Madison Vacation Rentals & Ski-in/Ski-out Homes
- Collinsville
- East St. Louis
- 1.78 mi to center
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Fireplace/Heating
- Balcony/Terrace
- Parking
- St. Louis
- Grand Center
- 0.16 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- St. Louis
- Pontoon Beach
- 1.18 mi to center
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- St. Louis
- Downtown St. Louis
- 1.30 mi to center
- Fireplace/Heating
- Parking
- Air Conditioner
- St. Louis
- Pontoon Beach
- 1.53 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Fireplace/Heating
- Air Conditioner
- Internet
- St. Louis
- Central West End
- 0.51 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- St. Louis
- Central West End
- 0.59 mi to center
- Fireplace/Heating
- Pool
- Balcony/Terrace
Luxury Places to Stay in Madison
- Pet Friendly
- Parking
- Air Conditioner
- St. Louis
- Downtown St. Louis
- 0.77 mi to center
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- St. Louis
- Downtown St. Louis
- 1.39 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
- Internet
- St. Louis
- Central West End
- 0.41 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- St. Louis
- Downtown West
- 0.46 mi to center
- Hot Tub
- Fireplace/Heating
- Kitchen
- Hot Tub
- Parking
- Air Conditioner
- St. Louis
- Downtown St. Louis
- 0.81 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
Top-Rated Vacation Rentals with a Pool in Madison
- St. Louis
- Downtown St. Louis
- 0.52 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- St. Louis
- Downtown St. Louis
- 0.52 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- St. Louis
- Downtown St. Louis
- 0.52 mi to center
- Fireplace/Heating
- Pool
- Balcony/Terrace
- St. Louis
- Downtown St. Louis
- 0.52 mi to center
- Fireplace/Heating
- Pool
- Balcony/Terrace
- St. Louis
- Downtown St. Louis
- 0.52 mi to center
- Fireplace/Heating
- Pool
- Balcony/Terrace
- St. Louis
- Downtown St. Louis
- 1.12 mi to center
- Hot Tub
- Pool
- Balcony/Terrace
- St. Louis
- Downtown St. Louis
- 0.11 mi to center
- Hot Tub
- Pool
- Breakfast
- St. Louis
- Downtown St. Louis
- 1.35 mi to center
- Hot Tub
- Spa
- Fireplace/Heating
- St. Louis
- Downtown St. Louis
- 1.33 mi to center
- Oceanfront
- Hot Tub
- Spa
Pet-Friendly Vacation Rentals in Madison
- St. Louis
- Central West End
- 0.60 mi to center
- Pet Friendly
- Kitchen
- Air Conditioner
- Pet Friendly
- Parking
- Air Conditioner
- St. Louis
- Grand Center
- 0.47 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Collinsville
- East St. Louis
- 1.60 mi to center
- Fireplace/Heating
- Pet Friendly
- Kitchen
- St. Louis
- Central West End
- 0.24 mi to center
- Fireplace/Heating
- View
- Pet Friendly
- St. Louis
- Downtown West
- 0.50 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- St. Louis
- Central West End
- 0.24 mi to center
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- St. Louis
- Grand Center
- 0.47 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
Large Vacation Homes & Villas in Madison
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
- St. Louis
- Downtown St. Louis
- 1.49 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Fireplace/Heating
- View
- Parking
- St. Louis
- Downtown St. Louis
- 1.55 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Fireplace/Heating
- Air Conditioner
- Internet
- St. Louis
- Downtown St. Louis
- 1.40 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- St. Louis
- Near Southside
- 0.27 mi to center
- Fireplace/Heating
- Pet Friendly
- Kitchen
- St. Louis
- Lafayette Square
- 0.30 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
Wheelchair Accessible Vacation Homes in Madison
- St. Louis
- Downtown St. Louis
- 0.79 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- St. Louis
- Downtown St. Louis
- 1.32 mi to center
- Fireplace/Heating
- Parking
- Air Conditioner
- St. Louis
- Central West End
- 0.79 mi to center
- Breakfast
- Kitchen
- Parking
- St. Louis
- Downtown St. Louis
- 0.83 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Balcony/Terrace
- Parking
- Air Conditioner
- St. Louis
- Downtown St. Louis
- 0.65 mi to center
- Fireplace/Heating
- Kitchen
- Parking
- St. Louis
- Downtown St. Louis
- 1.28 mi to center
- Fireplace/Heating
- Kitchen
- Parking
- St. Louis
- Downtown West
- 0.50 mi to center
- Fireplace/Heating
- Kitchen
- Parking
- St. Louis
- Downtown West
- 0.46 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
Madison Resorts and Airbnb Homes Under $200
- St. Louis
- Downtown St. Louis
- 1.21 mi to center
- Fireplace/Heating
- Air Conditioner
- Child Friendly
- Child Friendly
- Security/Safety
- St. Louis
- Central West End
- 0.44 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- St. Louis
- Downtown St. Louis
- 1.06 mi to center
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Parking
- Air Conditioner
- Internet
- St. Louis
- Downtown St. Louis
- 0.69 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
Instantly Bookable Vacation Homes in Madison
- Fireplace/Heating
- Air Conditioner
- Internet
- St. Louis
- Downtown St. Louis
- 0.68 mi to center
- Fireplace/Heating
- Kitchen
- Parking
- St. Louis
- Granite City
- 3.23 mi to center
- Fireplace/Heating
- Air Conditioner
- Internet
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- St. Louis
- Downtown St. Louis
- 1.26 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Fireplace/Heating
- Kitchen
- Parking
- St. Louis
- Downtown St. Louis
- 1.36 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- St. Louis
- Downtown St. Louis
- 1.30 mi to center
- Fireplace/Heating
- Kitchen
- Parking
Book a Last Minute Place to Stay in Madison
About Madison Vacation Rentals
Explore over 1451 vacation rentals in Madison with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Madison for more space and value.
In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Madison. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Madison tailored to your preferences. On average, these rentals offer 750.43 ft² of space, and are priced at an average of US $1,178 per night.
SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Madison at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.
Top Types of Ski Accommodations in Madison
| Type | Count |
|---|---|
| Holiday Apartments | 893 |
| Vacation Homes | 359 |
| B&B | 7 |
| Cottages | 3 |
| Villas | 2 |
| Unique Vacation Rentals | 1 |
| Cabin Rentals | 1 |
Use these Quick Filters to Find a Vacation Rental in Madison
★ Pro Tip: Discover Your Ideal Vacation Rental in Madison with SunSki Resorts™. Compare a diverse array of properties, including RBO homes, vacation rentals, cottages, cabins, and more. Utilize our advanced filters to search by location, amenities, and price. Book with confidence and enjoy savings of up to 40-60% compared to a hotel stay. Create unforgettable memories with SunSki Resorts™.
Weather in Madison, IL
View the weather forecast for Madison before booking your Madison Vacation Rentals to confirm your best time to go.
Top Attractions Around Madison, IL
Sunski offers a large selection of top attractions around Madison . Research things to do on your vacation before you visit Madison.
Frequently Asked Questions About Madison?
What are the top vacation rentals in Madison?
When organizing your trip to Madison, don't miss the chance to explore the top-rated vacation rentals in the vicinity. With a plethora of options available, you're bound to discover the ideal accommodation for your stay in Madison. Peruse our collection of highly-rated properties and secure your reservation today.
- World’s Fair Charm -Two Story 3 bdrm
- Classy Midtown 2BR, King Master
- Historic Soulard King 2BR Apt w/Private Deck
- Luxury Corporate Loft Suites In Soulard
- The Dackel - Townhouse in Historic Soulard
- NEW! Luxurious Soulard Townhome w/Brewery Views!
- Luxury Brownstones in Historic Soulard
- Centrally Located Home Perfect for Family Getaway
- The Luck Dragon Loft
- Spacious 4-bedroom townhome in St. Louis
How many vacation rentals have private pools in Madison?
Uncover 13 vacation rentals boasting private pools near Madison. Explore top-rated RBO homes offering access to a swimming pool:
- Incredible 2 story city penthouse with rooftop pool, hot tub & views!
- Drury Plaza St. Louis at the Arch
- Perfectly Appointed Suite for Groups! Free Wi-Fi!
- Drury Inn and Suites St Louis Union Station
Which vacation homes or resorts in Madison are best for families?
Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in Madison. Enjoy great views, locations and save money with SunSki Resorts.™
- Heart of St Louis! Walkable Soulard Apt w/Loft
- Brick & Bed Riverfront Lofts, G 208
- Hidden Gem | JZ Vacation Rentals
How many SunSkiResorts vacation rentals or resorts are available in Madison?
Discover the ideal vacation rental in Madison with SunSki Resorts™. We provide an extensive selection of over 1451 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Madison.





































































