Sheboygan County holiday rentals

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August 2025

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Discover a selection of 224 homes, 65 apartments and other holiday rentals in Sheboygan County that are perfect for your trip. Whether you’re staying in a holiday home with friends, family or even just your pets, you'll have the amenities that you expect and more, which might include parking and a hot tub. At the end of the day, you'll be able to choose a property to rent to meet everyone's needs, including accessible or non-smoking choices.

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Find the best place to stay - Sheboygan County

Seagull Beach Guest House, Unique Lake Michigan Cottage on private beach

Sleeps 2 · 1 bedroom · 2 bathrooms

Classy? Yes, but comfy, too! Enjoy yesteryear's elegance with modern perks.

Labor Day will be here before you know it. Celebrate with your favorite group!

Sleeps 24 · 10 bedrooms · 6+ bathrooms

The private, beautiful 2 acre lakeside lot is surrounded by forest.

Large Unique & Artistic Lake Michigan Beach House / Awesome Game Room

Sleeps 14 · 4 bedrooms · 3+ bathrooms

Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!

Sleeps 6 · 2 bedrooms · 1+ bathroom

Choose a holiday rental for your Sheboygan County getaway

Learn about the unique charm of Sheboygan County with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in and around Sheboygan County

Are you hoping to find things to do during your stay? Venture out of your holiday home and experience everything that Sheboygan County has to offer. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

Blue Harbor Resort & Conference Center Water Park (0.5 mi / 0.8 km)
Blackwolf Run (3.4 mi / 5.5 km)
The Bull at Pinehurst Farms Golf Course (5.6 mi / 9 km)
Whistling Straits Golf Course (7 mi / 11.3 km)
Road America (14.1 mi / 22.8 km)
Port Washington Ghost Walk (26.2 mi / 42.2 km)

Exploring the natural landscape of Sheboygan County

Whether you're looking for adventure or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in Sheboygan County. These are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

Bookworm Gardens (2.1 mi / 3.4 km)
Kohler Park Dunes State Natural Area (5.9 mi / 9.5 km)
North Beach (17.9 mi / 28.7 km)
South Beach (18.8 mi / 30.2 km)
Wilke Lake (19.4 mi / 31.3 km)
Kettle Moraine Lake (25.7 mi / 41.3 km)

Frequently asked questions

What is the best area to stay in Sheboygan County when booking a holiday home?

If your itinerary includes Sheboygan County, Sheboygan is regarded as one of the most sought-after areas to spend a getaway. While here, keep busy by exploring fantastic attractions like Blue Harbour Resort & Conference Centre Water Park and Kettle Moraine State Forest.

What is the most popular type of holiday home accommodation in Sheboygan County?

Houses are the most popular kind of holiday home in Sheboygan County, according to our data. Even if you have something a little different in mind, Stayz has properties in all shapes and sizes. Explore our options to find your perfect Sheboygan County pad.

How much does it cost to rent a holiday home in Sheboygan County?

A number of factors can influence what you'll pay for your holiday home in Sheboygan County, like the time of year, length of stay and property type. However, all our holiday homes have something in common — incredible value. Just enter your travel dates to find your ideal escape.

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

The average price for a holiday home close to the beach in Sheboygan County depends on when you're visiting the area and the type and size of property you're searching for. You can find prices easily and quickly on Stayz by entering your preferred travel dates. Then use our handy filter tool to choose the number of bedrooms and amenities important to you, such as air conditioning, WiFi and a pool.

What are popular home amenities in Sheboygan County?

A washing machine, a fridge and a microwave oven are rated the most popular home amenities in Sheboygan County. Whether you're taking a trip alone, with your better half or a group of dear friends, Stayz will help you find a holiday home that fits your tastes with all the features you need.

Are there large group holiday homes in Sheboygan County?

Sheboygan County has 57 holiday homes that can cater to 10 or more people. These stays come with the privacy and space you need to enjoy good times with friends and family.

What are the top attractions for families in Sheboygan County?

Keep your kids entertained at these fantastic family-friendly attractions in Sheboygan County:

Sheboygan County Fairgrounds
Whistling Straits Golf Course
Blue Harbour Resort & Conference Centre Water Park

Can I find two-bedroom holiday homes in Sheboygan County?

You can pick from 61 two-bedroom homes in Sheboygan County. Give your little ones the second room or maybe fill it with a couple of your best buddies. There's a comfy spot for whoever's lucky enough to come along for the ride.

Are there holiday homes with WiFi in Sheboygan County?

Sheboygan County has 131 holiday homes with WiFi, so you can stay connected when you're away. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming TV shows with the family to updating your social media, these Stayz homes make it a cinch to get online.

How old do you have to be to rent a holiday home in Sheboygan County?

It's a good idea to check with the Sheboygan County holiday property you're looking at on Stayz as age restrictions differ. However, generally it's 16, 18 or 21.

How long can I rent a holiday home in Sheboygan County for?

It all depends on the Sheboygan County property. To see a list of options offering extended stays, simply enter your dates and number of guests into the Stayz search page. Enjoy having the property to yourself, as well as comforts such as a full kitchen, air conditioning and outdoor spaces where the little ones can play. Keep your eyes peeled for long-term stays that offer discounted weekly or monthly prices.