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Sheboygan vacation rentals

We found 388 vacation rentals — enter your dates for availability

Select from 91 houses, 27 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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Find out more about Sheboygan

Find out more about Sheboygan

Why visit Sheboygan

  1. Beautiful Beaches: Sheboygan boasts stunning beachfronts perfect for sunbathing and water activities.
  2. Outdoor Adventures: Enjoy hiking and exploring national and state parks that showcase the area's natural beauty.
  3. Cultural Experiences: Discover historic houses and local art that reflect Sheboygan's rich history and vibrant culture.
  4. Cozy Accommodations: Choose from a variety of vacation rentals, including charming log cabins and convenient motels.
  5. Friendly Locals: Experience the warmth and hospitality of Sheboygan’s welcoming community.

Popular types of accommodation in Sheboygan

Planning a getaway to Sheboygan? You're in for a treat! This charming city offers a variety of vacation rentals, including private homes, cozy apartments, and inviting caravan parks. Whether you’re looking for a comfortable motel or a rustic log cabin, Sheboygan has accommodations to suit every traveler’s needs. Explore popular amenities and find the perfect rental unit to make your stay unforgettable!

  • Houses: The top choice for travelers in Sheboygan, offering spacious accommodations ideal for families or groups.
  • Apartments: A popular option for those seeking a cozy and convenient stay in the heart of the city.
  • Caravan Parks: Perfect for outdoor enthusiasts, these parks provide a unique and adventurous lodging experience.
  • Condos: A great pick for visitors wanting modern amenities and a home-like atmosphere.
  • Cottages: Charming and quaint, these rentals offer a peaceful retreat near nature.**

Top attractions in Sheboygan

Sheboygan, Wisconsin, offers a delightful mix of outdoor activities, scenic views, and romantic spots perfect for a vacation. Visitors can explore national and state parks, historic houses, and beautiful beaches, catering to those seeking cultural experiences and family fun. For a more extended adventure, consider exploring Manitowoc and enjoying a relaxing lakefront vacation to fully embrace the area's charm.

  1. John Michael Kohler Arts Center: This vibrant art museum in Sheboygan features an impressive collection of contemporary art and unique exhibitions, immersing visitors in the local culture and creativity.
  2. Kohler Design Center: Located 3 miles from Sheboygan, this museum showcases innovative design and craftsmanship, particularly in kitchen and bath products, reflecting the rich heritage of the Kohler Company.
  3. North Side Municipal Beach: Just 0.6 miles from Sheboygan, this lovely beach offers sandy shores for sunbathing, swimming, and beach activities, perfect for a relaxing day by Lake Michigan.

Things to do recommended for couples

If you're seeking a romantic getaway in Sheboygan, consider dining at Antoinette, a charming restaurant located 13 miles away. With its cozy ambiance, it's perfect for couples looking to enjoy a delightful meal together and create lasting memories in a beautiful setting.

Things to do recommended for families

Families will have a blast at the Blue Harbor Resort & Conference Center Water Park, enjoying exciting water slides and pools. For a relaxing day, head to Kohler-Andrae State Park, where you can unwind amidst nature just 7 miles from Sheboygan.

Things to do recommended for groups

Group travelers in Sheboygan can enjoy a round of golf at the stunning Whistling Straits Golf Course, experience the culture and entertainment at the Stefanie H. Weill Center for the Performing Arts, and browse unique finds at Evans, located 5 miles away from the city.

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

If you're traveling with a group, family, or pets, or if you're interested in longer stays, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Sheboygan with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and much more on Vrbo.
  • Traveling to Sheboygan with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with ensuring access to suitable amenities like a private swimming pool. Additionally, think about how close you are to family-friendly attractions.
  • Taking your pets with you to Sheboygan: For many families, a vacation isn't truly enjoyable without their furry companion by their side. If this resonates with you, take a look at Vrbo listings that welcome pets. Most of these pet-friendly properties come equipped with feeding bowls and cozy beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Sheboygan: If you're in search of vacation rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Sheboygan

Sheboygan, Wisconsin, offers a charming blend of outdoor adventures and scenic beauty, making it an ideal destination for a romantic getaway or family-friendly vacation. Explore the stunning beachfront, enjoy the vibrant springtime blooms, and unwind in cozy retreats. With friendly locals and picturesque surroundings, Sheboygan promises a memorable experience filled with excursions and art. Discover the best locations to soak in the Midwestern charm and create lasting memories during your visit.

  • Kohler: Located a mere 4 miles from Sheboygan, Kohler is a charming village renowned for its stunning outdoor scenery and adventurous spirit. Visitors can enjoy a variety of activities, including golfing at the world-class Kohler golf courses and exploring the picturesque recreational areas. Nature enthusiasts will appreciate the proximity to beautiful lakes, sandy beaches, and the serene landscapes of nearby national parks. Kohler is perfect for those seeking a blend of relaxation and outdoor exploration.
  • Manitowoc: Situated 24 miles from Sheboygan, Manitowoc is a delightful city that offers a romantic and scenic getaway. The area invites travelers to partake in outdoor activities such as golfing and enjoying the lush recreational spaces. Notable attractions include the stunning lakeside views, an engaging stadium, and the scenic national state park nearby. Manitowoc’s charming waterfront and vibrant downtown make it an ideal destination for couples and families looking to unwind and explore.
  • Elkhart Lake: Just 16 miles from Sheboygan, Elkhart Lake is a picturesque destination known for its outdoor adventures and romantic ambiance. Visitors can indulge in various activities, including exploring the local recreational areas and enjoying a fun-filled day at the water park. The city is surrounded by breathtaking lakes and features a famous racetrack, perfect for motorsport enthusiasts. Its proximity to national state parks provides ample opportunities for hiking and nature walks, making Elkhart Lake a must-visit for outdoor lovers.

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. Peak season runs from June to August, while off-peak times, like December to February tend to have fewer bookings and better deals.

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

Booking with Vrbo is simple

Are you hoping to cut costs on your upcoming journey? One effective strategy is to remain flexible with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often results in substantial savings. To discover the perfect Vrbo rental that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Save more with One Key

When you reserve a qualifying Vrbo for your group getaway, you'll receive OneKeyCash™ on the entire reservation. Being the organizer truly has its advantages! Become a member of our One Key rewards program to unlock exclusive savings and earn OneKeyCash™ on eligible stays. Sign up today and begin enjoying the benefits!

Vrbo Trips: Effortless planning

Vrbo’s Trip Board is designed to help you plan your travel seamlessly. It provides a convenient area for you to create new trips, manage your existing plans, or review your bookings. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To start exploring Trip Boards, please visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

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)
  • 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

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:

  • Bookworm Gardens (2.2 mi / 3.5 km)
  • North Beach (17.8 mi / 28.7 km)
  • South Beach (18.7 mi / 30.1 km)
  • North Side Municipal Beach (0.6 mi / 1 km)
  • Old Plank Road Trail Head (2.4 mi / 3.8 km)
  • Kohler Park Dunes State Natural Area (5.8 mi / 9.4 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 property in Sheboygan. Spend your time here to savor the relaxation and convenience that comes with having the whole place to yourself.
What is the most popular type of vacation rental accommodation in Sheboygan?
Condos are the most popular kind of vacation rental in Sheboygan, according to our data. Even if you’ve got a different idea in mind, Vrbo has properties in loads of shapes and sizes. Look through our options to find your perfect pad.
How much does it cost to rent a vacation rental in Sheboygan?
Length of stay, property type and time of year are some of the things that can determine the price of a vacation home. Simply click on your travel dates to find your dream escape. From comfy cabins to sprawling luxury villas, all Vrbo vacation rentals provide unbeatable value.
How much does it cost to rent a beach house in Sheboygan?
When you travel and the size and style of the property will influence the cost of your beachside escape. Put in your Sheboygan travel dates to see all your options on Vrbo. Did someone just say “hot tub”? Use our filters to pick the features and amenities you want in your beach house.
Are there pet-friendly vacation rentals in Sheboygan?
Good news! Yes. You’ll have your pick of 18 vacation rentals that allow pets in Sheboygan. Plenty of our pet-friendly vacation rentals even come with an outdoor area for your four-legged pal to run around in, complimentary treats, doggie beds and proximity to parks or green space. Apply the “Pets allowed” filter to find your pawfect digs on Vrbo.
Can I rent a house with a pool in Sheboygan?
Grab your swimwear and pool noodle, because there are two houses with a private pool in Sheboygan. Unwind at one of these sought-after vacation homes and every day can be a pool day. Simply enter your dates into Vrbo, then use the “pool” filter to find the perfect place to make a splash!
Are there vacation rentals in Sheboygan that welcome kids?
Sheboygan has 18 family-friendly vacation homes. And tracking down a stay that welcomes children is easy with our “Properties good for families” filter. In addition to having the entire place to yourselves, you’ll also get access to conveniences and perks such as bunk beds, kitchens and pools.
What are the top attractions for families in Sheboygan?
There are lots of amazing things to see and do with the family in Sheboygan, such as:

  • Sheboygan County Historical Museum
  • Blue Harbor Resort & Conference Center Water Park
  • Whistling Straits Golf Course

Are there vacation rentals with WiFi in Sheboygan?
Whether you’d like to stay in touch with the news, make a video call or surf your social networks, there are 12 vacation homes with WiFi in Sheboygan. Check the “WiFi” box when searching on Vrbo and stay connected on your vacation.
How can I find vacation rentals with air conditioning in Sheboygan?
Work out your travel dates and then use our filter tool to see vacation rentals with air conditioning in Sheboygan on Vrbo. With 16 air-conditioned properties to choose from here, you can enjoy a cool and comfortable stay.
How old do you have to be to rent a vacation rental in Sheboygan?
The age limit can vary across properties on Vrbo, so double-check the rules of the vacation home in Sheboygan you want. But usually, it’s 16, 18 or 21.
How long can I rent a vacation rental in Sheboygan for?
It’s up to the Sheboygan property. To look at a list of options offering extended stays, simply type your dates and number of guests into Vrbo. Look forward to having the entire place to yourself, as well as amenities such as air conditioning, a kitchen and outdoor spaces where the kids can run around and play. Keep your eyes peeled for long-term stays that offer weekly or monthly discounts.
Does Vrbo offer discounts for vacation homes in Sheboygan?
Overnight trip or a much-needed extended escape, Vrbo has some bargain deals and special discounts in Sheboygan that’ll suit your style and budget. Browse our weekly and monthly discounts on vacation rentals, or see what’s recently been added with one of our newly listed homes. Whatever kind of getaway you’re after, you’ll find the ideal place to stay — without spending a fortune.

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