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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
The Beach | Sheboygan 2Br/1 Ba
Welcome to the Beach, a lakeside retreat in the heart of Sheboygan. Located just 3 blocks from Lake Michigan and a stones throw to down town Sheboygan, The Beach is the perfect place to center your visit to Eastern Wisconsin. The Beach is the main floor unit of a duplex featuring 2 bedrooms, 1 bathroom, a well stocked kitchen, a cozy living room, fast wifi and convenient amenities. We have an easy check out with no to-do lists. Just pack and go!
$115 per night
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Rental unit in Sheboygan
Sheboygan Surf House "Jetties"
Located just 24 steps above Wisconsin's first Surf Shop, EOS Surf. Our Urban living oasis is a fully equipped studio apartment conveniently located in the heart of downtown, just steps from bars and restaurants and only blocks to Lake Michigan South Pier and Blue Harbor. Whether you are here for adventure sports like Surfing on the Great Lake, Kite boarding, charter fishing, a Wedding or leisure time SSH is perfect for you. Support Dog friendly
$54 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!
$78 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 Black Pig
Black Pig19 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
$176 per night
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Cabin in Oostburg
Cabin w/ Seasonal Hot Tub Lake Michigan/State Park
$341 per night
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Cabin in Elkhart Lake
The LODGE in Elkhart Lake
$181 per night
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Cabin in Cascade
Willows Cabin Cascade, On Lake
$675 per night
Cabin in Random Lake
The Random Cabin (On Random Lake)
$145 per night
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Cabin in Plymouth
Little Lake Cabin - Road America Enthusiasts!
$198 per night
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Cabin in Elkhart Lake
The Cabin of Elkhart Lake
$288 per night
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Cabin in Valders
Cozy cabin in the woods
$325 per night
Cabin in Valders
Valders Log Cabin near EEA Air Show & Sheboygan!
$371 per night
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Cabin in Plymouth
Cabin moments away from Road America and Lakes
$175 per night
Cabin in Plymouth
The Cottage at Crystal Lake
$325 per night
Cabin in Cascade
This is the place! Lakefront cabin for big family
$638 per night

Stays in Business Drive North

Home in Sheboygan
Guest House, Spacious one bedroom, close to lake`
$85 per night
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Vacation home in Sheboygan
Lovely modern two bedroom home with fire pit
$133 per night
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Condo in Sheboygan
Beachside Lake View - 2br - First Floor - Garage
$121 per night
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Condo in Sheboygan
2BR Lake View Condo-2nd floor
$157 per night
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Stays in James Madison

Rental unit in Kohler
Washington Walk Historic House w/elegant spa bath
$162 per night
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Rental unit in Sheboygan
The Garden | Sheboygan 2 Br/1Ba, Pet Friendly
$114 per night
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Rental unit in Sheboygan Falls
Cozy comfortable hideaway
$86 per night
Home in Sheboygan
Top Floor Condo - Lake Michigan View Retreat
$174 per night
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Stays in End Park

Home in Sheboygan
Winter Romantic Getaway Boutique Home W/ Fireplace
$133 per night
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Guest suite in Sheboygan
Upper Duplex near Lake Michigan
$62 per night
Private room in Sheboygan
Room 3:Charming shabby chic bedroom with queen bed
$40 per night
Condo in Sheboygan
Urban Townhouse
$117 per night
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