Holiday rentals 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, 41 reviews

Farmhouse~ FIFA~Whiteman AFB~UCM~Warrensburg~Pets

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
A spacious bed is positioned near large windows, offering a scenic view of serene woodlands blanketed in snow. Soft gray bedding contrasts with the vibrant greenery outside, which is visible through the clear glass panes, creating a tranquil atmosphere.
Home in Warsaw
4.94 out of 5 average rating, 368 reviews

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!

Top 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, 55 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
The kitchen and dining area feature modern appliances and a spacious layout, with a white dining table surrounded by six chairs. Natural light enters through a large window, illuminating the room. A decorative floral centerpiece adds a touch of warmth to the table.
Home in Harrisonville
4.99 out of 5 average rating, 142 reviews

3BR/1BA Ranch Home | 45 min to KC | FIFA World Cup

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.

Guest favourite
Home in Holden
5 out of 5 average rating, 15 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.

Guest favourite
A charming exterior view of a historic home features a dark blue facade with white trim. A covered porch is visible, equipped with railings and a rocking chair. The yard is adorned with fallen leaves, and large windows allow natural light into the rooms.
Townhouse in Pleasant Hill
4.9 out of 5 average rating, 145 reviews

Rebecca's Retreat Historic Downtown Pleasant Hill

Stay in private unit in Historic Downtown Pleasant Hill, MO!!! Suite is located right on the Rock Island/Katy Trail! Beautiful 1920's home renovated into 3 private suites. This suite features a private bedroom with king memory foam bed, bath and kitchenette. Watch a movie in the spacious living area or curl up with a book. In suite laundry provided for your convenience. Kitchenette provides fridge, microwave, coffee maker(and supplies), toaster, dishes and basic cooking utensils.

Top guest favourite
The kitchen features white cabinetry with modern appliances, including a stainless-steel refrigerator and oven. A window allows natural light to enter, illuminating the countertop and backsplash. The space is organized with clear views of the sink, dishwasher, and microwave.
Home in Blue Springs
4.96 out of 5 average rating, 205 reviews

Cozy 2 Bedroom Townhouse

Newly remodeled in March of 2023. Two bedroom townhouse each with a queen bed with a half bath downstairs and full bathroom upstairs. 2-3 minutes from I-70, Walmart, Home Depot, Texas Roadhouse and many other restaurants, fast food, and shopping. Kauffman & Arrowhead Stadiums (13 miles 15 minutes) Cable Dahmer Arena (6 miles 10 minutes) T-Mobile Arena (20 miles 20 minutes) KC Zoo & Starlight Theatre (20 miles 23 minutes) Worlds of Fun (23 miles 25 minutes) NO PETS ALLOWED

Top guest favourite
Farm stay in Butler
5 out of 5 average rating, 137 reviews

The Lone Oak

Reconnect with nature at The Lone Oak, part of our working cattle ranch. Enjoy the quiet of the country while you go fishing in the pond, spotting the wildlife, and stargazing at night. Just five miles from town, right off the blacktop, and three miles from Interstate 49. The top level is a 1900 farmhouse that has been renovated and could have another group staying in it. The walk-out basement is two years old and ready for you to have a relaxing, memorable get-away.

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, 410 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.

Superhost
Home in Independence
4.86 out of 5 average rating, 771 reviews

HOT TUB Oasis Hideaway w/ 4 Bed + Large Patio+yard

Welcome to The Oasis Hideaway, nestled just 15 minutes from downtown's Power & Light District and the iconic Kauffman and Arrowhead Stadiums. Dive into relaxation with our picturesque garden-view hot tub, famously featured in a hot tub murder mystery film. Challenge friends at the pool table and make unforgettable memories. Celebrating over four years of exceptional guest experiences, we invite you to enjoy a unique stay at our serene escape!

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, 274 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.

Top guest favourite
The cottage exterior is shown, featuring a green façade with white trim. A welcoming porch extends from the front, adorned with a wooden pergola. A grassy area surrounds the home, with trees lining the background, creating a serene atmosphere.
Home in Lone Jack
4.99 out of 5 average rating, 247 reviews

Rock Valley Ranch Cottage on 15 acres, sleeps 4

Enjoy a peaceful stay at our newly remodeled cottage near Lone Jack. A beautiful property on 15 acres, overlooking a pond, roaming horses and an array of wildlife. Located just 15 minutes east of Lee's Summit and 35 minutes from the Plaza. Join us for a weekend away or stay all week with friends and family at Rock Valley Ranch!

Popular amenities for Madison holiday rentals

  1. Airbnb
  2. United States
  3. Missouri
  4. Johnson County
  5. Madison