Holiday houses in Madison

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Top-rated holiday 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.

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 .

Top Guest favourite
Home in Harrisonville
5.0 out of 5 average rating, 13 reviews

NEW Beautiful 1920 house walkable 8 GUEST

Welcome to our charming 1920 home in the heart of Harrisonville, Missouri! This 4-bedroom, 2.5-baths home blends historic charm with modern comforts, offering a cozy retreat for couples, families, or friends. We are pet-friendly, so feel free to bring your furry companions along! Just a 2 min walk to the historic Harrisonville square with restaurants, coffee shops, bakery, wine bar and boutiques. This home offers easy access to the best of Harrisonville and the surrounding Kansas City area.

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 cozy living room features a gray upholstered armchair beside a large area rug. A brick fireplace with a glass front is centered beneath a flat-screen TV. Natural light enters through two windows with sheer curtains, creating a warm ambiance. Decorative plants and a wooden welcome sign add charm.
Home in Warrensburg
4.97 out of 5 average rating, 427 reviews

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.

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.

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, 134 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.

Guest favourite
Home in Grain Valley
5.0 out of 5 average rating, 19 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 serene gravel path winds through a wooded area, flanked by tall trees adorned with golden and orange autumn leaves. Soft sunlight filters through the branches, casting gentle shadows on the ground, creating a peaceful setting for a nature walk.
Cabin in Blairstown
4.82 out of 5 average rating, 287 reviews

Honey Creek Hideaway at Back Country Camp

Escape to this quiet, seemingly remote country getaway nestled down a peaceful, tree-canopied lane. Relax and unwind amid big woods, creeks, woodland trails, complete with a very large strip pit lake, and smaller lake just mere feet from your private cabin. Use our large covered dock, kayaks, paddle boat, canoe and explore all this huge waterscape and land have to offer. All manner of Missouri wildlife reside here.

Superhost
Home in Warrensburg
5.0 out of 5 average rating, 10 reviews

Tailgate Central

World Cup Ready! Tailgate Central is a newly renovated 3 bed 2 bath house with a bonus room and outdoor covered pardio! Play and stay at our sports themed getaway featuring Golden Tee, Wii, cornhole, 5 smart tv’s (1 outside), games galore and a sports bar like kitchen! Just look for the yellow house located right next to the UCM tailgate parking lot directly north of stadium across the street from Spin pizza.

Popular amenities for Madison holiday rentals