Vacation rentals in Chilhowee

The Orchard House by Katy Trail

Dubbed the Orchard house since being on Orchard street. This newly renovated stand alone home on a quiet dead end road is just what the doctor ordered. Located just 2 miles to the start of the historic Katy Trail makes this a great spot. Also, we are only minutes away from Truman Lake which boasts some of the best crappie and spoonbill fishing around. A dedicated shed with lock is provided at the back of the home for bike storage. A short walk to the historic square with shopping + eateries!

Family · Location · Air conditioning

The Overlook

Adventure awaits! Enjoy the best sunsets and night skies from high above the shores of Truman Lake. An unforgettable way to unwind! Perfect for romantic getaways, thrill seekers, and tourists alike. Protected forests surround the neighborhood and the historic "Hallmark town" of Warsaw is minutes away. A modern marina is just down the road. Great opportunities for relaxation and recreation abound with memorable times sure to be had! Ask about our romance/birthday packages and pet friendly stays!

Family · Value · Grill

Soaking Pool • Hot Tub • 27 min to Arrowhead

Escape to KCcabin — a modern, secluded retreat in the Lake Lotawana area (no lake access). This new-build hideaway offers 2 bedrooms plus bunk beds, NEWLY ADDED soaking pool and hot tub with wooded views, spacious deck & grill, 65" smart TV, WiFi, washer/dryer, and a workspace with standing desk. Just minutes to dining, marinas, and only 30 min to downtown KC. Perfect for families, couples, or remote work getaways. If you'd like to view a walkthrough video, message me and I can send you a link.

Location · Family · Access

Farmhouse~Whiteman AFB~UCM~Warrensburg~Pets~Venue

Charming farmhouse & Venue on 80 acres with amazing sunset & sunrise views.Fully equipped home ready to host an enchanting experience.Relax with a cup of coffee and rock your stress away on the covered front porch or enjoy a freshly grilled steak next to the campfire.Bring your outdoor games & ball gloves.Complimentary bundle of firewood and outdoor camp chairs are provided.The 40x80 Venue is available to host guests for an additional fee. Pets and guests must be approved and on the reservation.

Location · Family · Amenities

The Den at Cave Hollow

A Cozy Retreat in Warrensburg, Mo! Nestled at the edge of Cave Hollow Park, The Den at Cave Hollow is a perfect getaway. Whether exploring the caves, enjoying downtown, or UCM, our location is convenient. Start your day with a hike through the trails of Cave Hollow Park. We’re also just minutes from the heart of downtown Warrensburg and Whiteman AFB. Come experience the best of Warrensburg from The Den at Cave Hollow! We look forward to hosting you. Book now and start your adventure!

Value · Family · Nearby

(White) Cabin cozy in the woods

Come enjoy a relaxing stay in the country. This cabin has a bedroom with a king size bed, a loft area with a queen bed, and a sofa bed in the LR. It has a full kitchen, bathroom, A/C, heat, WiFi. We are located an hour from KC and minutes from Whiteman AF Base, the University of Central Missouri, and Warrensburg which offers many shops and restaurants. Our Amish bulk food store is located on the premises for a unique shopping experience. EV chargers are also available. No pets allowed

Family · Location · Bathroom

Downtown Retreat with large privacy fenced yard

This updated downtown retreat has two bedrooms, 1 bath, kitchen, living room, dining room and laundry. Off street parking is behind the house. This property has a large fenced in yard with deck and firepit. Majority of the time you can catch a nice breeze in the backyard while you relax. In the winter you can enjoy the gas fireplace in the living room and stay warm. Downtown is just walking distance way with historic sites and restaurants, coffee shops and shopping.

Family · Location · Heating

Secluded 21-Acre Retreat w/ Trails, Beach & Pond

Escape to your own private 21-acre countryside retreat, complete with scenic trails, a 1-acre catch-and-release fishing pond, paddle boat and beach area. This peaceful 2-bedroom, 2-bath home offers the perfect mix of comfort, privacy & nature. Enjoy morning coffee while watching wildlife, explore scenic walking trails, or unwind under the stars in a hammock . Whether you're looking for a relaxing getaway or a place to reconnect with nature, this space delivers.

Location · Family · Pets

Rock Valley Ranch Farmhouse, 15 acres, sleeps 14

Enjoy a peaceful stay at our newly remodeled farm house in Lone Jack. A beautiful ranch set on 15 acres overlooking a pond and fenced roaming horses. Spend a weekend away to gather with friends and family, host a small group event, or business meeting! The home has five bedrooms, three full bathrooms. and an open kitchen designed for entertaining. For outdoor festivities, there are two large porches and a separate pavilion! Located 15 minutes east of Lee's Summit.

Location · Family · Nearby

Don't miss this Incredible Lakefront Farm Stay

Slip away to this tranquil and spacious lakeside home, and spend quality time with the whole family or a retreat group. Both kids and adults have plenty of opportunities to choose their own adventures; from fishing and canoeing in the 5 acre lake, to exploring the trails that roam through wooded acres and sloping hills. Simply relaxing on the back deck or screened porch to view the diverse wildlife is another perfect way to unwind during your stay.

Family · Location · Pets

Cheerful Blue-Roof Bungalow

Just a few blocks from the University, close to downtown restaurants and shops, and a short drive to the base make this Bungalow the ideal spot. This family and pet friendly home comes with a fully fenced in big backyard and is decorated in soft creams, blues and greens for a welcoming, and relaxed feel. After a day of activity, enjoy relaxing on the front porch swing, an evening of Bar-B-Que on the back deck, or a night spent around the firepit.

Value · Family · Layout

Spacious Family-Friendly Stay Near Whiteman AFB

📍 Unbeatable Central Location: 🚗 1 mile to Whiteman Air Force Base – great for visiting loved ones or temporary assignments 🌳 1 mile to Knob Noster State Park – enjoy hiking, picnicking, and scenic nature trails 🎓 8 miles to Warrensburg, MO – explore the charming college town and the University of Central Missouri 🎡 20 miles to Sedalia and the Missouri State Fairgrounds – experience one of Missouri’s biggest annual events!

Value · Location · Kitchen