Holiday houses in Madison

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Top-rated holiday rentals in Madison

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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
5 out of 5 average rating, 50 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 .

Superhost
An exterior view of the Stomping Ground Studio showcases a charming house with a unique stone façade and a vibrant red front door. Two front windows are framed with dark shutters, and a set of wooden stairs leads to the upper entrance. Lush greenery surrounds the entrance.
Guesthouse in Warrensburg
4.8 out of 5 average rating, 127 reviews

Stomping Ground Studio. Quaint upstairs unit

Come experience our affordable upstairs Stomping Ground Studio apartment right here in the heart of Warrensburg and the home of the University of Central Missouri Mules! Centrally located, close to the University, and downtown Warrensburg, the Stomping Ground Studio is a peaceful spot for a small getaway. Located just north of campus within walking distance to downtown Warrensburg where you will find many bars and restaurants. Enjoy our quaint, UCM themed, upstairs studio during your stay!

Top Guest favourite
A broad driveway leads to a spacious building featuring a mix of brick and blue siding. Two garage doors are visible, framed by landscaped green areas and decorative fencing. The serene surroundings are complemented by trees in the background, creating a peaceful entrance.
Barn in Greenwood
4.91 out of 5 average rating, 195 reviews

Cozy private cottage/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*

Top 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
4.99 out of 5 average rating, 71 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!

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, 198 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
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, 141 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 living area showcases a warm blend of textures with a brown sofa and two gray chairs flanking a central ottoman. Sunlight filters through two windows, illuminating framed artwork on the walls, while a woven rug adds a cozy touch to the hardwood floor.
Condo in Warrensburg
4.99 out of 5 average rating, 140 reviews

The Dog House! Downtown Burg 2 bedrooms

Come, sit, stay in a brand new two bedroom 1 bath apartment in downtown Warrensburg-Home of Man's Best Friend! Located on the courthouse square the open concept living room and kitchen have fabulous views of downtown and the Old Drum monument. Features 2 queen beds, outdoor patio, off street parking, full bathroom and laundry room. Walk to our famous "Pine St." for food, fun and drinks and enjoy all our beautiful downtown has to offer. 4 blocks north of UCM campus and Walton Stadium.

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

Wooded Upstairs KC Escape, Cul-de-Sac, Sleeps 4

Enjoy privacy and comfort in this UPSTAIRS-ONLY retreat of a newer split-level home (built in 2021), tucked away in a quiet family friendly cul-de-sac. With wooded views and a serene neighborhood, this space offers the perfect mix of relaxation and productivity. This private upstairs retreat includes: 2 cozy bedrooms, full bathroom, fully stocked kitchen, dining room, comfortable living room, laundry room & patio overlooking the woods, perfect for morning coffee or evening unwind.

Top Guest favourite
Condo in Grain Valley
4.96 out of 5 average rating, 294 reviews

A little touch of home.

Our cozy townhome is 2 bedroom 2.5 bathroom with about 1200 square feet. We replaced the sofa sleeper 12/6/2025 for the comfort of your extra guest. We are located a few blocks off I-70 and can be at most area attractions, shopping and dining in less than 30 minutes. Kauffman & Arrowhead Stadiums (16 miles 18 minutes) Cable Dahmer Arena (9.6 miles 14 minutes) Sprint Center (23 miles 23 minutes) KC Zoo & Starlight Theatre (24 miles 27 minutes) Worlds of Fun (26 miles 28 minutes)

Top Guest favourite
A charming cottage features a welcoming front porch adorned with seasonal decorations. The exterior, painted in dark tones, is complemented by white pillars and large windows. Vibrant fall leaves blanket the yard, enhancing the natural setting. A gentle sun filters through the trees, creating a warm ambiance.
Cottage in Kansas City
4.98 out of 5 average rating, 643 reviews

Cheerful 2-bedroom cottage

Cheerful 2-bedroom cottage four miles from stadiums with free parking on premises. Family friendly with country feeling close to the city. Bathroom has a walk in shower. Large fully stocked kitchen with separate dinning area. Refrigerator with ice and water through the door. The kitchen has a dishwasher and a washer and dryer laundry area. Plus an added bonus a fully stocked coffee bar. Also added is a EV 240 volt receptacle for charging EV over night.

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.
Guesthouse in Lone Jack
4.91 out of 5 average rating, 332 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 your essentials; You also have access to the property's hot tub and 1 acre pond stocked with catfish, blue gill, and bass! The cottage has a 1 queen size bed and a mattress in the loft . Please note: we do live on this property and the cottage is next to our main house. We have friendly outdoor cats they do freely roam the property.

Guest favourite
A cozy cottage is nestled among lush greenery, with a white picket fence framing the entrance. Sunlight filters through the trees, highlighting the gentle curves of the landscape and creating a serene atmosphere. Adjacent structures are visible, surrounded by expansive farmland.
Cottage in Corder
4.88 out of 5 average rating, 312 reviews

Artist's Cottage at The Dancing Bear Farm

Get away from it all with a stay in this cozy cottage out in the middle of serene farm land. Cuddle up by the fire with a good book. Take a walk down to the pond. Enjoy spectacular bird watching. An artists and photographers dream. Enjoy watching the animals in the morning & take in a gorgeous sunset in the evening. Rustic and homey. It's a real farm after all. Your boots will get muddy but the smiles will be sunny.

Popular amenities for Madison holiday rentals

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