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Sheboygan vacation rentals

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Top-rated vacation rentals in Sheboygan

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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SUPERHOST
Entire guesthouse · Sheboygan
Carriage House Sheboygan, Lake Mich beach access!
The Carriage House is the perfect getaway. Located in a beautiful historic neighborhood with Lake Michigan public beach access across the street, 100 yards away. Ideal for a family of four or an individual in town for business. Amenities have been thoughtfully placed to create the most comfortable and convenient stay for guests. We pride ourselves on ensuring you enjoy your stay with us and guarantee you'll love the neighborhood!
$122 per night
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Entire vacation home · Sheboygan
Lovely modern two bedroom home with fire pit
Newly renovated two bedroom home just a mile from the beach and five star restaurants. Enjoy a game of golf at world class Whistling Straight. Car enthusiasts will love Elkhart Lake Road America. Salmon fishing the Great Lake Michigan or just have a relaxing time around the fire pit. There is a laundry with washer/dryer, steamer and folding table. Dogs under 30 pounds. No cats sorry. Ample street parking at the front door. Backyard for dogs under 30 pounds only. Sorry cats.
$133 per night
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Entire guest suite · Sheboygan
Newly Renovated Black House Lower Level
Enjoy your stay in this eclectic mid-century modern lower unit in the heart of Sheboygan. Just 6 houses separating you from Lake Michigan! Enjoy the beach by day, and wonderful food and drink by night. Everything is within walking distance! This home is located in the historic district in town and still boasts some of its original character. This unit does come with a fully equip kitchen, bathroom and washer and drier in the basement. Come on over, the water is fine!
$115 per night

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Stay near Sheboygan's top sights

Photo of Black Pig
Black Pig9 locals recommend
Photo of Blue Harbor Resort
Blue Harbor Resort13 locals recommend
Photo of Deland Park
Deland Park11 locals recommend

Cabin rentals in Sheboygan

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SUPERHOST
Entire cabin · Oostburg
Pine Dunes Cabin by Lake Michigan & Kohler-Andrae
$385 per night
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SUPERHOST
Entire cabin · Cascade
Willows Cabin Cascade, On Lake
$711 per night
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SUPERHOST
Entire cabin · Plymouth
Little Lake Cabin - Road America Enthusiasts!
$183 per night
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SUPERHOST
Entire cabin · Manitowoc
Rustic cabin on shoreline of Lake Michigan
$266 per night
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Entire cabin · Elkhart Lake
The Cabin of Elkhart Lake
$262 per night
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SUPERHOST
Entire cabin · Campbellsport
Enjoy Log Cabin Luxury on a Lake
$225 per night
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Entire cabin · Cascade
Cozy cabin on PRIVATE lake near Sheboygan, WI.
$260 per night
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SUPERHOST
Entire cabin · Random Lake
The Random Cabin (On Random Lake)
$199 per night
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Entire cabin · Cascade
Lakefront Rural Cabin On Private Lake Community
$482 per night
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Entire cabin · Valders
Cozy cabin in the woods
$375 per night
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Entire cabin · Cascade
Newly renovated! Large luxury lakefront Cabin
$705 per night
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Entire cabin · Plymouth
Cabin moments away from Road America and Lakes
$175 per night
  1. Airbnb
  2. United States
  3. Wisconsin
  4. Sheboygan County
  5. Sheboygan