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Sheboygan vacation rentals

Book unique cabins, vacation rentals, and more on Airbnb

Top-rated vacation rentals in Sheboygan

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

Home in Sheboygan
River Home Getaway with River Access - Sleeps 8
Enjoy your getaway in the comfort of the River Home. With the Sheboygan River flowing through your backyard and living spaces stylishly decorated, the scene is set for a truly remarkable vacation. The eat in kitchen is equipped with all the necessities to whip up a delightful meal. The family room has a variety of board games as well as a smart TV for entertainment. The space is complete with four well appointed bedrooms. You are welcome to bring your own boat and use the private boat slip.
$213 per night
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Rental unit in Sheboygan
Sheboygan Surf House "North Point"
This deluxe studio apartments, Largest of our 3 spaces, located above Wisconsin's first Surf shop which is located in the heart of Sheboygan's Downtown District. Located directly next to bars , shopping and widely known restaurants like Tratoria Stephanos, Feild to Fork and IL Ritrovo, make walking everywhere easy. Whether you are here for Surfing and Kiting, a little get away or a wedding we are close to it all. Blue Harbor Resort, River front and the shores of Lake Michigan are close.
$76 per night
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Guesthouse in 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!
$120 per night
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Stay near Sheboygan's top sights

Photo of Blue Harbor Resort
Blue Harbor Resort27 locals recommend
Photo of Deland Park
Deland Park22 locals recommend
Photo of Bookworm Gardens
Bookworm Gardens31 locals recommend
Photo of Piggly Wiggly
Piggly Wiggly6 locals recommend
Photo of Texas Roadhouse
Texas Roadhouse3 locals recommend
Photo of Parker John's BBQ & Pizza - Sheboygan
Parker John's BBQ & Pizza - Sheboygan22 locals recommend

Cabin rentals in Sheboygan

Cabin in Sheboygan
Natural Setting Cabin close to Sheboygan/Kohler
$231 per night
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Cabin in Oostburg
Cabin: Beach Access, Lake Michigan & Kohler-Andrae
$449 per night
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Cabin in Two Rivers
Peaceful Parkside Retreat
$122 per night
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Cabin in Elkhart Lake
The LODGE in Elkhart Lake
$276 per night
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Cabin in Plymouth
Little Lake Cabin - Road America Enthusiasts!
$186 per night
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Cabin in Two Rivers
All Natural Aquamarine Cottage
$99 per night
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Cabin in Hubertus
Hugel Hutte - Log Cabin Getaway
$186 per night
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Cabin in Random Lake
The Random Cabin (On Random Lake)
$216 per night
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Cabin in Plymouth
The Cottage at Crystal Lake
$325 per night
Cabin in Valders
Cozy cabin in the woods
$325 per night
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Cabin in Manitowoc
Rustic cabin on shoreline of Lake Michigan
$309 per night
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Cabin in Hubertus
Glacier Hills Rustic Cabin #9
$63 per night

Stays in Business Drive North

Rental unit in Sheboygan
Sheboygan Surf House "Jetties"
$83 per night
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Rental unit in Sheboygan
The Garden | Sheboygan 2 Br/1Ba, Pet Friendly
$178 per night
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Rental unit in Sheboygan
Lovely modern two bedroom home with fire pit
$133 per night
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Condo in Sheboygan
Beach View Condo near South Pier
$246 per night
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Stays in James Madison

Rental unit in Sheboygan
The Beach | Sheboygan 2Br/1 Ba
$182 per night
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Guesthouse in Sheboygan
Nautical Themed Guest Suite
$114 per night
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Guest suite in Sheboygan
Modern + Minimalist 1BR Near Lakeshore Apartment!
$90 per night
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Rental unit in Sheboygan
Cozy Sheboygan Upper
$75 per night
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Stays in End Park

Rental unit in Sheboygan
Spotless Apartment Getaway near Downtown
$83 per night
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Guest suite in Sheboygan
Upper Duplex near Lake Michigan
$69 per night
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Condo in Sheboygan
Urban Townhouse
$157 per night
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Townhouse in Sheboygan
Danz Sheboygan Retreat. Newly Remodeled in 2021.
$100 per night
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