Holiday rentals in Jefferson County

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Top-rated holiday rentals in Jefferson County

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Rental unit in Madison

Stablemaster’s Quarters/ Best downtown location!

The historic building was originally one if the city’s main livery stables circa 1886. It has been used for several businesses in the past but has recently been converted into apartments. New furnishings, bathrooms and kitchen will be appreciated yet the historic charm is blended within. This fun river town will remind you of years gone by. Come see why Ladie’s Home Journal awarded Madison “ prettiest small town in the midwest”. Chicago Tribune says it’s “the best preserved midwest town”.

$217 SGD per night

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Cabin in Madison

Cabin on the Ridge: The Sequel

Welcome to the area's first new construction short term rental tailored for you, the guest. This contemporary cabin is nestled in the woods right in the heart of Amish country. This is the perfect destination for those who want to getaway yet enjoy the unique beauty of Historic Downtown Madison (25 minutes) recognized as "The prettiest small town in the Midwest" or chase waterfalls at Clifty Falls State Park (25 minutes). •Fast wifi •Roku TV •Keurig (K-Cups Available)

$217 SGD per night

Home in Madison

The Ogden, by Golden Retreats

Charming shotgun-style home in the heart of Historic Downtown Madison! Enjoy this recently remodeled home in the historic district. The grand fireplace leaves no room for desire- absolutely stunning feature, and it is completely functional! New updates throughout, but plenty of charm and originality. Great location! Just one block away from Madison's Main Street with local shops, restaurants, cafes, shopping, the riverwalk, and local events. Reserve it while you can!

$171 SGD per night