Holiday rentals in Livingston County

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.

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

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.

The Highland House- near Hamilton Quilt Town USA

The Highland House - Managed by Brad: Nestled in a scenic country location, this cozy getaway offers modern amenities and stunning views of Scottish Highland Cattle. Perfect for relaxation or adventure, guests can indulge in a country setting, and explore nearby Hamilton (Quilt Town Usa), Chillicothe (Home of Sliced Bread) Jamesport (Amish community) or simply unwind in the peaceful surroundings. Experience comfort and tranquility at The Highland House, where unforgettable memories await.

'Red Barn Getaway' Chillicothe Countryside Home

1949 Restored Barn | Antique Decor | Quiet Location Embrace the beauty of Northern Missouri at this 2-bed, 2.5-bath vacation rental! Nestled on a peaceful property with a private pond, the 'Red Barn Getaway' is your chance to slow down and enjoy the simple pleasures — lazy afternoons on the porch, homemade meals in the kitchen, and peaceful nights under the stars. Ready to explore? Stroll through Chillicothe’s historic downtown for charming shops or take a scenic drive to Hamilton.

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.

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!

The W: Historic Venue & Stay

Take a step into our grande historic home and you will feel the grandeur of the early 1900's blended seamlessly with modern design. This romantic home is full of sophisticated elegance, traditional charm and comfortable whimsy. 'The W' is the perfect guest home for a memorable experience, romantic getaway, girls weekend, family holiday, corporate retreat and full wedding weekend.

The Grove Hunting Cabin

This recently remodeled house is my hunting cabin. The location is ideal for anybody who is looking to access the many public hunting locations in north central Missouri including Fountain Grove that is right down the road. The four bunk beds are perfect to provide sleeping opportunities for 9 people with their own bed.