Where to stay around Sheboygan?

Our 2018 property listings offer a large selection of 115 vacation rentals near Sheboygan. From 69 Houses to 23 Bungalows, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Sheboygan for a holiday or a weekend are on HomeAway.

What are the popular points of interest near where I can stay when traveling to Sheboygan?

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

  • John Michael Kohler Arts Center: 110 vacation rentals
  • Sheboygan County Historical Museum: 114 vacation rentals
  • Stefanie H. Weill Center for the Performing Arts: 111 vacation rentals
  • Whistling Straits Golf Course: 112 vacation rentals
  • Blackwolf Run: 116 vacation rentals

But there are many other points of interest around Sheboygan listed on HomeAway 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. HomeAway has 69 Houses in Sheboygan. Our other popular types of vacation rentals in Sheboygan include:

  • Bungalows: 23 rentals available
  • Cabins: 23 rentals available
  • Cottages: 23 rentals available

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

Can I find a vacation rental with pool in Sheboygan?

Yes, you can select your preferred vacation rental with pool among our 7 vacation rentals with pool available in Sheboygan. Please use our search bar to access the selection of vacation rentals available.

    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.

    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.

    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.

    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.

    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.