Discover Your Perfect Sheboygan Vacation Homes

Best Vacation Homes in Sheboygan

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Sheboygan Luxury Rentals

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Find More Sheboygan Villas, Resorts, & Rentals on BedroomVillas

Sheboygan Pet Friendly Vacation Rentals

9.0 (1015 Reviews)
Hotel
Harbor Town Inn
  • Air Conditioner
  • Parking
  • Pet Friendly
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10.0 (12 Reviews)
Apartment
2nd floor loft near the lake!
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
View Availability
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Sheboygan Large Vacation Homes

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Why Choose Rent By Owner for your Sheboygan Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Sheboygan Vacation Rentals

Where are the best neighborhoods to stay in Sheboygan?

When exploring Sheboygan, Wisconsin, choosing the right neighborhood to stay in can greatly enhance your visit. Whether you prefer to be close to the vibrant city center or enjoy a peaceful retreat near serene waterfront views, each area offers unique appeal. By selecting a well-suited location within Sheboygan, you ensure easy access to local attractions and a comfortable base for your adventures. Trustworthy vacation rentals in this charming city provide the perfect foundation for a memorable trip, combining convenience with a genuine sense of community.

Downtown

Staying in the downtown area places you at the heart of Sheboygan's vibrant city life, offering convenient access to local shops and cultural venues. Here, you'll find a variety of comfortable vacation rentals that put you close to the region's most appealing attractions.

View 188+ Rentals in Downtown

Ellis Historical District

Nestled in the charming Ellis Historical District, this neighborhood provides a unique opportunity to enjoy Sheboygan’s rich heritage through beautifully preserved architecture. It’s an ideal choice for travelers seeking authentic vacation rentals immersed in the area's storied past.

View 201+ Rentals in Ellis Historical District

Raider

The Raider neighborhood offers a serene setting with easy access to local parks and recreational spaces, making it perfect for outdoor enthusiasts. Vacation rentals here allow you to experience a peaceful side of the region while staying close to nature and community amenities.

View 200+ Rentals in Raider

Best Times to Visit Sheboygan

When should you plan your Vacation Rentals stay?

Choosing the right time to visit ensures you experience the best of your stay here, whether you're seeking warm summer days or a peaceful off-season retreat in this scenic region.

Peak Season Highlights

summer
Summer (June to August)

This is the most popular time to visit for warm weather and outdoor activities, making it an ideal period for enjoying the scenic beauty of this destination.

Average Temperature Daytime: around 75-85°F - Nighttime: around 60-65°F
autumn
Fall (September to November)

During this season, the area transforms with vibrant fall foliage, attracting visitors seeking picturesque views and outdoor adventures.

Average Temperature Daytime: around 65-75°F - Nighttime: around 45-55°F

Off-Season Highlights

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Winter (December to February)

With colder temperatures and fewer visitors, this period offers a quiet escape for those looking to enjoy winter serenity in the region.

Average Temperature Daytime: around 25-35°F - Nighttime: around 15-25°F
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Spring (March to May)

As the region transitions into warmer weather, you can experience fewer crowds and the early signs of blooming nature here.

Average Temperature Daytime: around 45-60°F - Nighttime: around 30-40°F

Weekly Weather Forecast for Sheboygan

How to Book Your Sheboygan Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Sheboygan

More Top-Rated Vacation Rentals in Sheboygan Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy a private outdoor grilling area to prepare meals with friends or family while taking in the fresh air.
  • Take advantage of spacious patios or decks perfect for relaxing or entertaining outdoors.
  • Make use of well-maintained lawns and gardens that provide a peaceful setting for outdoor activities.
  • Benefit from outdoor dining spaces that allow you to savor meals while enjoying the region’s pleasant weather.
  • Seek out a fire pit or outdoor fireplace to gather around during cooler evenings in this scenic destination.
  • Utilize available parking areas designed for easy access to outdoor adventures in the area.
  • Explore nearby outdoor recreational facilities such as walking trails or parks that complement your stay at these vacation rentals.

Top Attractions Around Sheboygan

What attractions are nearby?

Here, you can enjoy a variety of outdoor activities such as boating, fishing, and scenic walks along the waterfront, all just moments from your Sheboygan vacation rental in Wisconsin.

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Family Activities

  • Sheboygan County Fairgrounds: Discover family-friendly events and exhibitions that make for a fun day out in the area.
  • Blue Harbor Resort & Conference Center Water Park: Enjoy a day of splashing and relaxing at this popular water park, perfect for kids and parents alike.
  • Bookworm Gardens: Explore this whimsical garden inspired by children’s literature, offering engaging outdoor activities for all ages.
  • North Point Lighthouse: Take a guided tour of this historic lighthouse and enjoy stunning views of Lake Michigan suitable for family adventures.
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Adult Activities

  • Visit the John Michael Kohler Arts Center: Immerse yourself in innovative art exhibitions and cultural experiences that highlight this destination's vibrant creative scene.
  • Explore the Kohler Design Center: Discover inspiring interior design displays and learn about the region’s renowned craftsmanship, perfect for design enthusiasts staying in local vacation rentals.
  • Relax at North Point Park: Enjoy scenic views of Lake Michigan while strolling along walking trails or relaxing on the beach near your Sheboygan accommodations.
  • Experience local craft breweries: Sample regional brews at popular breweries in the area, offering a taste of Sheboygan’s vibrant craft beer culture for visitors lodging nearby.

Other Places to Stay in Sheboygan, WI

Sheboygan County
Sheboygan County Vacation Rentals
Ellis Historical District
Ellis Historical District Vacation Rentals
Downtown
Downtown Vacation Rentals
Sheboygan Falls
Sheboygan Falls Vacation Rentals
Rhine
Rhine Vacation Rentals
Elkhart Lake
Elkhart Lake Vacation Rentals
Plymouth
Plymouth Vacation Rentals
Two Rivers
Two Rivers Vacation Rentals
Manitowoc
Manitowoc Vacation Rentals
Calumet County
Calumet County Vacation Rentals
Chilton
Chilton Vacation Rentals
Campbellsport
Campbellsport Vacation Rentals
More Places to Stay Near Sheboygan

Sheboygan Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Cuisine: Take advantage of the region's fresh seafood and local eateries to enjoy authentic flavors unique to this destination.
  • Visit Waterfront Areas: Spend time along the lakeshore to experience the natural beauty and relaxing atmosphere that make this area special.
  • Plan Outdoor Activities: Engage in biking, hiking, or water sports to maximize your outdoor adventure in the setting that defines this region.
  • Discover Cultural Attractions: Immerse yourself in the local arts, history, and community events that highlight the area's rich heritage.

Transportation Options

  • Sheboygan County Memorial Airport: This regional airport offers convenient flights and transportation options for travelers arriving in the area.
  • Amtrak Rail Service: The train station provides an accessible way to explore this destination and neighboring cities along the route.
  • Local Bus Services: Public transportation throughout the region allows easy travel between popular points of interest in Sheboygan.
  • Car Rentals and Taxis: Renting a vehicle or hiring a taxi can give you flexible access to scenic spots and local amenities here.

Local Customs Options

  • Sheboygan County Fair Tradition: You will find that local fairs here celebrate community spirit with traditional rides, exhibits, and food that showcase the area's rich agricultural roots.
  • Lake Michigan Seafood Celebrations: Enjoy the region’s culinary customs by indulging in fresh fish and seafood, especially during seasonal festivals and local gatherings.
  • Boating and Maritime Customs: Sheboygan's proximity to Lake Michigan fosters a culture of boating and maritime activities, which are central to the area's outdoor lifestyle.
  • German Heritage Festivals: The region embraces its German roots through lively festivals featuring authentic music, dance, and cuisine that reflect its cultural heritage.

Frequently Asked Questions About Sheboygan?

1. What are the top vacation rentals in Sheboygan?

There are a lot of options in Sheboygan. If you plan on staying in the Sheboygan area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Sheboygan:

2. How many vacation rentals have private pools in Sheboygan?

There are 28 vacation rentals with private pools near Sheboygan. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Sheboygan are best for families?

If you are looking for a family-friendly vacation home in Sheboygan, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Sheboygan:

4. How many Rentbyowner vacation rentals are available in Sheboygan?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 761 in the Sheboygan area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Sheboygan. 

5. What is the cancellation policy for vacation rentals in Sheboygan, Wisconsin?

Cancellation policies vary by listing. You should review the specific cancellation terms listed on the property page or contact the owner directly to understand the options available for your booking.

6. How do I confirm availability and make a reservation in Sheboygan area?

Availability is updated regularly by the property owners. To book, simply select your preferred dates on the listing and follow the booking process, or reach out to the owner for further assistance.

7. Are there any house rules or restrictions I should be aware of when staying in this region?

Yes, each property has its own house rules and restrictions, which are detailed in the listing. It’s advisable to read these carefully before completing your reservation or contacting the owner with any questions.

8. Is parking included with my vacation rental in Sheboygan, Wisconsin?

Parking arrangements differ between properties. Please check the specific listing details or contact the owner to confirm if parking is included and what options are available during your stay.

9. What amenities are typically available in Sheboygan vacation rentals?

Most properties offer essential amenities such as Wi-Fi, kitchen facilities, and linens. For a detailed list of amenities, refer to the individual listing or contact the owner directly to ensure it meets your needs.

Sheboygan Top Rated Vacation Rentals

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