Sheboygan County holiday accommodation: holiday houses & more

Discover a selection of 209 holiday home rentals in Sheboygan County that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Stayz holiday homes have the best amenities for hanging out with the people that matter most, including pool and private pool. Prices start at AU$ 486 per night, and holiday houses and cabins are popular options for a stay in Sheboygan County. Either way, you'll find holiday accommodation for everyone's needs.

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Find the best place to stay — Sheboygan County

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Stayed Apr 2021

Best mini vacation ever and only a short drive away.

I want to thank Tom and his family for the best experience ever, they have a beautiful property with the most wonderful experience for children and adults, we arrived and our daughter couldnt believe there was small sheep eating around the cabin, we ...

Stayed Apr 2021

Beautiful Place to Unwind

My mom, sister, daughter and I spent two comfortable nights at this little gem of a cottage. We could not believe the amazing view of the lake. It was so relaxing, listening to the waves, watching the water change colors, and enjoying the fireplace. ...

Stayed Mar 2021

Comfy lake house

But The view was radically changed by a new rock sea wall along the shore. Made a mess of the lawn and side yard. Over time it will probably be cleaned up and landscape improvements made but for our stay it was a construction mess. House very comfor...

Stayed Mar 2021

Great family spot

The property was exactly as pictured and described, spotless and well-organized. Bedroom super comfy, kitchen nice and well-stocked. Right on the lake. 25 min from Kettle Moraine North Unit. Loved the huge whirlpool bathtub and wood-burning fireplace...

Stayed Mar 2021

Birthday weekend with my family

This was our first trip with my family since Covid and it definitely did not disappoint. The house was beautiful and although the weather was a bit chilly we were still able to enjoy the gorgeous Lakeview and outdoor fire pit. The hosts were wonderfu...

Stayed Mar 2021

Great location.

This was a great location and it was clean. The only issue we had was the noise. This was on top of a bar and you can hear the people as if they were inside the room. And this was in March, can’t imagine summer when they are a lot more busy and stay ...

Stayed Mar 2021

Quiet, comfortable & convenient.

We enjoyed our stay. It was a quiet location where we could relax and enjoy nature, but not far from the other things we wanted to do and see in the area. A stone's throw from beautiful Kohler/Andrea park and the lakefront. So much more comfortable a...

Stayed Mar 2021

Sandalwood Serenity

We enjoyed our 3 day stay in early March. The owners have been very thoughtful in decorating and furnishing this home. It was spotless and the kitchen well appointed. We enjoyed exploring this part of Wisconsin and the towns of Oostsburg, Sheboygan, ...

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How many holiday accommodation are available around Sheboygan County?

Our 2021 accommodation listings offer a large selection of 209 holiday rentals around Sheboygan County. From 176 holiday houses to 22 cabins, find unique holiday homes for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay around Sheboygan County is on Stayz.