Vacation rentals in Madison

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Top-rated vacation rentals in Madison

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

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Top guest favourite
A charming farmhouse with a covered front porch is situated on a spacious lawn, featuring a symmetrical façade and white siding. Next to it, a modern event venue with a concrete floor and wooden accents showcases large open doors framed by elegant drapery.
Farm stay in Centerview
4.98 out of 5 average rating, 46 reviews

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.

Top guest favourite
Home in Grain Valley
5.0 out of 5 average rating, 100 reviews

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.

Guest favourite
The cottage exterior features a covered front porch adorned with vibrant flower beds and greenery. A wooden deck invites relaxation, complemented by a swing and seating area. The pitched roof and large windows enhance the airy appearance, while the surrounding nature provides a peaceful backdrop.
Home in Centerview
4.98 out of 5 average rating, 56 reviews

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 .

Guest favourite
A spacious living area features a round wooden dining table with four black chairs. A green sofa is positioned near a large television, with a small decorative tree and coffee table visible. Soft lighting from a nearby window enhances the inviting space.
Home in Warrensburg
4.96 out of 5 average rating, 118 reviews

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!

Guest favourite
Home in Holden
5.0 out of 5 average rating, 16 reviews

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.

Top guest favourite
A spacious living room features plush gray sofas arranged around a soft carpet. A TV is positioned on one side, while bright lamps provide warm lighting. Decorative wall art and a 'WELCOME' sign enhance the inviting ambiance.
Home in Warrensburg
4.98 out of 5 average rating, 229 reviews

Home Away From Home

Welcome to our charming 1920s two bedroom and one bath cottage. This cozy and well-maintained space offers a unique glimpse into the past while providing all the modern comforts you need for a comfortable stay. A king, queen and pullout queen beds give you plenty of space for rest. Off street parking for up to three vehicles and a privacy fenced back yard. Whether you're visiting for business or pleasure, our 1920s two bedroom and one bath cottage is a comfortable and nostalgic retreat.

Guest favourite
Cabin in Warrensburg
4.97 out of 5 average rating, 32 reviews

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.

Top guest favourite
A serene view features horses grazing on lush green grass near a tranquil pond. In the background, the remodeled farmhouse is visible, surrounded by trees, creating a peaceful rural setting.
Home in Lone Jack
5.0 out of 5 average rating, 241 reviews

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.

Guest favourite
A green yard is surrounded by tall trees, providing shade for outdoor activities. In the foreground, a child holds a red object while standing near a cornhole game setup. In the background, chairs are arranged around a fire pit, and a hammock hangs between two trees.
Farm stay in Chilhowee
4.93 out of 5 average rating, 56 reviews

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.

Guest favourite
A charming bungalow features a white exterior with light blue accents. The front porch is highlighted by a swing and adorned with greenery. A well-maintained lawn surrounds the home, offering a welcoming first impression with ample trees and a spacious driveway.
Bungalow in Warrensburg
4.91 out of 5 average rating, 137 reviews

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.

Top guest favourite
Home in Grain Valley
5.0 out of 5 average rating, 20 reviews

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.

Guest favourite
A large family house is framed by lush greenery, showcasing a striking navy blue exterior. The two-story structure features a welcoming porch with white railings and large windows. A white picket fence borders the front yard, adding to the home's charm.
Home in Warrensburg
4.92 out of 5 average rating, 146 reviews

Your Home on Grover (Large Family House)

‘Your Home on Grover’ is a beautiful, large family house conveniently located minutes from the UCM campus. * 0.9 miles from UCM * 10 miles from Whiteman AFB The property includes 4 bedrooms (sleeps 10 total), 2 full bathrooms, driveway parking, free wifi, kitchen, a multipurpose room, 2 sitting rooms, and a large backyard. Shelves are full of books, DVDs, games, and even some gym equipment so you can make yourself completely at home!

Popular amenities for Madison vacation rentals