Holiday rentals 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 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.

Flat in Glen Carbon

4.93 out of 5 average rating, 439 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 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, 259 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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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

4.87 out of 5 average rating, 126 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.

LocationFamilyCleanliness

Top guest favourite

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, 113 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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Guest favourite

A spacious living area is characterized by a high ceiling and a mix of textures. A stone fireplace serves as a focal point, complemented by a wooden coffee table and a large television. Comfortable seating includes a brown leather chair and a grey sofa.

Home in Florissant

4.91 out of 5 average rating, 132 reviews

Cheerful 4-bedroom home with fireplace

Relax and recharge with family, friends and colleagues during your next visit to the St Louis area. This cozy home with newly remodeled bathrooms is located on a quiet cul-de-sac lined with mature trees in north county. Just minutes from highway 367 which can get you to many attractions in St Louis within 25 minutes. You can also hop right across the Illinois state line and get to towns like Alton, Granite City and Edwardsville in a short drive.

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Guest favourite

Home in St. Louis

4.96 out of 5 average rating, 148 reviews

Great Location Fam Friendly Home w/Lrg Fenced Yard

Newly finished basement with 4th bedroom (King bed), large play/relaxation space & large 120-inch projector screen and separate large speaker for movie nights! Beds are all brand new comfortable memory foam! This house is in such a great and convenient area! Freshly renovated with all brand new beds and furniture, a fully stocked kitchen for cooking and baking and a fenced in pet friendly backyard! TONS of kids and baby items!

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Top guest favourite

A bright living space is presented with a comfortable gray sofa and a round wooden coffee table. A washer and dryer are situated under the staircase, and two potted plants enhance the decor. Natural light enters through multiple windows, illuminating the area.

Cottage in Maplewood

4.98 out of 5 average rating, 555 reviews

Weaver Guest House

This charming, light-filled cottage feels like its own private hideaway, yet it's close to everything St. Louis has to offer. Tucked between trees in a quiet Maplewood neighborhood, it's a 15-minute walk to the MetroLink and a 10-minute drive to Washington University, Webster University, Fontbonne University, Forest Park, and Clayton. Business travelers and families alike will appreciate the washer/dryer, fast WIFI and cable TV.

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Superhost

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

4.88 out of 5 average rating, 105 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 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

4.89 out of 5 average rating, 125 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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Superhost

A living area is furnished with a tufted sofa and a wooden coffee table positioned on an area rug. Light flows through sheer curtains, illuminating the space. A television is mounted on the wall, and a small decorative piece sits on the console table.

Home in Caseyville

4.88 out of 5 average rating, 108 reviews

Bluebird Cottage

Make yourself at home in our newly remodeled little blue cottage, long driveway for plenty of parking and fenced in back yard perfect for pets. The cottage has 2 identical bedrooms with medium firmness memory foam mattress with a jack and jill full bathroom and bonus bedroom perfect for kids or an extra guest. Kitchen is fully stocked with cook wear and a Keurig coffee maker.

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Top guest favourite

A spacious living area is revealed, featuring a comfortable couch adorned with decorative pillows. A large area rug covers the floor, and a wooden coffee table sits at the center. Natural light fills the room through a large window, framed by soft drapes.

Home in Alton

4.97 out of 5 average rating, 158 reviews

Cozy renovated 2 bdrm cottage w/ dedicated office

Kick back and relax in this calm, stylish space that allows you to work (dedicated office space with 2 desks, monitors-great work setup) and play with amazing deck and beautiful forest view. Beautiful remodeled kitchen, updated throughout and so cozy and comfortable! Off street parking with driveway. Third bedroom is converted to an office.

ValueFamilyTV

Top guest favourite

A modern kitchen features stainless steel appliances, including a gas stove and a refrigerator. Light cabinetry provides storage, complemented by a white countertop. A window above the sink allows natural light, and a microwave is positioned conveniently on the counter.

Home in Granite City

5.0 out of 5 average rating, 31 reviews

Beautiful Remodeled Home Just Outside of St. Louis

Welcome to our updated and spacious 3-bedroom split-level home in Granite City! Enjoy a brand-new kitchen, two living areas, and a large yard with patio. Smart TVs with cable provided in every bedroom and the living room. WiFi included. Two queen beds plus a futon that sleeps two. Just 20 minutes from downtown St. Louis!

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