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Holiday rentals in Sheboygan

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Top-rated holiday rentals in Sheboygan

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

Sophisticated  Manor for the Holidays
SUPERHOST
Entire residential home · 8 guests · 4 beds · 4 bathrooms
Sophisticated Manor for the HolidaysThis home was built for entertaining and what better time to do so than the Holiday season! Modern & Timeless Chic. Enjoy the expansive 4,500 square feet of elegance and character that adorns this well-appointed home. Complete with 3 bedrooms, 3 full baths and 2 half baths, a den with a queen sleeper sofa, & many different areas for entertainment throughout. Situated between the lakefront and downtown. Just a short drive to Whistling Straights and within an hour of Milwaukee and Green Bay.
Dog Friendly Blue Door Cottage
SUPERHOST
Entire residential home · 6 guests · 4 beds · 1 bathroom
Dog Friendly Blue Door CottageNobody should have to leave their fur baby behind while on vacation. This is exactly why we created this comfortable home with your family & puppy in mind. You'll be at ease knowing that your pooch will be having just as much fun as you are. Modern hints are complemented by the cozy, welcoming decor found throughout. The coffee bar is a fav for any morning person, and the "take-a-wine leave-a-wine" wine bar offers evening excitement! The huge yard features a fire pit, gas grill, & cornhole.
River Home Getaway with River Access
SUPERHOST
Entire residential home · 8 guests · 4 beds · 2 bathrooms
River Home Getaway with River AccessEnjoy 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.

Holiday rentals for every style

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Popular amenities for Sheboygan holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Sheboygan

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2BR Main Floor Beach/Lake Condo *NO EXTRA FEES*
SUPERHOST
No reviews yet
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Sheboygan Marina 2br Upper-Near beach / downtown
SUPERHOST
  1. Entire residential home
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The Kohler House
SUPERHOST
  1. Entire apartment
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Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home
SUPERHOST
  1. Entire rental unit
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Downtown Walk-up
  1. Private room
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Farm-Stay B&B - The Olive Suite
SUPERHOST
  1. Entire rental unit
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Heart of Downtown Sheboygan
SUPERHOST
  1. Entire villa
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Just steps from the shore of Lake Michigan
  1. Entire loft
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Wis. Get-away, spacious/stylish 2br loft, parking
  1. Entire rental unit
  2. Sheboygan
Entire Upper Rental Unit-South Central Sheboygan
SUPERHOST
  1. Entire rental unit
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Cozy Sheboygan Upper
SUPERHOST
  1. Entire cottage
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Bright Antique Cottage