Trips to Madison

There are a lot of options in Madison. If you plan on staying in the Madison area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Madison:

• 1800’s restored log cabin on 26 private rolling wooded acres with sunset views
• The Chandler Hotel
• Secluded Country Home in Historic Hoosier Hills
• Stoney Creek - Sit back and unwind
• #209 Kings, River View, Deck, Bicentennial Park
• Best downtown location! Stablemasters Quarters is awarded winning! Come see why…
• The Wadsworth in National Historic District of Madison, Indiana.
• Luxurious 4 Bedroom Home in Heart of Historic Madison's Downtown
• Rustic cabin just outside of Madison!
• Beautiful and spacious 3BR historic home centrally located in downtown, Madison.

There are 1 vacation rentals with private pools near Madison. Top-rated homes that have access to a swimming pool include:

• Bestway Inn - Madison

If you are looking for a family-friendly vacation home in Madison, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Madison:

• Auralis: Sleeps 8
• Beautiful Bungalow on Main
• Hillside Inn

Currently, the total number of properties listed in 2026 is over 182 in the Madison area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Madison.