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 favorite
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.

Top guest favorite
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 favorite
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, 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 favorite
Home in Holden
5 out of 5 average rating, 14 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 favorite
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 favorite
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
4.96 out of 5 average rating, 204 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 favorite
Home in Grain Valley
5 out of 5 average rating, 82 reviews

World Cup KCcabin • 27 Min to Arrowhead • Hot Tub

Escape to KCcabin — a modern, secluded retreat in the Lake Lotawana area (no lake access). This new-build hideaway offers 2 bedrooms plus bunk beds, a hot tub with wooded views, spacious deck & grill, 65" smart TV, WiFi, washer/dryer, and a workspace with standing desk. Just minutes to dining, marinas, and only 30 min to downtown KC. Perfect for families, couples, or remote work getaways. If you'd like to view a walkthrough video, message me and I can send you a link.

Top guest favorite
Farm stay in Butler
5 out of 5 average rating, 136 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 favorite
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, 407 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 favorite
A spacious reproduction Conestoga wagon is positioned on a gravel surface, with a covered outdoor kitchen nearby. The vibrant sunset paints the sky in warm colors, while the surrounding grassy area offers an open, tranquil setting for relaxation.
Farm stay in LaCygne
4.96 out of 5 average rating, 111 reviews

Covered Wagon1 @IsinglassEstate

Isinglass Estate is anything but ordinary. Our reproduction Conestoga Wagons have it all- with heat, A/C, a full bathroom, your own private outdoor kitchen and firepit, and five star details to complement the 100acre views of the polo field and vineyards! Wagon guests enjoy access to our 600 acre estate with fishing, hiking, vineyards, blackberries, a petting zoo, horseback rides, horse-drawn carriage rides, plus a restaurant and winery tasting room all on-site.

Guest favorite
The exterior of the log home is displayed, featuring a peaked roof and large windows that allow for natural light. Surrounding greenery includes trimmed bushes and an open lawn area, creating a welcoming appearance. The structure stands prominently against a clear blue sky.
Home in Concordia
4.88 out of 5 average rating, 182 reviews

Charming Log Home

Come enjoy our log home! This home was built as a model log home. It has its own charm and beauty and is a great place to unwind if you don’t mind some road noise. High speed internet is available-but no TV The property is convenient and easy to access,with a large parking area, although being next to I70 it is not quiet and secluded, expect road noise.( ear plugs and white noise machines are provided.) There is no Laundry-A local Laundromat is available.

Guest favorite
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.

Popular amenities for Madison vacation rentals

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