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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.

Rental unit in Sheboygan
Sheboygan Surf House "North Point"
This newly renovated deluxe studio apartments is right above EOS Surf Shop, 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.
$70 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!
$92 per night
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Rental unit in Sheboygan
Sheboygan Surf House "The Elbow"
Located just 24 steps above Wisconsin's first Surf Shop, EOS Surf. Our newly remodeled Urban living oasis is a studio and a half that is conveniently located in the heart of downtown, just steps from renown bars and restaurants and only blocks to Lake Michigan, The Sheboygan River, South Pier and Blue Harbor. Whether you are here for adventure sports like Surfing on the Great Lake or leisure time SSH is perfect for you.
$64 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 Piggly Wiggly
Piggly Wiggly6 locals recommend
Photo of John Michael Kohler Arts Center
John Michael Kohler Arts Center60 locals recommend
Photo of Parker John's BBQ & Pizza - Sheboygan
Parker John's BBQ & Pizza - Sheboygan22 locals recommend
Photo of Texas Roadhouse
Texas Roadhouse3 locals recommend

Cabin rentals in Sheboygan

Cabin in Sheboygan
Natural Setting Cabin close to Sheboygan/Kohler
$188 per night
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Cabin in Elkhart Lake
The LODGE in Elkhart Lake
$145 per night
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Cabin in Oostburg
Cabin:Seasonal Hot Tub Lake Michigan/Kohler-Andrae
$386 per night
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Cabin in Random Lake
The Random Cabin (On Random Lake)
$121 per night
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Cabin in Plymouth
Little Lake Cabin - Road America Enthusiasts!
$198 per night
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Cabin in Two Rivers
All Natural Aquamarine Cottage
$99 per night
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Cabin in Campbellsport
Enjoy Log Cabin Luxury on a Lake
$275 per night
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Cabin in Manitowoc
Rustic cabin on shoreline of Lake Michigan
$266 per night
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Cabin in Plymouth
The Cottage at Crystal Lake
$325 per night
Cabin in Cascade
Rustic Chic Cabin in Kettle Moraine
$330 per night
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Cabin in Cascade
Willows Cabin Cascade, On Lake
$675 per night
Cabin in Valders
Cozy cabin in the woods
$325 per night
  1. Airbnb
  2. United States
  3. Wisconsin
  4. Sheboygan County
  5. Sheboygan