Discover a selection of 166 vacation rentals in Sheboygan, WI that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $125 per night, and houses and cabins are popular options for a stay in Sheboygan. Either way, you'll find a rental for everyone's needs.
Destination guide

We don't say this lightly: it's the 'wurst!

This little town resting on the shores of Lake Michigan has plenty of culture, festivals and events, but locals are proudest of Sheboygan's true claim to fame – it's the Bratwurst Capital of the World. Sheboygan has been flaunting this title for almost 50 years, and locals have very strong opinions on how brats should be made. Even if your Sheboygan vacation rental comes with a grill, it might be best to leave this one to the experts. Be sure to hit up one of the many local establishments working for bragging rights to Best Brats.

Things to do

A tiny little town, packed to the brim with history

Sheboygan's downtown offers a few museums, all highlighting the city's culture and history. Catch a performance or a local artist's latest exhibit at the arts center, or head to the Sheboygan County Historical Museum for some historical context. Families will love the acclaimed children's museum, and each place offers a unique perspective on the surrounding region. For travelers looking to feel a little bit more active, there are plenty of parks ripe for exploring, plus an indoor water park and a children's space-themed interactive science museum.


From brats to boats, with a bit of culture in between

While bratwurst is the local fave, it's not all Sheboygan has to offer. Small-town charm is around every corner, with annual events including a County Fair in summer and a local Oktoberfest every fall. There are concerts, festivals, and art shows in between, plus a handful of museums for travelers interested in learning more about the local culture and history. The lake is a huge draw for summer travelers, with a variety of tour companies offering fishing charters and boat tours. Each summer, too, the largest lake-surfing competition in the world comes to town.


Winter is coming... pretty much all year long

Technically, Sheboygan has 4 seasons. But true Wisconsinites know that summer never lasts long enough, and winters can be so brutal that they don't leave your memory easily. Ice fishing fanatics might disagree, but the best time to visit Sheboygan is in the spring or summer, when you can enjoy the slightly higher temps. July and August are the warmest, and you may even be able to dip your toes in Lake Michigan. January and February are Sheboygan's coldest months by far, so pack an extra layer or 12 for your Sheboygan vacation rental.

Natural features

Grab a brat and a beer, and look toward the lake

Sheboygan's position on Lake Michigan is certainly its most attractive feature, with a bustling harborfront perfect for sitting outside and enjoying a brat – weather permitting, of course. It's best to look closest to the lake when searching for a Sheboygan vacation rental, because no matter the time of year, this expansive glittering gem is definitely the heartbeat of the city. Fishing is the sport of choice year round, but in summer, the banks turn into proper beaches. Join the locals in the sand, and enjoy the momentary break from frigid winter temps.

How many vacation rentals are available around Sheboygan, WI?

Our 2020 property listings offer a large selection of 166 vacation rentals around Sheboygan. From 138 house rentals to 19 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What are the popular point of interests near where I can stay when traveling to Sheboygan?

Vrbo offers a large selection of vacation rentals near lovely places in Sheboygan. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Sheboygan County Historical Museum: 164 vacation rentals
  • University of Wisconsin-Sheboygan: 163 vacation rentals
  • John Michael Kohler Arts Center: 160 vacation rentals
  • Stefanie H. Weill Center for the Performing Arts: 161 vacation rentals
  • Blue Harbor Resort & Conference Center Water Park: 161 vacation rentals

But there are many other points of interest around Sheboygan listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Sheboygan?

Yes, of course. Vrbo has 138 Houses in Sheboygan. Our other popular types of vacation rentals in Sheboygan include:

  • Cabins: 19 rentals available
  • Cottages: 19 rentals available
  • Condos/Apartments: 17 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Bungalows and more.

Can I find a vacation rental with pool in Sheboygan?

Yes, you can select your preferred vacation rental with pool among our 5 vacation rentals with pool available in Sheboygan. Please use our search bar to access the selection of vacation rentals available.

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