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Sheboygan holiday lettings

We found 407 holiday rentals — enter your dates for availability

Select from 96 houses, 27 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:24 Apr - 1 May

Image gallery for Entire mansion with indoor pool! Perfect for hosting groups. On Lake Michigan

Terrace/patio
10 out of 10, Exceptional, (45 reviews)
Exceptional
(45 reviews)

Entire mansion with indoor pool! Perfect for hosting groups. On Lake Michigan

Newton

11% off
Price is £13,289
for 7 nights, 1 home
£1,898 per night
includes taxes & fees
Entire mansion with indoor pool! Perfect for hosting groups. On Lake Michigan

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Why visit Sheboygan

  • Scenic Waterfront: Enjoy the picturesque views of Lake Michigan, perfect for romantic strolls and relaxing afternoons.
  • Outdoor Adventures: Engage in various outdoor activities, from hiking to water sports, catering to adventure enthusiasts.
  • Cultural Experiences: Discover local art and history at vibrant museums and botanical gardens throughout the city.
  • Charming Downtown: Explore inviting shops and cafes in the lively downtown area, ideal for leisurely exploration.
  • Diverse Accommodation: Choose from a range of delightful places to stay, including cosy cottages and modern condos.

Popular types of accommodation in Sheboygan

If you're contemplating a getaway to Sheboygan, worry not about your accommodation options. Our platform offers a range of delightful choices, including houses, charming cottages, and modern condos. Whether you're searching for Sheboygan holiday rentals or a cosy apartment in Sheboygan, we have the ideal place for you. Enjoy transparency, savings, and peace of mind as you explore the best apartment rentals in Sheboygan, WI!

  • Houses: The top choice for visitors in Sheboygan, ideal for families, couples, or groups seeking comfort and privacy.
  • Cottages: A charming option for those desiring a quaint, picturesque stay, perfect for a romantic getaway or a peaceful retreat.
  • Condos: A popular alternative offering modern amenities and convenient locations for a hassle-free experience.
  • Apartments: A versatile choice that caters to various needs, providing a homely atmosphere in the heart of the city.
  • Cabins: A delightful option for nature lovers, offering a rustic experience surrounded by serene landscapes.**

Top attractions in and around Sheboygan

Sheboygan offers a delightful blend of outdoor activities and scenic beauty, making it ideal for romantic getaways. Visitors can explore a variety of attractions, including art museums, local museums, and botanical gardens. This charming destination caters to those seeking cultural experiences, family-friendly activities, and opportunities to immerse themselves in nature. Whether you’re travelling solo, as a couple, or with family, Sheboygan has something to enchant every tourist.

  • John Michael Kohler Arts Center: This vibrant art museum showcases contemporary and folk art, featuring immersive exhibitions that reflect the cultural diversity of the region, providing a unique insight into local creativity.
  • Kohler Design Center: Located 1.9km from Sheboygan, this museum highlights innovative design and craftsmanship, particularly in kitchen and bath fixtures, blending art and practicality to inspire home aesthetics.
  • Above & Beyond Children's Museum: Situated in Sheboygan, this interactive museum offers engaging exhibits for families, fostering creativity and learning through play, making it a delightful experience for children and adults alike.

Things to do recommended for couples

For a romantic getaway in Sheboygan, consider dining at Antoinette, a charming restaurant located 8.1km away. With its lovely ambiance perfect for couples, you can enjoy a delightful meal while soaking up the intimate atmosphere, making it a memorable experience for both of you.

Things to do recommended for families

Families visiting Sheboygan can have a splashing good time at the Blue Harbor Resort & Conference Center Water Park, offering thrilling water fun. For a serene escape, Kohler-Andrae State Park, located 4.3km away, provides a lovely setting for relaxation and outdoor adventure.

Things to do recommended for groups

Experience the stunning Whistling Straits Golf Course for a memorable day of outdoor sports. Enjoy a captivating performance at the Stefanie H. Weill Center for the Performing Arts, perfect for family and romance. Don't forget to visit Evans, a delightful store just 3.1km from Sheboygan.

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

If you're travelling with a group, family, or pets, or if you're considering longer stays, it's important to filter your options according to your key priorities. Here are some helpful tips for booking on Vrbo.

  • Traveling to Sheboygan with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily apply filters for all of these options, and many more, on Vrbo.
  • Traveling to Sheboygan with young kids: Travelling with young children can present some challenges. It's important to prioritise their comfort and safety, along with 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 trip isn’t truly fulfilling without their furry companion by their side. If you can relate, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortably at home.
  • Planning for a long term stay visiting Sheboygan: If you’re searching for holiday rentals with discounts for stays of a month or more, you’ve come to the right place. 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 criteria as well.

Where to stay near Sheboygan

Sheboygan, a charming city on the shores of Lake Michigan, offers a delightful blend of outdoor adventures and romantic settings. Explore the vibrant downtown, where lively streets are lined with inviting shops and cafes. Don't miss the serene Sheridan Park for a relaxing stroll or a family-friendly outing. Whether you're basking by the fireplace or enjoying the scenic waterfront, Sheboygan promises a memorable vacation experience filled with enchanting vibes.

  • Kohler: Kohler is a picturesque city located 2.5km from Sheboygan, renowned for its stunning outdoor scenery and a plethora of sporting activities. This charming destination is particularly famous for its exceptional golf courses, set against a backdrop of lush landscapes. Visitors can enjoy a range of recreational areas, perfect for leisurely strolls or picnics. Nearby, you'll find beautiful lakes and beaches, along with the serene Kohler-Andrae State Park, which offers hiking trails and panoramic views, making it an ideal spot for nature enthusiasts.
  • Sheboygan Falls: Situated 3.1km from Sheboygan, Sheboygan Falls is a delightful city perfect for families and outdoor lovers alike. This area boasts a variety of attractions, including a thrilling water park and expansive recreational areas. Golf enthusiasts can also find excellent courses nearby. The local landmarks, such as the serene lakes and a vibrant racetrack, provide a mix of relaxation and excitement. The event conference venue is great for those looking to engage in local happenings or events, ensuring there's something for everyone.
  • Oostburg: Oostburg, located 6.2km from Sheboygan, is a charming city offering a romantic atmosphere and breathtaking outdoor scenery. Ideal for couples and nature lovers, it features lovely recreational areas and a water park for a bit of fun. The proximity to beautiful lakes, inviting beaches, and the scenic national state park enhances its appeal. Visitors can enjoy leisurely walks, picnic spots, and a variety of outdoor activities, making Oostburg an enjoyable retreat for those seeking both adventure and tranquillity.

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 aiming to save on your upcoming getaway? Being flexible with your travel dates can be beneficial, as prices often fluctuate. Additionally, booking a longer stay can lead to considerable savings. To discover a Vrbo property that suits your budget, simply use our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board offers a handy platform for planning your journeys. You can easily create new trips, resume from where you last stopped, or manage your existing plans. The properties you’ve saved or booked are neatly organised into categories: Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.vrbo.com/en-gb/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)
  • Evans (5.2 mi / 8.3 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:

  • Bookworm Gardens (2.2 mi / 3.5 km)
  • Kohler Park Dunes State Natural Area (5.8 mi / 9.4 km)
  • North Beach (17.8 mi / 28.7 km)
  • South Beach (18.7 mi / 30.1 km)
  • Sheboygan Marsh State Wildlife Area (20.2 mi / 32.5 km)
  • North Side Municipal Beach (0.6 mi / 1 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 rental?
When considering a holiday rental in Sheboygan, Wisconsin, the best area to stay is the Riverfront District. This vibrant neighbourhood is known for its charming atmosphere and proximity to the Sheboygan River, making it an excellent choice for those looking to enjoy scenic views and outdoor activities. With a variety of properties available, from quaint cottages to modern apartments, visitors will find numerous options to suit their needs.

In addition to the picturesque riverwalk, the Riverfront District is conveniently located near the John Michael Kohler Arts Centre, which showcases captivating art exhibitions and performances. The area is also close to Sheboygan's beautiful beaches, where you can relax or partake in water sports. Exploring this lively neighbourhood offers a delightful mix of culture and leisure, ensuring a memorable stay in Sheboygan.

Another great option is the North Point area, which is known for its stunning lakeside views and proximity to the iconic Kohler-Andrae State Park. This area is ideal for nature lovers, offering an abundance of outdoor activities like hiking, birdwatching, and beachcombing. Properties here tend to be spacious and family-friendly, making it a wonderful choice for those looking to immerse themselves in the natural beauty of the region.
How much does it cost to rent a holiday home in Sheboygan?
Prices for holiday 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 holiday 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, Wisconsin, the area along the shores of Lake Michigan is ideal. The North Beach neighbourhood is particularly popular, known for its sandy stretches and family-friendly atmosphere. Here, travellers can find beach houses with amenities such as large decks, outdoor grills, and direct access to the beach, great for enjoying summer days by the water. Many properties in this area are equipped with modern kitchens and spacious living areas, allowing guests to comfortably host gatherings after a day of sun and surf.

Additionally, the South Pier area offers a vibrant atmosphere, where beach houses often provide stunning views of the lake and easy access to local attractions like the Sheboygan Breakwater Lighthouse. Rentals in this neighbourhood might feature amenities such as balconies, fire pits, and proximity to local dining options and shops. Find your rental near the beach in Sheboygan.
What is the most popular type of holiday rental accomodation in Sheboygan?
In Sheboygan, holiday houses are the most popular type of accommodation, with around 66 available across the area. These properties provide ample space, often featuring multiple bedrooms and spacious living areas, making them ideal for families or groups. Many of these houses come with fully equipped kitchens, outdoor patios or decks, and sometimes even private gardens, allowing guests to enjoy the beautiful surroundings.
Are there any family house rentals in Sheboygan?
In Sheboygan, Wisconsin, there are numerous family-friendly house rentals available—specifically, around 88 options throughout the area. Visitors will find accommodations in various neighbourhoods, including those near the picturesque shoreline of Lake Michigan. Many of these homes provide spacious living arrangements, allowing families to enjoy quality time together.

Common amenities include fully equipped kitchens superb for preparing family meals, comfortable living rooms for relaxation, and outdoor spaces where children can play. Some properties may even feature additional perks like game rooms or fire pits for evening gatherings under the stars.
Can I rent a holiday home with a pool or hot tub in Sheboygan?
In Sheboygan, there are several holiday homes available for rent that feature pools and hot tubs. This charming city, located along the shores of Lake Michigan, offers a variety of neighbourhoods where these properties can be found, including the scenic areas near Deland Park and the lakeside communities that provide easy access to the beach.
Can I find long-stay holiday rentals in Sheboygan?
A long-stay holiday rental in Sheboygan is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Sheboygan?
In Sheboygan, there are numerous pet-friendly house rentals available, with around 42 options for travellers to choose from. These rentals often come equipped with amenities such as spacious living areas, fully stocked kitchens, and outdoor spaces, making them ideal for families or groups travelling with pets. Many properties feature private yards or patios, allowing for easy outdoor access for your furry friends.
Are there any remote work holiday rentals in Sheboygan?
In Sheboygan, Wisconsin, there are numerous remote work holiday rentals available, with around 122 options to choose from. This charming lakeside city offers a variety of properties that cater to remote workers, ensuring a comfortable and productive stay. Many rentals come equipped with essential amenities such as high-speed Wi-Fi, dedicated workspace areas, and ergonomic furniture including desks and chairs, providing an ideal environment for working from home. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Sheboygan holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Sheboygan with parking available—perfect for families or travellers 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 rental amenities include well-equipped kitchens featuring stovetops, microwaves, and refrigerators, allowing travellers to prepare their meals comfortably. Most holiday rentals also come with cookware, dishware, and utensils, making it easy for guests to dine in after a day of exploring the area's attractions, such as the picturesque shoreline along Lake Michigan and the nearby Kohler-Andrae State Park.
When is the best time to visit Sheboygan for a holiday rental?
The best time to visit Sheboygan for a holiday rental is during the vibrant peak season from May to July. This period attracts outdoor enthusiasts and beachgoers, as the weather warms up and the beautiful shores of Lake Michigan come alive with activity. Visitors can enjoy a variety of water sports, from sailing to kayaking, and take in the stunning sunsets that the area is famous for.

May, in particular, is a fantastic month to experience Sheboygan. With temperatures typically in the mid-teens Celsius, it's ideal for exploring the picturesque beaches and scenic parks without the summer crowds. The blooming flowers and lush greenery create a great backdrop for leisurely strolls along the lakeshore or bike rides on the nearby trails.

For those seeking a more budget-friendly option, November can be a lovely time to visit. While the summer buzz has faded, it offers a unique charm with fewer tourists and opportunities to enjoy the local culture at a more relaxed pace. You can discover cosy cafes and explore the local art scene, all while savouring the crisp autumn air.
How early should I book a Sheboygan holiday rental?
Book your Sheboygan holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Sheboygan?
In Sheboygan, visitors can enjoy a variety of attractions that highlight the city's charm and natural beauty. The picturesque waterfront along Lake Michigan is superb for leisurely strolls, and the nearby Sheboygan Breakwater Lighthouse is a popular landmark offering scenic views. The historic downtown area features unique shops, cafes, and local eateries, providing a delightful atmosphere for those looking to explore.
Can I change or cancel my Sheboygan home rental booking on Vrbo?
To find Sheboygan holiday 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 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 travellers 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 cosy cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, 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 organising 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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