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 well-lit outdoor space is presented, featuring a wooden walkway leading to a cozy fire pit surrounded by natural landscaping. Soft string lights create a warm ambiance, enhancing the serene atmosphere of the wooded area, perfect for evening gatherings.

Apartment in Glen Carbon

4.93 out of 5 average rating, 426 reviews

Edwardsville Apartment - The Woodland Suite

The apartment in the lower level of the home has recently been renovated, with a walk-out private entrance, a full kitchen & dining area, full bath, bedroom and a cozy living space. Situated just 35 minutes from downtown St Louis, in the safe and affluent community of Edwardsville, this property sits in a quiet cul de sac on a wooded lot right in the heart of the city. We are just a few minutes from the SIUE campus, Edwardsville HS, & I-270. Coffee/restaurants/shops/parks/trails just 2 min away.

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Top guest favorite

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.

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Top guest favorite

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, 760 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!

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Guest favorite

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, 135 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!

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Guest favorite

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

4.87 out of 5 average rating, 120 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.

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Top guest favorite

The exterior of a charming bungalow is illuminated at night, showcasing a welcoming front porch with rocking chairs. A large, circular wreath adorns the bright red front door. Nearby, an American flag gently waves, set against a backdrop of landscaped greenery.

Home in Edwardsville

4.99 out of 5 average rating, 109 reviews

Historic Leclaire Cottage on the Park

Be part of the Leclaire National Historic District by calling this timeless, updated 1927 bungalow home for two nights, two weeks or longer! This is a quiet neighborhood full of friends who stop to chat in the twilight. Set your phone down, relax on the porch and let Leclaire take you to a simpler time. Inside, find two separate living rooms w/smart TVs. 2 Qn BDRMS downstairs, 2 twin beds upstairs. Full kitchen&bath stocked with essentials. Complimentary EV charging at N.O. Nelson campus.

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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, 141 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.

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Guest favorite

Apartment in Soulard

4.93 out of 5 average rating, 163 reviews

Rustic Lodge • Walk to Bars • Fiber WiFi • Laundry

Escape to Rustic Retreat in the heart of Soulard—St. Louis’ most walkable historic neighborhood. This cozy 1BR blends cabin-style charm with modern comfort: plush Queen bed, premium linens, fast fiber WiFi, Smart TV, full kitchen w/ Keurig, and in-unit washer/dryer. Step outside to Soulard Farmers Market, top bars, live music, and restaurants. Minutes to downtown, Busch Stadium, and the Arch. Perfect for couples, business travel, or weekend escapes. Walk Score 90. Book now!

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Guest favorite

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, 242 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.

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Top guest favorite

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, 115 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.

LocationFamilyHospitality

Guest favorite

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.

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Guest favorite

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, 118 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.

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