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
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, 51 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 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.
Apartment in Oak Grove
4.9 out of 5 average rating, 144 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.

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 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
The living area is detailed with a sectional sofa and a black coffee table. A ceiling fan enhances air circulation. A flat-screen television is mounted above a brick fireplace. Natural light filters through the door, leading to an outdoor space, while a dining area is visible in the background.
Home in Blue Springs
4.95 out of 5 average rating, 177 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
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
The charming cottage features a welcoming front porch with decorative railings and a vibrant red gable accent. Lush green grass surrounds the pathway leading to the entrance, which is adorned with an elegant door and large windows covered with lace curtains.
Home in Harrisonville
4.93 out of 5 average rating, 164 reviews

Emmons House, 1 min walk to Square, pet-friendly

This writer's retreat cottage is close to everything. It's a one- minute walk to historic Harrisonville Square where you find Brickhouse coffee, 1886 wine & food, Headquarters wine bar, District bar & food, Birdy's fun finds & clothing, Artisan's crafts & treats, chiropractors and medspa. Beck Event Space is just across the road. Within the house, unique treasures from around the world. Gorgeous deck space for relaxing.

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 vacation rentals

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