
Holiday rentals in Madison
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Top-rated holiday rentals in Madison
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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 .

The Cottage
The Cottage, with a studio style layout, is a bright and clean space just one mile from historic downtown lees summit with local shops, bars and restaurants. The cottage is ~20 min from downtown Kansas City and 15 min from Kaufman and Arrowhead Stadium. This newly renovated 1900s milk barn is unique and special with a lot of charm, with a few of the modern conveniences. Guests are welcome to take advantage of the two acre landscaped yard and enjoy a delicious s’more at the outdoor fire pit!

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!

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*

Location! Upscale Historic home w/Chef’s Kitchen
Just steps off Downtown Historic Liberty Square, this updated 1890 home offers guests an upscale luxury experience. Be pampered in the comfortable master suite & enjoy a spa-like experience w/ large clawfoot tub, Carrera Marble shower. Chef’s kitchen includes many amenities. Enjoy meals at the large quartz island. Large private deck. Chaise couch in the living room. Home is divided into complete and private apartments. Each guest has their own entrance and no shared spaces. Wine included!

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.

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

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.

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.

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.

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.

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
Popular amenities for Madison holiday rentals
Other great holiday rentals in Madison

The Cozy Escape

Cheerful Blue-Roof Bungalow

Blind Boone Bungalow

The Lone Oak

KCcabin • Modern Wooded Retreat w/ Hot Tub

Bunks on the Farm

Grandmas’s Getaway

Blue Springs, MO - Close to Kansas City
Destinations to explore
- St. Louis Holiday rentals
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- Kansas City Holiday rentals
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- Central Illinois Holiday rentals
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- Arrowhead Stadium
- Oceans of Fun
- Kauffman Stadium
- Kansas City Zoo
- The Nelson-Atkins Museum of Art
- LEGOLAND Discovery Center Kansas City
- Harry S Truman State Park
- Knob Noster State Park
- Jacob L. Loose Park
- Mission Hills Country Club
- St. Andrews Golf Club
- Wolf Creek Golf
- Negro Leagues Baseball Museum
- Swope Memorial Golf Course
- Hillcrest Golf Course
- Indian Hills Country Club
- Milburn Golf & Country Club
- PowerPlay Metro North Entertainment Center
- Somerset Ridge Vineyard & Winery
- Fence Stile Vineyards & Winery
- Midland Theatre
- Nighthawk Vineyard & Winery




