Holiday rentals in Madison

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Top-rated holiday rentals in Madison

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Top guest favourite
A cozy living room is highlighted by a gas fireplace, framed by a faux brick surround. Comfortable seating includes a circular coffee table and two armchairs, with soft curtains on the window allowing natural light. Decorative elements add a welcoming touch to the space.
Home in Harrisonville
4.99 out of 5 average rating, 139 reviews

3BR/1BA Ranch Home | 45 min to KC | 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
A gravel drive winds through green grass and trees, leading to the guest apartment and other structures on the 18-acre property. Bright sunlight illuminates the scene, highlighting the natural surroundings and the peaceful setting.
Flat in Oak Grove
4.9 out of 5 average rating, 153 reviews

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.

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, 360 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, the historic "Hallmark town" of Warsaw is minutes away, and a 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!

Guest favourite
The entrance of the Bohemian Lodge is illuminated at dusk, with a winding pathway leading to the front door. A cozy seating area is visible, framed by lush greenery and illuminated by soft garden lights along the path.
Guest suite in Buckner
4.94 out of 5 average rating, 164 reviews

MILO FARM-Sacred Kansas City Retreat

MILO FARM - SACRED LAND sits east of Kansas City & is a nature retreat w/ a cedar forest, a hardwood forest, 2 ponds, bohemian lodge, art studio, pool, barn, miles of trails & whimsical camping spots.  Pet and feed the farm animals while you are here! Guests have lower level of the lodge to themselves with 2 suites (with private baths), rec room, bar area, laundry, steam sauna & rock sauna, play room & patio.  Milo Farm is located just 30 minutes from KC. More info on MiloFarm.com

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, 402 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.

Top guest favourite
The exterior of the farmhouse is visible, showcasing a white structure with a dark green roof and large windows. A gravel driveway leads to the entrance, bordered by small shrubs and gathered stones. A wooden sign is positioned near the door, indicating the entrance.
Farm stay in Butler
5 out of 5 average rating, 120 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 while enjoying the hot tub. Just five miles from town, right off the blacktop, and three miles from Interstate 49. The top level is a 1900 farmhouse that is being renovated to enlarge the bnb. The walk-out basement is all new and ready for you to have a relaxing, memorable get-away.

Guest favourite
Home in Independence
4.86 out of 5 average rating, 752 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, 266 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
A charming blue cottage features a welcoming front porch with steps leading to the entryway. Lush green grass surrounds the house, complemented by landscaping and flower pots. A fence encloses the yard, providing a sense of privacy. Adjacent houses are visible in the background.
Home in Warrensburg
4.96 out of 5 average rating, 121 reviews

Colorful Cottage close to UCM

Convenient and comfortable! Our Colorful Cottage is within minutes of UCM and about 10 minutes from WAFB. We have the Cottage with all the amenities needed for a nightly, weekly, or a monthly stay. Your dogs are welcome to stay as well! Pet Policy: $30-1 dog $10-each additional Please keep dogs off of furniture at all times. Kennel if anxious or destructive when left alone. Clear waste from yard at checkout

Superhost
A charming cottage features a distinctive tower and is painted in light blue with dark blue trim. The entrance, adorned with a seasonal wreath, is flanked by a small seating area. A stone pathway leads to the steps, providing access to the welcoming porch.
Guest house in Lone Jack
4.9 out of 5 average rating, 345 reviews

Adorable cottage on Beautiful property w/ hot tub

Take it easy at this unique and tranquil getaway. Enjoy your own private cottage with all the essentials for a comfortable stay. The cozy space is just under 200 sq ft and features a queen-size bed plus a loft mattress. Guests may enjoy exclusive access to the hot tub (lower level of main house) and a 1-acre pond stocked with catfish, and bluegill.

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, 238 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!

Superhost
The charming exterior of the house showcases a front porch with a wicker chair, welcoming guests. Fresh green grass surrounds the home, while mature trees offer shade. The roof features architectural shingles, and the door is framed by a decorative design.
Home in Windsor
4.88 out of 5 average rating, 193 reviews

The Broken Spoke

"The Broken Spoke" nightly rental sits on just over a quiet acre of land only steps from the Katy Trail and minutes from local restaurants and shopping. We can accommodate up to six in the house, we have additional camping space available for larger groups upon request, as well as extended stay rates.

Popular amenities for Madison holiday rentals

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