Vacation rentals in Madison

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!

Location · Value · Hiking

3BR/1BA Ranch Home | Quiet | 35 Min to Kansas City

Just 40 minutes south of Kansas City in Harrisonville, MO! Come enjoy an updated three bedroom home with a fully stocked kitchen, two queen bedrooms and two twin bunks. There is one bathroom with tub and shower. During the fall and winter months, cozy up in the warm living room with a gas fireplace and a good book. An inviting back yard is perfect for grilling out, playing games and enjoying the quietude of a peaceful mid-century neighborhood. Full size washer/dryer use in unfinished basement.

Value · Location · Parking

The little White Cottage

Nestled in the heart of the countryside, our charming country cottage exudes an irresistible allure. With its quaint pitched roof, inviting flower-beds grassy pathways, and breathtaking sunset views that leave you speechless , it's a haven of rustic elegance. The gentle rustling of deer in the woodsy landscape and the distant calls of birds provide a serene soundtrack to your stay. The cottage's interior is a blend of vintage charm and modern comforts. We are positive you will love your stay .

Location · Family · Wifi

Private, quiet, safe. I-70 access. Close to KC.

Sleep peacefully in this 600 square foot fully furnished guest apartment located off I-70 frontage in Oak Grove on 18 acres with 2 ponds and rolling pasture. A gravel drive leads to the property where you'll have a concrete parking place and a step-free, pavestone walkway to the front door of the apartment. Rest soundly on a queen size Tuft n Needle mattress in a bedroom with room darkening shades and various pillows to satisfy your comfort. Fully equipped kitchen, laundry room, 2 smart TVs.

Value · Location · Wifi

Spacious Country Apartment with Modern Amenities

Welcome to Louisburg! Spacious, private entry, 1000 sq. ft. apartment above detached garage within minutes of wineries, antiques & Cider Mill. Set on 15 acres, and 2 miles down a gravel road, you are out of the city and seeing stars, with an amazing 2nd story view. Sleeps up to 6 with separate bedroom with queen bed and low ceiling (62” great for kids!) loft with 2 twins & a double. All wrapped in unique finishes including an amazing shower! Located only 45 minutes from downtown Kansas City!

Location · Value · View

Cozy Private Barndominium/studio

Private studio on the second level of our detached garage behind our main house. Located in a resort-like property. Quiet and safe neighborhood. Minutes from downtown Lee's Summit. Coffee shop/bakery within walking distance. Several restaurants close by, 1 mile to iconic antique malls. Perfect place for traveling professionals. Close to Hwy 291. We use the garage for storage and to work on our vehicles occasionally, you might hear us working. *There is no smoking/vaping in the apartment*

Family · Value · Access

Secluded 21-Acre Retreat w/Trails & Creek

Escape to your own private countryside retreat on 21 acres at B&S Creekside Retreat. 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. Inside, you'll find a clean, comfortable home with everything you need for a stress-free stay.

Family · Location · Outdoor spaces

Lone Jack Cabin - Studio Suite

Beautiful private log cabin suite, conveniently located just east of the Kansas City Metro with great highway access. Close to wedding venues: Lone Summit Ranch, Powell Gardens and Stonehaus Winery. All the comforts of home! The suite features a king bed, sitting area with gas fireplace, private bath with shower, whirlpool jetted tub and kitchenette. The kitchenette includes a full-size refrigerator, small stove/oven, microwave and sink. Electric grill on private deck.

Value · Location · Grill

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.

Value · Location · Bathroom

Cozy Cabin #4

Country cabin located close to Warrensburg which is home to UMC, Whiteman Air Force Base and Clinton. Enjoy a quiet stay in the country at our modern cabins. Cabin #4 has one bedroom with a queen sized bed, as well as a queen size sofa bed. We offer a full kitchen, full bath, A/C, heat, as well as WiFi. Our Amish Bulk Food store is located on the property for a unique experience in shopping. Additionally, there are two EV chargers available adjacent to the store.

Location · Family · View

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.

Family · Location · Comfort

Sunrise Lake House- Private 12 acre lake with pool

Sunrise Lake Reserve Private Luxury Lakefront Retreat- only 16 miles from Arrowhead Stadium/GEHA Field- where the World Cup will be played in Kansas City. Welcome to Sunset Lake Reserve, a private waterfront escape designed for unforgettable gatherings, peaceful family getaways, and intimate celebrations. Nestled on a secluded 12-acre private lake just outside Kansas City, this luxury lake house blends refined comfort with natural beauty.

Location · Family · Hospitality