Holiday houses in Madison

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Top-rated holiday rentals in Madison

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A round wooden dining table surrounded by four chairs is featured in the foreground. The kitchen is visible in the background, showcasing light-colored cabinets and stainless steel appliances. A breakfast bar with additional seating is located beside the kitchen area.
Home in Granite City
4.97 out of 5 average rating, 254 reviews

Cozy 2-bedroom home minutes from ST. Louis, MO

Welcome to the Sheridan House. This cozy 2-bedroom home is located in a quiet neighborhood. It sets on a corner lot with a large back yard and a parkway across the street. Spend relaxing evenings on the patio, grilling your dinner. Or challenge your partner to a game of ping pong in the basement rec room. Centrally located, you can spend your days exploring attractions in Saint Louis, Mo, Alton and Edwardsville, IL. Just minutes from World Wide Technology Raceway, Busch Stadium, & the Arch.

Top Guest favourite
The charming front porch features a white wicker chair and a decorative wreath, inviting relaxation. Greenery surrounds the entryway, complemented by a well-maintained lawn. A gravel pathway leads from the porch to the driveway, creating a welcoming entrance to the guest house.
Home in Saint Charles
4.97 out of 5 average rating, 757 reviews

301 Guesthouse- Historic Main street-Katy Trail

Our 301 Guest House is new and completely remodeled in 2018! It’s ideal for one or two people with beautiful furnishings, great queen bed, lots of amenities, full kitchen, with big back yard and patio to enjoy outdoors too! Cable and FAST WiFi! Enjoy light Breakfast! BEST location, Great events year round within walking distance, with being only about 2 blocks from S. Main St, where there are about 100 gift shops n restaurants! Katy Trail is so close, with Spring, Summer, Fall and Xmas events!

Guest favourite
An open-concept living area features a plush sectional sofa arranged around a coffee table. Large windows provide ample natural light and views of downtown. A modern kitchen with a sleek island complements the space, while exposed concrete ceilings enhance its contemporary design.
Apartment in Downtown West St. Louis
4.94 out of 5 average rating, 134 reviews

Luxurious Downtown Loft Steps From City Museum

You and your group will adore this stunning & spacious downtown 4th floor loft located right on the popular Washington Avenue in St. Louis! You will be in a prime location and can walk to so many restaurants, cafes, shops, bars, and even attractions like The City Museum and Union Station! Cozy up on the plush couch, turn on the gas fireplace, and enjoy a gorgeous sunset view right from the living room! With a spa tub, luxury bedding/towels/bath robes, and furnishings…you won’t want to leave!

Guest favourite
A spacious living area features a comfortable seating arrangement with a brown sofa and a bright yellow chair. A round coffee table is centered on a patterned area rug, with natural light filtering through large windows dressed in light curtains. A flat-screen TV is mounted on the wall.
Home in Caseyville
4.86 out of 5 average rating, 118 reviews

The Maple Cottage

Enjoy a stylish Two bedroom cottage Nestled in the backroads of Caseyville, our charming house offers the perfect blend of comfort and convenience. The Maple Cottage is just a stone's throw away from I64 and a vibrant shopping district in Fairview Heights, making it easy to explore local boutiques, restaurants, and entertainment options. The cottage features a comfortable living area, a fully equipped kitchen for your culinary adventures, and a peaceful bedrooms designed for restful nights.

Top Guest favourite
The front of a cozy cottage features a covered porch with two black chairs positioned beside soft green shrubs. A gravel pathway leads to the entrance, while blurred trees and open space create a natural backdrop under a partly cloudy sky.
Home in Edwardsville
4.97 out of 5 average rating, 101 reviews

Cozy Chicken Cottage

Escape to your own peaceful oasis, where comfort meets tranquility, just steps away from a charming, rustic chicken coop. Immerse yourself in the serene sounds of nature on our tiny farm while you enjoy the fresh air. Start your day with a cup of coffee out on the front porch while you overlook our beautiful pond. Perfect for nature lovers, this peaceful hideaway invites you to unwind, recharge and connect with the rhythms of the country. 35 mins to downtown STL. 15 mins to Edwardsville.

Superhost
The modern home features a spacious wooden deck with steps leading to a well-maintained garden. Large glass doors dominate the front facade, allowing natural light to flood the interior. Lush trees provide a serene backdrop, complementing the inviting outdoor space.
Home in Fairview Heights
4.86 out of 5 average rating, 139 reviews

Wooded Oasis with Free Bottle of wine+brkfst

Enjoy serenity and tranquility at our modern home tucked away in a private setting just 5 short minutes from Downtown St Louis. Complementary bottled water, continental breakfast(packaged muffins) and a bottle wine will pamper you the moment you arrive.Unwind in our luxurious multifunction shower+memory foam mattress Test your swing on our scenic driving mat or unwind around the crackling outdoor fire pit. Spa and Special Occassion add-on packages available. Private off street parking.

Guest favourite
A living area features a stylish gray sofa and a patterned armchair. A modern console table stands against a textured wall, accented by a wavy light installation. A green plant adds a touch of nature to the space, alongside decorative items on the table.
Tiny home in Alton
4.9 out of 5 average rating, 241 reviews

Romantic tiny home w/ hot tub

The ultimate tiny home retreat you’ve been waiting for. This 500 sqft carriage house was built in 1906! Lovingly and meticulously curated for a perfectly romantic stay. You’ll be a short drive from the always fun Fast Eddie’s Bonair or the gorgeous riverside views. Spend the day walking the Great River Road or trying local shops and restaurants. Looking to stay in? Your space has everything you need for a cozy meal in. Put on a record and relax in your private hot tub.

Top Guest favourite
A cozy log cabin is set amidst tall trees, featuring a gabled roof and a stone foundation. The front porch is adorned with chairs and a charcoal grill, providing a shaded space. Surrounding greenery creates a tranquil, natural atmosphere.
Cabin in Brighton
4.97 out of 5 average rating, 113 reviews

Log Cabin with Breathtaking View

Relax, kick back and take in the view. Cozy log cabin nestled in the woods with a breathtaking view of a private 2 acre stocked fishing lake. Private master bedroom features queen sized bed, and attached bath. Loft sleeps four with two full beds and an air mattress. Full kitchen with stove, full size fridge, microwave and dishwasher. Living room with sofa and dining room. Charcoal Grill, fire pit, picnic area, and walking trails. Pets are welcome.

Top Guest favourite
A single-story home is shown with a light grey exterior and a well-maintained front yard featuring green shrubs. A carport is visible on the left side, while an American flag adds a touch of color near the entrance. Dense trees surround the property.
Home in Glen Carbon
4.94 out of 5 average rating, 110 reviews

Sunset Cottage - 2 King beds! Downtown Glen Carbon

Welcome to the Sunset Cottage, proudly located just off main street in Glen Carbon, IL. The house is walking distance to the Madison county Rail to Trail system (miles of paved bike, run, and walking path), Miner Park, and historic Glen Carbon. The home is also walking distance to many restaurants including Glen Carbon's gem, the Wooden Nickel. The house is a 6 minute drive to Southern Illinois University Edwardsville (SIUe) campus. Permit #2024-13

Top Guest favourite
Apartment in Soulard
4.91 out of 5 average rating, 110 reviews

Exposed Brick • Bar Next Door • Laundry• Free WiFi

Brick & Bourbon blends upscale comfort and luxury with Soulard’s iconic nightlife and charm. This stylish 1BR features exposed brick, bourbon-inspired design, luxury Queen bedding, fast fiber WiFi, 4K Smart TV, full kitchen, and in-unit laundry. Walk to Soulard Farmers Market, top bars, restaurants, and live music spots. Perfect for couples, weekend getaways, business travelers, or remote work stays. Walk Score 88.

Guest favourite
A comfortable seating area is highlighted by a mid-century modern chair adorned with a knitted throw. A stylish floor lamp stands beside it, illuminating the space. Bright curtains frame a window, while an area rug with floral designs anchors the furniture.
Home in Granite City
4.89 out of 5 average rating, 101 reviews

Haven Hideaway

Welcome to our charming two-bedroom ranch conveniently located off Interstate 270 in a quiet neighborhood of Granite City, a mere 15-minute drive from downtown St. Louis. Unwind in style with full kitchen amenities, a Roku Smart TV, high speed Wi-Fi, secure off street parking, plush king and queen beds, a cozy pullout futon in the main, plus a well-appointed laundry room with full-sized washer and dryer.

Guest favourite
A spacious living area features a large, comfortable sectional sofa adorned with decorative pillows. A contemporary piece of art hangs above it, while a soft area rug adds texture to the floor. Natural light filters in from a doorway leading to the kitchen.
Home in Jennings
4.9 out of 5 average rating, 116 reviews

Cozy home in St. Louis - 7 minutes from airport

Enjoy your stay in this cozy yet stylish 2 bedroom home. Centrally located, 7 minutes from airport and within 15 mins from major attractions in St. Louis. This home accommodates all of your basic needs. One bedroom has a comfy queen bed and the 2nd holds a full size day bed with a twin pull out at the bottom. The kitchen is fully equipped for cooking. Let this be your home away from home.

Popular amenities for Madison holiday rentals