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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.

SUPERHOST
  1. Entire rental unit
  2. Sheboygan
Sheboygan Surf House "Jetties"

Located just 24 steps above Wisconsin's first Surf Shop, EOS Surf. Our newly remodeled 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 or leisure time SSH is perfect for you.

$56 per night
SUPERHOST
  1. Entire rental unit
  2. 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.

$65 per night
SUPERHOST
  1. Entire rental unit
  2. Sheboygan
Cozy Sheboygan Upper

Located in the Historic Ellis Neighborhood two blocks from the beach, this 1870's home is waiting for your visit to Sheboygan. You will have easy access to downtown, the lakefront and the river boardwalk all within four blocks.

$73 per night

Vacation rentals for every style

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Cabin rentals in Sheboygan

  1. Entire cabin
  2. Oostburg
"Pine Dunes Cabin" near Kohler and Lake Michigan.
$343 per night
  1. Entire cabin
  2. Plymouth
Little Lake Cabin - Road America Enthusiasts!
$175 per night
  1. Entire cabin
  2. Plymouth
The Cottage at Crystal Lake
$325 per night
  1. Entire cabin
  2. Cascade
Lakefront Rural Cabin On Private Lake Community
$414 per night
  1. Entire cabin
  2. Manitowoc
Rustic cabin on shoreline of Lake Michigan
$350 per night
  1. Entire cabin
  2. Valders
Valders Log Cabin near EEA Air Show & Sheboygan!
$316 per night
SUPERHOST
  1. Entire cabin
  2. Two Rivers
All Natural Aquamarine Cottage
$111 per night
  1. Entire cabin
  2. Plymouth
Cabin moments away from Road America and Lakes
$175 per night
  1. Entire cabin
  2. Valders
Cozy cabin in the woods
$325 per night
SUPERHOST
  1. Entire cabin
  2. Cascade
Willows Cabin Cascade, On Lake
$575 per night
SUPERHOST
  1. Entire cabin
  2. New Holstein
Big Buck Lodge - Large and Small Groups Welcome!
$219 per night
  1. Entire cabin
  2. Cascade
Newly renovated! Large luxury lakefront Cabin
$705 per night