Holiday houses in Sheboygan

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Popular amenities for Sheboygan holiday rentals

Stay near Sheboygan's top sights

John Michael Kohler Arts Center60 locals recommend
Il Ritrovo53 locals recommend
Trattoria Stefano44 locals recommend
Field to Fork44 locals recommend
Blackwolf Run Golf Course43 locals recommend
3 Sheeps Brewing Company42 locals recommend

Other great holiday rentals in Sheboygan

Top Guest favourite
Home in Plymouth
4.96 out of 5 average rating, 171 reviews

The 2400 sq ft Plymouth Paddock 1 hour to Lambeau

JuliaRating, 5 stars4 days ago
Can’t say enough positive things! Perfect place for families - plenty of space, well stocked, even has all the kids toys and great amount of beds / bedroom space.
Superhost
Home in Sheboygan
4.77 out of 5 average rating, 13 reviews

3 Bedroom Beach House

KatieRating, 5 stars20 months ago
Place was great! Only comment I have is the beds were too soft (I need a firmer bed) :)
Top Guest favourite
Home in Oostburg
5 out of 5 average rating, 11 reviews

SurfDaze! A Lake Michigan property

JosephRating, 5 stars1 month ago
We had an incredible stay at SurfDaze! The pictures don’t do it justice—this is a truly stunning beachfront property on Lake Michigan. The home was spotless, beautifully maintained, and exceptionally comfortable. Waking up to the sound of the waves and enjoying the breathtaking views made our trip unforgettable. We can’t wait to come back!
Top Guest favourite
Home in Glenbeulah
4.98 out of 5 average rating, 125 reviews

Stay at Sunrise LLC, Like being at Grandma's

DavidRating, 5 stars6 months ago
This place is suitable for a small family or a few adults. Very clean and well thought-out amenities made it quite attractive. Because we were very busy at Road America every day, we did not have an opportunity to use the kitchen except to make coffee, but had we wanted to cook, I'm sure we would have found everything needed. The only "warning" is that anyone with some mobility issues might find the stairway to the second floor a bit daunting. If we need a place in the area again, we would likely choose this house again.
Superhost
Apartment in Sheboygan
4.5 out of 5 average rating, 12 reviews

Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan

Christian DavidRating, 5 stars9 months ago
Excellent place, I was there for almost 2 months and is very peaceful, the place is exactly like photos, everything was great, Thank you Chris
Top Guest favourite
Home in Sheboygan
4.95 out of 5 average rating, 42 reviews

Wander Back Inn to Sheboygan

LaurieRating, 5 stars1 month ago
We had a great time at this place. Everything was as described. Very easy to work with and accommodating.
Top Guest favourite
Loft in Port Washington
4.99 out of 5 average rating, 163 reviews

Cozy Carriage House Loft – Walk to Lake & Downtown

Cathipt@Yahoo.ComRating, 5 stars5 months ago
Missy and Bret were great hosts and the treats of muffins, coffee, and drinks in the refrigerator were appreciated. This is a lovely place and a great get away. The only concern was that I misunderstood that there is only one queen bed in the bedroom. There is a second queen size pull out in the couch. The beds were comfortable and the movies, music and games are a nice addition.
Guest favourite
Home in Plymouth
4.92 out of 5 average rating, 103 reviews

Vintage Farmhouse on Blueberry Hill.

EllieRating, 5 stars2 months ago
We had a great stay. The place was exactly as described. It was convenient to town but had an amazing view. Michael was super responsive whenever we reached out. We would definitely stay here again and since we often come back to the same locations for races each year, we love to find places where we can be a repeat guest. This will definitely make the list in Plymouth.

Quick stats about holiday rentals in Sheboygan

  • Total rentals

    270 properties

  • Nightly prices starting at

    $62 AUD before taxes and fees

  • Total number of reviews

    12K reviews

  • Family-friendly rentals

    210 properties are a good fit for families

  • Pet-friendly rentals

    70 properties allow pets

  • Rentals with dedicated workspaces

    140 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Wisconsin
  4. Sheboygan County
  5. Sheboygan