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Sheboygan vacation rentals

We found 362 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Select from 93 houses, 36 condos, and other vacation rentals to find the perfect place for your stay in Sheboygan. Whether you're traveling with family, friends, or just your furry companion, vacation rentals have the amenities you expect for your stay, which might include cable TV and a washer and dryer. You'll be sure to find a rental for everyone's needs, including places that are non-smoking or accessible.

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Explore the waterfront setting in Sheboygan

The area's museums and art galleries are just a few of the reasons to vacation in Sheboygan. Renowned for its lake, beaches and restaurants, this city welcomes all visitors. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Sightseeing in and around Sheboygan

Are you looking for attractions to visit during your stay? Venture out of your vacation home and check out everything that Sheboygan has to offer. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Blue Harbor Resort & Conference Center Water Park (0.4 mi / 0.6 km)
  • Blackwolf Run (3.5 mi / 5.6 km)
  • Whistling Straits Golf Course (7.1 mi / 11.4 km)
  • Road America (14.2 mi / 22.9 km)
  • The Bull at Pinehurst Farms Golf Course (5.7 mi / 9.1 km)
  • Evans (5.2 mi / 8.3 km)

Exploring the beaches and other natural features in Sheboygan

Travelers enjoy Sheboygan for its lakeside setting and riverfront. Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Sheboygan is a great place to get outside. Here are some of the area’s noteworthy features, all within 30 miles (48.2 km) of the city center:

  • Kohler-Andrae State Park (6.7 mi / 10.7 km)
  • Harrington Beach State Park (18 mi / 29 km)
  • Kettle Moraine State Forest (22.4 mi / 36.1 km)
  • North Beach (17.8 mi / 28.7 km)
  • North Side Municipal Beach (0.6 mi / 1 km)
  • Bookworm Gardens (2.2 mi / 3.5 km)

Seasonal weather averages in Sheboygan

If you're planning a vacation around the weather, August, July, September and June are the hottest months to visit, when temperatures average 67°F.

Frequently asked questions

What is the best area to stay in Sheboygan when booking a vacation rental?

Ellis Historical District is among the more sought-after locations for a vacation home in Sheboygan. Spend your getaway here to enjoy all the convenience and privacy that comes with having a place to yourself.

What is the most popular type of vacation rental accommodation in Sheboygan?

Condos are the most popular style of vacation rental in Sheboygan, according to our data. Even if you have something else in mind, Vrbo has vacation homes in many shapes and sizes. Browse our many options to find your perfect fit.

How much does it cost to rent a vacation rental in Sheboygan?

A range of things influence what you'll pay for your vacation rental in Sheboygan, such as the season, length of stay and type of property. Still, all of our vacation homes have something in common — exceptional value. Simply add your travel dates to find your ideal fit.

How much does it cost to rent a beach house in Sheboygan?

When you travel and the size and style of the property will help determine the cost of your beachside stay. Type in your Sheboygan travel dates to see all your options on Vrbo. Looking for basics like WiFi, or perks like a private pool? Use the filters to select the features and amenities you want.

Are there pet-friendly vacation rentals in Sheboygan?

With 42 properties that allow pets, your happy hound can also come along on your Sheboygan vacation. Use the filter tool to search our pet-friendly vacation rentals and find a stay that's pawfect on Vrbo.

What are popular rental amenities in Sheboygan?

A water view, a lake view and tennis are the most popular rental amenities in Sheboygan. Whether you're taking a trip by yourself, with your significant other or as a family group, Vrbo will help you find a vacation home that matches your style with all the conveniences you're looking for.

Are there large group vacation rentals in Sheboygan?

Sheboygan has two vacation rentals that can fit 10 or more people. These stays come with the privacy and space you need to enjoy good times with your nearest and dearest.

Are there vacation rentals in Sheboygan that welcome kids?

With 42 family-friendly vacation properties to select from in Sheboygan, now is a superb time to introduce your little ones to the excitement of travel. Check our "Properties good for families" filter box to look for stays that feature amenities ideal for vacationing families, like full kitchens, outdoor spaces, entertainment areas and bunk beds.

What are the top attractions for families in Sheboygan?

Keeping the kids happy during your Sheboygan vacation is child's play with these awesome family-friendly attractions:

  • Blue Harbor Resort & Conference Center Water Park
  • Sheboygan County Historical Museum
  • Childrens Museum

Can I find two-bedroom vacation rentals in Sheboygan?

Gather your loved ones and enjoy a relaxing escape in one of the 15 two-bedroom vacation rentals Sheboygan has to offer.

Are there vacation rentals with WiFi in Sheboygan?

Pick from 20 vacation rentals with WiFi in Sheboygan. If you want to disconnect from daily life on your trip, but still need to be connected to the web, these properties are just what you need. Narrow your search by applying the WiFi filter on Vrbo.

How can I find vacation rentals with air conditioning in Sheboygan?

There are 42 Vrbo vacation homes with air conditioning in Sheboygan providing that cooling breeze and extra comfort level. Simply enter your travel dates and then use our filter tool to help you find properties with air conditioning.

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