Vacation rentals in Chillicothe

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

“The Grove” refreshing ground floor 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.

Touch of Country 150" projector, PingPong &Karaoke

Welcome! Relax at our hidden sanctuary, just 2 mins off I-35/Hwy 36 and 50 mins from the FIFA World Cup 2026 action in Downtown KC. Enjoy a 150" projector with a popcorn machine—perfect for movies or the big game! Amenities include high-speed Wi-Fi, karaoke, ping pong, and a grill. Explore our private oasis featuring a peaceful stream with a bridge and expansive green space. Free large parking with a pull-through driveway for trucks/trailers. Only 5 mins to groceries. Book your stay today!

Sliver Moon Loft

Enjoy a stylish experience at this centrally-located loft! A stay at the Silver Moon Loft will charm you with a newly renovated yet moody historical setting perched over a bustling local coffee shop. The perfect combination of downtown energy in an easy small town. Located in the center of Chillicothe, a short 1 mile drive in either direction will take you wherever you need to go. Like to walk? Perfect! Enjoy local restaurants, spas, shopping, and scenic stops without starting your car!

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!

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) .

Meneely guest house/couples getaway

Reconnect and unwind at this eclectic mid-century retreat designed for couples. Relax in the private courtyard featuring a fire pit, BBQ grill, hammock, and outdoor dining area, or enjoy morning coffee and sunset views from the spacious deck. Sleep soundly in the ultra-comfortable bed, then explore Chillicothe—the Home of Sliced Bread—where historic downtown buildings showcase beautiful murals celebrating the town's rich heritage.

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!

Modern Home in Gallatin

Reconnect with loved ones in this family-friendly place. Fenced in backyard with a private porch. Perfect for hunters, bridal parties, weekend getaways and family! Need more space for the whole family to be together?! Ask us about our other rental right next door! 15 minutes from Missouri Star Quilt 15 minutes from History Jamesport/Amish Country Dogs must be registered before stay! We charge a $50 pet fee per stay!

The Stables Barn - 3BR w/ Game Area & Fire Pit

The Stables: unique barn-style retreat on 42 private acres near Chillicothe, MO. Blends rustic charm with modern comforts. Features open-plan living, fully equipped kitchen, pool/ping pong, fire pit, and yard games. Comfortably sleeps 10 guests. Perfect for families, groups, or peaceful country escapes. Enjoy rural North Missouri's beauty, close to Chillicothe murals and Jamesport Amish community.

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.