony with a sitting area overlooks Silver Moon Plaza park and stage.

Popular amenities for Chillicothe holiday rentals

Quick stats about holiday rentals in Chillicothe

  • Total holiday rentals

    Explore 10 holiday rentals in Chillicothe

  • Nightly prices starting at

    Chillicothe holiday rentals start at £60 per night before taxes and fees

  • Verified guest reviews

    Over 740 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Wifi availability

    10 of Chillicothe holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chillicothe rentals

  • 5 Average rating

    Chillicothe stays are highly rated by guests – averaging 5 out of 5!