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 dining area features a large wooden table set for six, complete with plates, glasses, and napkins. A stylish central vase holds greenery. Exposed brick and light artwork adorn the walls, while a doorway leads to a well-equipped kitchen visible in the background.

Apartment in Soulard

4.85 out of 5 average rating, 495 reviews

The Best and Heart of Soulard

This is a sophisticated 2 BR unit in the heart of Soulard, St. Louis' most vibrant entertainment district, filled w/everything needed for short or long-term guests! You're steps away from great bars & restaurants & only a short drive to St. Louis’ main attractions! 🚙 1.4 miles to Busch Stadium 🚙 1.6 miles to Enterprise Center 🚙 1.5 miles to the Gateway Arch 🚙 1-2 miles to major interstates (64, 70, 44 & 55) 🚙 6 miles to Forest Park (zoo & museums) 🚙 5.4 miles to BJC & Children's Hospitals

Guest favourite

Home in Bevo Mill

4.9 out of 5 average rating, 459 reviews

Sunny South City Guest House

Newly-rehabbed & cozy guest house. Everything you need is located here in the historic Bevo Mill neighborhood. In the heart of south St. Louis city, you’re steps away from local businesses, including the picturesque, historical Das Bevo. Step into a vintage-styled oasis, featuring large windows with plenty of natural light, tall vaulted ceilings, comfy queen bed, unique fridge, breakfast bar, sizable bathroom with a large walk-in shower. Hang outside at the picnic table under cute string lights.

Guest favourite

Apartment in Benton Park Historic

4.91 out of 5 average rating, 174 reviews

King Suite • Cherokee Arts • Fast WiFi • Laundry

Stay in the heart of Cherokee Street’s vibrant arts district! This stylish 1-bedroom retreat blends 1890s charm with modern comfort, featuring a luxurious King bed, 4K Smart TV, fiber WiFi, and a fully equipped kitchen stocked with essentials. Perfect for work or play, you’re steps from galleries, vintage shops, live music, and top-rated dining. Enjoy premium linens, in-unit laundry, and a Walk Score of 87 for easy exploration. Just minutes from downtown, the Arch, and the airport. Book today!

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, 230 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.

Guest favourite

A light-filled living area features a neutral color palette with hardwood flooring. A comfortable sofa and armchairs surround a wooden coffee table, while a cozy rug adds texture. A fireplace and a television are positioned on the white brick wall, complemented by windows dressed in sheer curtains.

Home in McKinley Heights

4.96 out of 5 average rating, 234 reviews

Terra House - Lafayette Square Hideaway

This charming home built in 1925 is located in a peaceful neighborhood conveniently situated just moments from Soulard, Lafayette Square, and downtown! This prime location means easy access to a variety of restaurants, bars, and entertainment! Lafayette Square Park and hip cafes are just a stone's throw away, making it ideal for those who love to explore the local scene. The perfect combination of convenience, comfort, and character, making us an excellent choice for visitors to St. Louis!

Top Guest favourite

A view from the living area into the bedroom, showcasing a serene space with a queen-size bed dressed in crisp white linens and accented by earthy throw pillows. Natural light illuminates the room, complemented by a ceiling fan and light-toned wooden flooring.

Apartment in North Hampton

4.99 out of 5 average rating, 191 reviews

The Zen Den - Centrally Located, Calm and Tranquil

The Zen Den was conceptualized out of a desire to create a calm and peaceful oasis centrally located in the North Hampton neighborhood of St. Louis where parks, cafés, restaurants, and entertainment are only minutes away. The space features modern appliances, contrasted with soft light features and natural building materials, such as reclaimed lumber, to convey a sense of calm and tranquility. Ideal for those guests seeking to retreat at the end of a busy day exploring or remote working.

Superhost

A well-lit interior space features warm wooden flooring and a soft area rug. Natural light filters in from a nearby window, enhancing the inviting atmosphere of the room. The layout suggests a cozy and functional space suitable for relaxation or entertaining.

Home in St. Louis

4.79 out of 5 average rating, 237 reviews

Cheerful 1-bedroom, red brick, historic home

Keep it simple at this peaceful, historic, and centrally-located place. This red brick home is a piece of long-standing history (built in 1928), on a quiet one way street. It is just 5 minutes away from the airport & University of Missouri Saint Louis, and just 15 minutes from down town and central west end. It is literally central to just about any place you wish to visit in the Saint Louis area! There’s convenient and free on-street parking too! Come enjoy your time at The Ruby Brick Stay!

Guest favourite

Apartment in Soulard

4.94 out of 5 average rating, 108 reviews

Soulard King 1BR - Personal Gym and Sauna Oasis!

King 1BR apt with private gym and sauna in the heart of historic Soulard neighborhood, 5 min from Busch Stadium. Very walkable, close to restaurants, nightlife, farmer's market, & more. Sleeps up to 4 with King bed, foldaway twin mattress in closet, and single futon in living room. You’ll love the amazing location, amenities, and warm vibes. Enjoy a night out and come home to a safe, clean, apt with all you need to stay in shape while you travel. Fast wifi and ample, free street parking.

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 Caseyville

4.9 out of 5 average rating, 110 reviews

Relaxing 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.

Top Guest favourite

The bathroom features a large spa tub with a decorative tile surround, complemented by a walk-in shower with clear glass doors. A window with sheer white curtains allows natural light, and two pieces of landscape art hang on the wall above the tub. Soft green accents enhance the space.

Guesthouse in Soulard

4.98 out of 5 average rating, 186 reviews

The PS Carriage House: Spa Tub + Walk Everywhere!

Located in the heart of Soulard, a dense STL neighborhood with a French Quarter vibe and the center of St. Louis' music scene, this historic two story carriage house is close to everything (WalkScore of 92/100). After enjoying the sights, unwind in the gated patio oasis or in the large spa tub upstairs. Just a half block to the famous Soulard farmer's market and to tons of bars/restaurants (most offer free shuttles to Cardinals, Blues, STL City, and Battlehawk games).

Superhost

A bright and open living space is showcased, featuring a comfortable sofa and a television mounted above a cozy fireplace. A dining area with a wooden table is visible, adorned with a simple centerpiece. A staircase leads to the upper loft, enhancing the airy atmosphere.

Home in Soulard

4.85 out of 5 average rating, 502 reviews

The Soulard Cottage | There Is Only One

Built in 1894, this historic, free-standing Cottage is a staple in Soulard. The Soulard Cottage is steps away from McGurks, Dukes, Mollys and all of Soulard's hottest spots! Not to mention, less than a 8 minute Uber to The Arch, Busch Stadium (Cardinals), Enterprise Center (Blues), the City Museum, The Aquarium and so much more! Here for business? Perfect! Here for a game? Perfect! This cottage will give you a truly unique experience while you explore St. Louis.

Top Guest favourite

A spacious backyard patio area includes several cushioned seating options arranged around a stone table. The steps leading up to a wooden deck are visible in the background, along with the façade of neighboring buildings. Soft lighting is strung above, enhancing a relaxed ambiance.

Home in St. Louis

4.98 out of 5 average rating, 195 reviews

Top Rated | Perfect Location 3BR + Epic Game Room

Nestled in a historic two-family home, this 3-bedroom, 2-bath retreat offers comfort and convenience in a prime St. Louis location. Enjoy a game room with foosball and arcade games, a fully stocked kitchen with stainless steel appliances, and a shared patio with outdoor seating and kids’ playground. Located near the Delmar Loop, Washington University, and Forest Park, you’ll have easy access to top attractions.