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Sheboygan vacation rentals

We found 400 vacation rentals — enter your dates for availability

Select from 96 houses, 32 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.

Vacation rentals with weekly discounts - Sheboygan

Showing deals for:Jun 5 - Jun 12

Image gallery for Road America Adjacent Lake House with indoor pool

Pool
9.8 out of 10, Exceptional, (36 reviews)
Exceptional
(36 reviews)

Road America Adjacent Lake House with indoor pool

Plymouth

8% off
Price is $760
$5,322 for 7 nights
All fees included
Road America Adjacent Lake House with indoor pool

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Find out more about Sheboygan

Why visit Sheboygan

  • Outdoor Adventures: Enjoy a variety of activities such as hiking, biking, and water sports in the beautiful natural surroundings.
  • Cultural Experiences: Visit art museums and landmarks that showcase local history and creativity.
  • Charming Downtown: Explore unique shops and eateries in the vibrant downtown area of Sheboygan.
  • Scenic Getaways: Discover picturesque landscapes ideal for romantic retreats and family-friendly outings.
  • Diverse Accommodations: Choose from cozy cottages, stylish condos, and private vacation homes to suit your preferences.

Popular types of accommodation in Sheboygan

If you're looking for the perfect getaway in Sheboygan, you're in luck. Our platform offers a range of popular vacation rental options, including houses, cozy cottages, and stylish condos. Whether you seek affordable rentals or specific amenities, you'll find a variety of Sheboygan apartments that suit your needs. Start planning your ideal stay today and enjoy all that Sheboygan has to offer.

  • Houses: The top choice for visitors in Sheboygan, offering spacious accommodations ideal for families or groups looking for a home-like experience.
  • Cottages: A charming option, these cozy retreats provide a quaint atmosphere for a relaxing stay by the lake or in nature.
  • Condos: Perfect for those seeking modern amenities, condos offer convenience and comfort in a community setting.
  • Apartments: A practical choice for solo travelers or couples, apartments provide a home base with essential facilities.
  • Cabins: Rustic and inviting, cabins are a great way to enjoy Sheboygan’s scenic beauty while embracing a cozy vibe.**

Top attractions in and around Sheboygan

Sheboygan, Wisconsin, is a fantastic destination for outdoor enthusiasts and those seeking scenic, romantic getaways. Visitors can explore a variety of attractions, including art museums, landmarks, and botanical gardens. Whether you're traveling with family or looking for a cultural experience, Sheboygan offers a range of points of interest that cater to diverse interests and activities, making it an ideal spot for your next vacation.

  • John Michael Kohler Arts Center: This vibrant art museum features diverse exhibitions that celebrate creativity and culture, making it a hub for art enthusiasts. The center often showcases local and international artists, providing a unique insight into contemporary art.
  • Bookworm Gardens: A whimsical botanical garden that delights families with its imaginative landscapes and storybook themes. It's a perfect spot for leisurely strolls, romantic picnics, and children’s exploration, offering a magical outdoor experience.
  • North Side Municipal Beach: A beautiful stretch of sandy shoreline located 0.6 miles from Sheboygan, ideal for relaxing, swimming, and beach activities. Enjoy the refreshing lake breeze and stunning sunsets on this picturesque beach.

Things to do recommended for couples

If you're seeking a romantic getaway in Sheboygan, consider dining at Antoinette, just 13 miles away. This charming restaurant offers a delightful ambiance perfect for couples, blending city vibrance with a cozy, intimate feel. Enjoy a memorable meal together and create lasting memories.

Things to do recommended for families

Your family will have a blast at the Blue Harbor Resort & Conference Center Water Park, where adventure awaits. Don't miss the natural beauty of Kohler-Andrae State Park, just 7 miles from Sheboygan, perfect for relaxation and outdoor fun.

Things to do recommended for groups

Experience the stunning Whistling Straits Golf Course for a day of outdoor fun, then enjoy a captivating performance at the Stefanie H. Weill Center for the Performing Arts. Don't forget to visit Evans, a unique store just 5 miles from Sheboygan for some local shopping.

*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

If you're traveling with a group, with family, bringing pets, or planning an extended stay, be sure to use the appropriate filters to meet your needs. Here are some helpful booking tips for Vrbo.

  • Traveling to Sheboygan with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor space for group gatherings. Luckily, you can easily filter for all these options and more on Vrbo.
  • Traveling to Sheboygan with young kids: Traveling with young kids can be a bit tricky. It's important to prioritize their comfort and safety, along with finding suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Sheboygan: For many families, a vacation wouldn't be the same without their furry companion. If you can relate, explore Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and 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 that offer discounts 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 rental options. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in and around Sheboygan

Sheboygan, Wisconsin, offers a delightful blend of outdoor adventures and charming scenery, making it perfect for romantic getaways and family-friendly vacations. Explore the vibrant downtown Sheboygan, with its unique shops and eateries, or venture to nearby cities that boast picturesque landscapes and relaxing atmospheres. Whether you're looking for cozy vacation homes or memorable experiences, Sheboygan and its surrounding neighborhoods promise an unforgettable travel experience.

  • Kohler: Located a mere 4 miles from Sheboygan, Kohler is a charming city known for its stunning outdoor scenery and recreational opportunities. Travelers flock to Kohler for its renowned golf courses and beautiful parks, where you can enjoy a day of sports or simply take in the lush landscapes. Key attractions nearby include picturesque lakes and scenic beaches, perfect for a relaxing afternoon. Additionally, the nearby Kohler-Andrae State Park offers trails and stunning views of Lake Michigan, making it an ideal spot for nature lovers and outdoor enthusiasts alike.
  • Sheboygan Falls: Just 5 miles from Sheboygan, Sheboygan Falls is a delightful city that offers a family-friendly atmosphere and outdoor adventures. Visitors can enjoy a variety of activities, including water parks and recreational areas, making it a great destination for families. The city is also home to a beautiful lake and a local racetrack that hosts exciting events throughout the year. With its charming parks and community events, Sheboygan Falls provides a welcoming experience for those looking to explore the beauty of Wisconsin.
  • Downtown Sheboygan: The vibrant Downtown Sheboygan neighborhood is located in the heart of the city and offers an array of entertainment options for families and visitors. Here, you can explore exciting attractions like water parks and recreational areas, as well as enjoy the local dining scene. The area also features a conference venue that hosts various events, ensuring there's always something happening. With its lively atmosphere and proximity to Lake Michigan, Downtown Sheboygan is a perfect base for exploring the region’s outdoor activities and entertainment offerings.

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 January to March tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January22.6°F (-5.2°C)No Rain (Dry)Mostly CloudyLowAverage
February22.8°F (-5.1°C)No Rain (Dry)Mostly CloudyLowSlightly Low
March32.7°F (0.4°C)Light RainMostly CloudyLowSlightly Low
April40.8°F (4.9°C)Light RainMostly CloudyAverageSlightly Low
May51.4°F (10.8°C)Light RainMostly SunnyAverageAverage
June62.2°F (16.8°C)Light RainMostly SunnyHighAverage
July70.0°F (21.1°C)Light RainMostly SunnyHighSlightly High
August70.0°F (21.1°C)Light RainMostly SunnyHighSlightly High
September63.9°F (17.7°C)Light RainMostly SunnyAverageSlightly High
October52.0°F (11.1°C)Light RainMostly SunnyAverageAverage
November39.9°F (4.4°C)Light RainMostly SunnyAverageAverage
December30.0°F (-1.1°C)Light RainMostly CloudyAverageAverage

Booking with Vrbo is a breeze

Are you hoping to save on your next getaway? Being flexible with your travel dates can really make a difference, as prices tend to vary. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, be sure to utilize our filters to sort by price, location, and type of vacation rental.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your booking. Being the planner has its perks. By enrolling in our travel rewards program, One Key, you can quickly access exclusive member savings and earn OneKeyCash on eligible reservations. Join us today and start enjoying the benefits.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board is designed to help you plan your travel effortlessly. Here, you can create new trips, pick up where you left off, and manage your bookings all in one place. Your saved or booked properties are conveniently categorized into Potential, Upcoming, or Current Trips for easy access. To discover more about Trip Boards, please visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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)
  • 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:

  • North Side Municipal Beach (0.6 mi / 1 km)
  • Bookworm Gardens (2.2 mi / 3.5 km)
  • Kohler Park Dunes State Natural Area (5.8 mi / 9.4 km)
  • South Beach (18.7 mi / 30.1 km)
  • Sheboygan Indian Mound Park (3.7 mi / 6 km)
  • Dairyland Park (11.8 mi / 19 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, Wisconsin, United States of America when booking a vacation rental?
When considering a vacation rental in Sheboygan, a fantastic area to stay is near the lakefront, particularly in neighborhoods that offer easy access to both the water and local attractions. This area features a variety of properties, ranging from cozy cottages to modern condos, providing options for different group sizes and preferences.

Staying near the lakefront allows you to enjoy stunning views and the refreshing ambiance of Lake Michigan. It's also conveniently located close to popular attractions such as the John Michael Kohler Arts Center, which showcases a diverse array of art and cultural events, and the beautiful Sheboygan Breakwater Lighthouse, superb for scenic walks. Furthermore, this region is known for its vibrant dining scene, where you can indulge in local cuisine.

Another great option is neighborhoods that are a bit more inland, where you can find charming residential streets and easy access to parks and recreational areas. These neighborhoods often feature a more laid-back atmosphere while still being a short drive from the lake and downtown attractions. You'll find a mix of properties here, suiting families seeking a homey feel while being close to the heart of Sheboygan's activities.
How much does it cost to rent a vacation home in Sheboygan?
Prices for vacation rentals in Sheboygan vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Sheboygan to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Sheboygan vacation house rentals?
You can find great discounts on house rentals in Sheboygan on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Sheboygan?
For renting a beach house in Sheboygan, the area along Lake Michigan's shoreline is a prime choice. The North Beach neighborhood is particularly appealing, known for its beautiful sandy beaches and family-friendly atmosphere. Here, travelers can find vacation rentals that often include amenities such as private decks, outdoor grills, and easy access to the beach, making them great for summer gatherings and relaxation by the water.

Additionally, the area surrounding Sheboygan's popular deland Park is worth considering, as it offers proximity to both the beach and local attractions. Properties in this vicinity may feature spacious living areas, fully equipped kitchens, and sometimes even access to community amenities like pools or tennis courts. The park itself provides lovely walking paths and picnic areas, enhancing the outdoor experience.

For those interested in a more vibrant setting, the downtown Sheboygan area showcases a mix of historic charm and modern conveniences. Here, travelers can find properties with stunning lake views, close to local dining and shopping options. Rentals often come with amenities such as Wi-Fi, air conditioning, and laundry facilities, suiting both short and extended stays. Find your rental near the beach in Sheboygan.
What is the most popular type of vacation rental accomodation in Sheboygan?
In Sheboygan, vacation houses are the most popular type of rental, with about 62 available throughout the area. These homes often feature spacious living areas, multiple bedrooms, and fully equipped kitchens, making them ideal for families and larger groups. Many of these properties are situated near the shores of Lake Michigan, providing easy access to the beach and scenic views.

In addition to vacation houses, there are approximately 29 condos and 26 apartments, which tend to be located in more central areas, close to local shops and restaurants. These accommodations typically offer modern amenities, such as Wi-Fi and pools, suiting travelers looking for convenience and comfort. There are also around 12 charming cottages available, great for those seeking a cozy, rustic experience, often with outdoor fire pits or porches to enjoy the natural surroundings.
Are there any family house rentals in Sheboygan?
In Sheboygan, Wisconsin, there is a wide selection of family-friendly house rentals available, totaling around 90 options throughout the area. Many of these homes are situated near the beautiful shores of Lake Michigan, providing easy access to sandy beaches, parks, and outdoor activities. Families can find properties featuring spacious living rooms, fully equipped kitchens for preparing meals together, and outdoor patios or decks great for barbecues and relaxation.

Neighborhoods close to the lake, such as North Point and South Pier, offer convenient access to local attractions, including the John Michael Kohler Arts Center and Sheboygan's vibrant waterfront. Visitors can also explore nearby playgrounds and picnic areas, ensuring a fun-filled experience for children. See all family-friendly rentals in Sheboygan.
Can I rent a vacation home with a pool or hot tub in Sheboygan?
In Sheboygan, there are several vacation homes available for rent that feature pools and hot tubs. This charming city, located on the shores of Lake Michigan, offers a variety of neighborhoods where these properties can be found, including areas near the beach and parks. Travelers can expect many amenities in these rentals, such as private pools, hot tubs, outdoor seating areas, and fully equipped kitchens, making them superb for relaxation and family gatherings. Additionally, some homes may provide access to beautiful outdoor spaces, ideal for enjoying the scenic views and pleasant weather. Find your rental in Sheboygan with a pool or a hot tub.
Can I find long-stay vacation rentals in Sheboygan?
A long-stay vacation rental in Sheboygan is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Sheboygan?
In Sheboygan, travelers will find a variety of pet-friendly house rentals, with around 43 options available to choose from. Many of these vacation homes are situated close to the beautiful shores of Lake Michigan, providing easy access to the beach and scenic views. Expect amenities such as spacious backyards for pets to roam, fully equipped kitchens for preparing meals, and cozy living spaces for relaxation. Some rentals may even feature outdoor patios or decks, superb for enjoying the fresh air with your furry companions.

Additionally, Sheboygan offers nearby parks and natural areas where pets are welcome. Deland Park, located along the lake, has walking trails and green spaces, making it an excellent spot for leisurely strolls with your pet.
Are there any remote work vacation rentals in Sheboygan?
In Sheboygan, there are numerous remote work vacation rentals available, with around 117 options to choose from. This charming city along Lake Michigan offers a variety of properties suitable for those looking to blend work and leisure. Travelers can expect amenities such as free Wi-Fi, dedicated desks, and laptop workspaces, ensuring a productive environment while enjoying the scenic views of the lake. Many rentals also include comfortable living spaces and fully equipped kitchens, providing a cozy feel for extended stays.

Additionally, Sheboygan boasts beautiful parks, waterfront activities, and local attractions like the John Michael Kohler Arts Center, making it an appealing destination for remote workers who want to explore during their downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Sheboygan vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Sheboygan with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Sheboygan?
In Sheboygan, popular vacation rental amenities include fully equipped kitchens, which allow travelers to prepare their own meals conveniently. Many rentals also feature onsite parking, making it easy for guests with vehicles to access the area. Coffee and tea makers are commonly available, providing a cozy start to the day. Additionally, many properties offer decks or patios where guests can relax outside and enjoy the fresh air. Some rentals even include blenders, suiting those looking to whip up smoothies or other beverages.
When is the best time to visit Sheboygan for a vacation rental?
The best time to visit Sheboygan for a vacation rental is from May to July, when the area comes alive with vibrant summer activities. May, in particular, is a standout month, as visitors can enjoy pleasant weather with temperatures ranging from the mid-50s to the low 70s Fahrenheit. This is an ideal time for outdoor enthusiasts looking to explore the beautiful beaches along Lake Michigan or engage in water sports like kayaking and paddleboarding.

As the peak season approaches, families flock to Sheboygan for its lively community events, including festivals and concerts that create an inclusive setting. The warm summer days provide great conditions for sightseeing and enjoying the picturesque shoreline, making it a great time to soak in the natural beauty of the area.

For those looking to stretch their budgets, November is a wonderful alternative. While this month may see fewer tourists, it offers a chance to experience a quieter Sheboygan adorned in its fall colors. The crisp air is great for cozy strolls along the lakefront or exploring local shops.

Ultimately, your choice of when to visit Sheboygan will depend on your preference for lively summer activities or a more tranquil fall experience.
How early should I book a Sheboygan vacation rental?
Book your Sheboygan vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Sheboygan, Wisconsin, United States of America?
In Sheboygan, visitors can enjoy a variety of attractions that highlight the area's natural beauty and cultural offerings. The picturesque Lake Michigan shoreline is a focal point, with Sheboygan's North Beach providing a great spot for swimming, sunbathing, and picnics. Nearby, the John Michael Kohler Arts Center showcases local and international art exhibitions, making it a must-visit for art enthusiasts.

The Riverfront District is another vibrant area where visitors can explore charming shops, cafes, and restaurants. The Sheboygan County Historical Museum offers insights into the region's history, while the nearby Bookworm Gardens presents a whimsical outdoor experience that's superb for families, featuring themed gardens inspired by children's literature.

Outdoor enthusiasts can take advantage of the scenic trails at the Sheboygan Marsh and the nearby Kohler-Andrae State Park, which offers hiking, birdwatching, and stunning views of the lake.
Can I change or cancel my Sheboygan home rental booking on Vrbo?
To find Sheboygan vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Sheboygan vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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