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Sheboygan holiday lettings

We found 410 holiday rentals — enter your dates for availability

Select from 95 houses, 33 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:5 Dec - 12 Dec
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Find out more about Sheboygan

Find out more about Sheboygan

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)
  • North Side Municipal Beach (0.6 mi / 1 km)
  • Old Plank Road Trail Head (2.4 mi / 3.8 km)
  • Sheboygan Indian Mound Park (3.7 mi / 6 km)
  • Kohler Park Dunes State Natural Area (5.8 mi / 9.4 km)
  • Dairyland Park (11.8 mi / 19 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?
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 rental accommodation in Sheboygan?
Condos are the most popular style of holiday rental in Sheboygan, according to our data. Even if you have something else in mind, Vrbo 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 rental in Sheboygan?
A range of things influence what you'll pay for your holiday rental 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 Vrbo. 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 rentals 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 rentals and find a stay that's pawfect on Vrbo.
What are popular rental amenities in Sheboygan?
A water view, a lake view and tennis are the most popular rental amenities in Sheboygan. Whether you're taking a trip by yourself, with your significant other or as a family group, Vrbo will help you find a holiday home that matches your style with all the conveniences you're looking for.
Are there large group holiday rentals in Sheboygan?
Sheboygan has two holiday rentals 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 rentals 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 rentals in Sheboygan?
Gather your loved ones and enjoy a relaxing escape in one of the 15 two-bedroom holiday rentals Sheboygan has to offer.
Are there holiday rentals with WiFi in Sheboygan?
Pick from 20 holiday rentals 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 Vrbo.
How can I find holiday rentals with air conditioning in Sheboygan?
There are 42 Vrbo 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 rental in Sheboygan?
The minimum required age is generally 16, 18 or 21. It can change between properties on Vrbo, so look at the rules of your preferred Sheboygan holiday home before you book.
How long can I rent a holiday rental in Sheboygan for?
The amount of time you can stay in a Sheboygan holiday rental 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 Vrbo holiday rentals may also offer weekly or monthly discounted prices, so you can stay longer for less money.

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