Sheboygan holiday homes

We found 427 holiday rentals — enter your dates for availability
Select from 97 houses, 26 flats and other holiday rentals to find the perfect place for your stay in Sheboygan. Whether you're going on holiday with family or friends, holiday rentals have the best amenities for hanging out with the people that matter most, such as Wi-Fi and cable TV. You'll be sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Sheboygan

Showing deals for:30 Oct - 6 Nov

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Why visit Sheboygan

  • Beautiful parks and outdoor spaces: Sheboygan features stunning urban parks perfect for leisurely strolls and outdoor activities.
  • Cultural attractions: Explore local museums and art spaces showcasing the city's vibrant creative scene.
  • Scenic waterfront: Enjoy breathtaking views along Sheboygan's picturesque lakeshore, ideal for relaxation.
  • Family-friendly activities: The city offers a variety of engaging activities suitable for visitors of all ages.
  • Charming downtown area: Discover unique shops and eateries while immersing yourself in the local vibe.

Top attractions in and around Sheboygan

Sheboygan offers an engaging mix of outdoor adventures and cultural experiences, perfect for a romantic getaway or family holiday. Visitors can explore its urban parks, museums, and art spaces, enjoying a blend of natural beauty and creative intrigue. The city caters to those seeking both a leisurely and active break, with opportunities for memorable outdoor pursuits and captivating local art scenes.

  • John Michael Kohler Arts Center: This vibrant art museum showcases contemporary art and features engaging exhibitions, performances, and community events. Its unique architecture and commitment to cultural experiences make it a must-visit for art enthusiasts.
  • Kohler Design Center: Just a short drive from Sheboygan, this museum highlights innovative designs and products from the Kohler Company. Visitors can explore inspiring displays of bathroom and kitchen designs that blend functionality and artistry.
  • Sheboygan South Pier: A scenic spot for leisurely strolls, fishing, and stunning views of Lake Michigan, the South Pier offers a relaxing atmosphere and picturesque sunsets, perfect for unwinding after a day of exploration.

Things to do recommended for couples

Sheboygan offers a charming getaway for couples. Enjoy a sunset stroll along the picturesque Lake Michigan shoreline, indulge in a romantic dinner at a lakeside restaurant, or explore the local art scene together. Don’t miss a visit to the serene Kohler-Andrae State Park for a peaceful escape.

Things to do recommended for families

Families in Sheboygan can enjoy exciting days at local parks and interactive museums, perfect for children with engaging, hands-on exhibits and plenty of outdoor adventures to explore.

Things to do recommended for groups

Groups visiting Sheboygan can embark on a scenic drive along Lake Michigan’s shoreline, explore local craft breweries and enjoy a leisurely stroll through the historic downtown, experiencing local culture and hospitality.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Sheboygan

Whether you're journeying with mates, travelling as a family, with your furry companions, or seeking extended stays, remember to use the appropriate filters. Here are some Vrbo booking tips for you.

  • Traveling to Sheboygan with a group: Consider the number of bedrooms required, along with amenities like a full kitchen or outdoor space for group gatherings. Thankfully, you can filter for all these features and more on Vrbo.
  • Traveling to Sheboygan with young kids: Traveling with little ones can present its challenges. It’s important to prioritise their comfort and safety, ensuring there are amenities suited to their age – like a private pool – and to think about how close you are to attractions that are family-friendly.
  • Taking your pets with you to Sheboygan: For many, a family holiday isn’t complete without their furry companion by their side. If that resonates with you, then explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds so that everyone can feel at home.
  • Planning for a long term stay visiting Sheboygan: If you're seeking holiday accommodations with special rates for extended stays, you've come to the right spot. With the appropriate filter, you can easily discover and save on monthly rentals. You might also want to include options like a parking bay, a well-equipped kitchen, or a private pool in your search.

Where to stay in and around Sheboygan

Discover Sheboygan, Wisconsin – a charming city offering a blend of family-friendly and romantic experiences. Stroll through downtown Sheboygan, marvel at stunning views, and enjoy the idyllic holiday destination vibe. From scenic Sheboygan County to the relaxing allure of local neighbourhoods, there's an abundance of outdoor and cultural attractions to explore. Experience the diverse charm that makes Sheboygan a perfect getaway for families and couples alike.

  • Sheboygan Falls: Situated 8km from Sheboygan, Sheboygan Falls is a charming city celebrated for its scenic beauty and outdoor activities. This area is perfect for those seeking a romantic getaway or a relaxing day in nature. You can explore its lovely recreational areas, play a round of golf, or enjoy the stunning views of the nearby lake and beach. The local racetrack adds a touch of excitement for motorsport enthusiasts, making it a well-rounded destination for all types of travellers.
  • Haven: Nestled in the vicinity of Sheboygan, Haven is a delightful village that caters to families and sports enthusiasts alike. With its inviting urban parks and beautiful beaches, it’s an excellent spot for outdoor activities. Golfing here is a popular pastime, and there are plenty of educational opportunities for families to engage in. Haven’s proximity to the lake allows for various water-based activities, ensuring a fun-filled experience for visitors of all ages.
  • Cleveland: Located 19km from Sheboygan, Cleveland is a picturesque city that attracts those looking for outdoor adventures and scenic landscapes. Ideal for romantic escapes, Cleveland offers beautiful golf courses, extensive recreational areas, and access to the nearby national state park. The stunning beach along the lake provides a perfect backdrop for relaxation and leisure activities. Whether you’re hiking in the park or enjoying a leisurely day by the water, Cleveland is a fantastic addition to your travel itinerary.

Best time to go to Sheboygan

If you're planning a trip to Sheboygan, it's a good idea to check both the weather and property rates. The warmest months are July and August.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January22.6°F (-5.2°C)No Rain (Dry)Mostly Cloudy
February22.8°F (-5.1°C)No Rain (Dry)Mostly Cloudy
March32.7°F (0.4°C)Light RainMostly Cloudy
April40.8°F (4.9°C)Light RainMostly Cloudy
May51.4°F (10.8°C)Light RainMostly Sunny
June62.2°F (16.8°C)Light RainMostly Sunny
July70.0°F (21.1°C)Light RainMostly Sunny
August70.0°F (21.1°C)Light RainMostly Sunny
September63.9°F (17.7°C)Light RainMostly Sunny
October52.0°F (11.1°C)Light RainMostly Sunny
November39.9°F (4.4°C)Light RainMostly Sunny
December30.0°F (-1.1°C)Light RainMostly Cloudy

Booking with Vrbo is simple

Are you aiming to save on your upcoming adventure? Being flexible with your travel dates can make a real difference, as prices often fluctuate. Additionally, booking a longer stay can lead to considerable savings. To discover a Vrbo property that suits your budget, feel free to use our filters to sort by price, location, and type of holiday accommodation. We're here to help you find the perfect spot for your getaway.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a dedicated area where you can start planning new adventures, pick up where you left off, or manage your current bookings. Your saved or booked properties are neatly categorised into Potential, Upcoming, or Current Trips. For more details and to explore the Trip Boards, please visit: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Explore the waterfront setting in Sheboygan

The area's museums and art galleries are just some of the reasons to come on holiday to 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 hoping to find attractions to visit while you're in the area? Venture out of your holiday home and check out everything that makes Sheboygan a one-of-a-kind holiday spot. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Blue Harbor Resort & Conference Center Water Park (0.4 mi / 0.6 km)
  • Blackwolf Run (3.5 mi / 5.6 km)
  • The Bull at Pinehurst Farms Golf Course (5.7 mi / 9.1 km)
  • Whistling Straits Golf Course (7.1 mi / 11.4 km)
  • Road America (14.2 mi / 22.9 km)
  • Evergreen Golf Course (12.3 mi / 19.8 km)

Exploring the beaches and other natural features in Sheboygan

Travellers enjoy Sheboygan for its lakeside setting and riverfront. Whether you're an outdoor enthusiast or just want to appreciate the scenery, Sheboygan is a great place to get outside. These are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • North Side Municipal Beach (0.6 mi / 1 km)
  • Kohler Park Dunes State Natural Area (5.8 mi / 9.4 km)
  • Bookworm Gardens (2.2 mi / 3.5 km)
  • Sheboygan Indian Mound Park (3.7 mi / 6 km)
  • Dairyland Park (11.8 mi / 19 km)
  • Rhine Center Bog State Natural Area (14.2 mi / 22.9 km)

Seasonal weather averages in Sheboygan

If you're planning a holiday around the weather, August, July, September and June are the hottest months to visit, when temperatures average 19°C.

Frequently asked questions

What is the best area to stay in Sheboygan when booking a holiday home?
Ellis Historical District is among the more sought-after locations for a holiday 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 holiday home accommodation in Sheboygan?
Condos are the most popular style of holiday home in Sheboygan, according to our data. Even if you have something else in mind, Bookabach has holiday homes in many shapes and sizes. Browse our many options to find your perfect fit.
How much does it cost to rent a holiday home in Sheboygan?
A range of things influence what you'll pay for your holiday home in Sheboygan, such as the season, length of stay and type of property. Still, all of our holiday 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 Bookabach. 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 holiday homes in Sheboygan?
With 42 properties that allow pets, your happy hound can also come along on your Sheboygan holiday. Use the filter tool to search our pet-friendly holiday homes and find a stay that's pawfect on Bookabach.
What are popular home amenities in Sheboygan?
A water view, a lake view and tennis are the most popular home amenities in Sheboygan. Whether you're taking a trip by yourself, with your significant other or as a family group, Bookabach will help you find a holiday home that matches your style with all the conveniences you're looking for.
Are there large group holiday homes in Sheboygan?
Sheboygan has two holiday homes 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 holiday homes in Sheboygan that welcome kids?
With 42 family-friendly holiday 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 holidaying 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 holiday is child's play with these awesome family-friendly attractions:

  • Blue Harbour Resort & Conference Centre Water Park
  • Sheboygan County Historical Museum
  • Childrens Museum

Can I find two-bedroom holiday homes in Sheboygan?
Gather your loved ones and enjoy a relaxing escape in one of the 15 two-bedroom holiday homes Sheboygan has to offer.
Are there holiday homes with WiFi in Sheboygan?
Pick from 20 holiday homes 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 Bookabach.
How can I find holiday homes with air conditioning in Sheboygan?
There are 42 Bookabach holiday 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.
How old do you have to be to rent a holiday home in Sheboygan?
The minimum required age is generally 16, 18 or 21. It can change between properties on Bookabach, so look at the rules of your preferred Sheboygan holiday home before you book.
How long can I rent a holiday home in Sheboygan for?
The amount of time you can stay in a Sheboygan holiday home for is down to the property. Simply enter your dates of travel to browse available options offering extended stays. They have all you require to make your extended trip more convenient and enjoyable, like air conditioning and kitchens. Some Bookabach holiday homes may also offer weekly or monthly discounted prices, so you can stay longer for less money.