Discover Your Perfect Sheboygan County Vacation Homes

Best Vacation Homes in Sheboygan County

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Sheboygan County Pet Friendly Vacation Rentals

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Why Choose Rent By Owner for your Sheboygan County 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.

Best Times to Visit Sheboygan County

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit here allows you to enjoy the region's unique seasonal beauty while making the most of your vacation rental experience in Sheboygan County, Wisconsin.

Peak Season Highlights

summer
Summer (June to August)

During the warm summer months, you can enjoy ideal weather for outdoor activities and exploring the scenic beauty here.

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

Early fall offers vibrant foliage and pleasant temperatures, making it a perfect time for sightseeing and outdoor adventures.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 50°F to 55°F

Off-Season Highlights

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Winter (December to February)

The winter season transforms the area into a peaceful retreat, ideal for cozy stays and winter sports enthusiasts.

Average Temperature Daytime: 20°F to 30°F - Nighttime: 10°F to 20°F
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Spring (March to May)

As nature begins to awaken, this season offers fewer crowds and a mild climate perfect for quiet exploration.

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

Weekly Weather Forecast for Sheboygan County

How to Book Your Sheboygan County 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 County

More Top-Rated Vacation Rentals in Sheboygan County 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 outdoor dining areas, perfect for savoring local flavors amidst the scenic surroundings.
  • Take advantage of private or shared patios and decks to relax and unwind in the fresh air.
  • Experience the convenience of on-site grilling facilities for a delicious barbecue with loved ones.
  • Make use of landscaped yards or gardens to stroll or simply sit back and enjoy the outdoors.
  • Benefit from access to nearby beaches or waterfronts, ideal for water activities and relaxing by the shore.
  • Utilize outdoor fire pits or fireplaces for cozy evenings under the stars.
  • Explore well-maintained outdoor spaces such as lawns or trails for walking, biking, or outdoor recreation.

Top Attractions Around Sheboygan County

What attractions are nearby?

While staying here, you can explore nearby outdoor activities, local dining experiences, and scenic spots that showcase the charm of Sheboygan County, Wisconsin, providing a perfect backdrop for your memorable getaway in this inviting region.

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Family Activities

  • Explore the Sheboygan County Historical Museum: Dive into this area's rich heritage through engaging exhibits and interactive displays that are perfect for family learning experiences.
  • Visit Bookworm Gardens: Discover this inspiring children's garden where themed gardens and whimsical landscapes captivate young imaginations in the region's family-friendly outdoor spaces.
  • Enjoy Kohler-Andrae State Park: Spend a day at this scenic coastal park, offering sandy beaches, nature trails, and picnic areas ideal for outdoor family fun along the lakeshore.
  • Attend a family event at the Boys & Girls Clubs of Sheboygan County: Participate in community activities designed to foster fun and learning for children of all ages, conveniently located here in the area.
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Adult Activities

  • Sheboygan County Brewing Tours: Explore local breweries to enjoy craft beers and learn about the region’s brewing heritage in this vibrant area.
  • Golfing at Sheboygan County Courses: Tee off at renowned golf courses that offer scenic views and challenging play, perfect for a relaxing day on the greens.
  • Wine Tasting Experiences: Visit nearby wineries to indulge in wine tasting sessions, taking in the area's burgeoning viticulture scene amidst picturesque surroundings.
  • Dining at Local Restaurants: Savor regional flavors at highly-rated restaurants that showcase the culinary diversity of this destination.

Other Places to Stay in Sheboygan County, WI

Sheboygan
Sheboygan Vacation Rentals
Downtown
Downtown Vacation Rentals
Ellis Historical District
Ellis Historical District Vacation Rentals
Sherman
Sherman Vacation Rentals
Rhine
Rhine Vacation Rentals
Elkhart Lake
Elkhart Lake Vacation Rentals
Plymouth
Plymouth Vacation Rentals
Random Lake
Random Lake Vacation Rentals
Sheboygan Falls
Sheboygan Falls Vacation Rentals
Kohler
Kohler Vacation Rentals
Mitchell
Mitchell Vacation Rentals
Oostburg
Oostburg Vacation Rentals
More Places to Stay Near Sheboygan County

Sheboygan County Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Visit During the Off-Peak Season: Scheduling your stay outside of busy holidays ensures a more relaxed experience and better access to local attractions in this scenic destination.
  • Explore Local Dining Options: Take advantage of the region’s renowned eateries to enjoy authentic flavors while supporting small businesses during your trip.
  • Utilize Waterway Access: Make the most of the area's lakes and waterways by engaging in water activities, which are perfect for both relaxation and adventure.
  • Book Your Accommodation Early: Secure your preferred vacation rentals well in advance to guarantee availability and to choose the best properties here that suit your travel needs.

Transportation Options

  • Sheboygan County Transportation Services: You can take advantage of local bus services that connect key towns and attractions within the area, offering a convenient way to explore without a car.
  • Rental Car Services: Numerous rental agencies operate here, providing the flexibility to explore at your own pace while enjoying the scenic views of this destination.
  • Taxi and Ride-Sharing Options: Taxis and ride-sharing services like Uber and Lyft are available for quick, reliable transportation around the region, especially for short trips or late-night outings.
  • Regional Airport Access: The area is served by nearby airports, making it easy to reach your vacation rentals from across the country with minimal hassle.

Local Customs Options

  • Polka Music Tradition: Embrace the lively polka music that is a cherished part of local festivities and cultural gatherings here, reflecting the area's rich European heritage.
  • Seafood Cuisine Etiquette: Enjoy the region’s renowned fresh fish, especially during local festivals, where traditional dining customs emphasize community and shared meals.
  • Harbor and Maritime Customs: Respect the maritime traditions by observing local practices at the waterfront, highlighting the area's deep connection to boating and fishing industries.
  • Agricultural Celebrations: Participate in seasonal festivals that celebrate farming and harvest traditions, showcasing the area's strong agricultural roots and community spirit.

Frequently Asked Questions About Sheboygan County?

1. What are the top vacation rentals in Sheboygan County?

There are a lot of options in Sheboygan County. If you plan on staying in the Sheboygan County 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 County:

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

There are 13 vacation rentals with private pools near Sheboygan County. Top-rated RBO homes that have access to a swimming pool include:

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

If you are looking for a family-friendly vacation home in Sheboygan County, 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 County:

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 565 in the Sheboygan County 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 County. 

5. What is the cancellation policy for a vacation rental in Sheboygan County?

The cancellation policy varies depending on the property listing. You should review the specific cancellation terms listed for your selected rental to understand whether you can get a full, partial, or no refund if you need to cancel.

6. How do I contact the host or owner of a vacation rental in the area for special requests?

You can reach out directly to the host or property owner through the messaging feature provided on the booking platform. This allows you to inquire about any special requests or additional information needed before confirming your reservation.

7. Are there any age restrictions or requirements when booking a vacation rental here?

Age restrictions and requirements are set by individual property owners. You should check the listing details or contact the host directly to confirm if there are any minimum age limits or other eligibility criteria.

8. What amenities are typically included in vacation rentals in this destination?

Amenities vary by property, but common features include Wi-Fi, kitchen facilities, parking, and outdoor spaces. To get detailed information about what is included, review the property listing or contact the owner directly.

9. Is it possible to extend my stay at a vacation rental in Sheboygan County, and how do I do so?

Extension options depend on the availability of the property and the owner's policies. You should contact the host as early as possible through the platform to request an extension and confirm whether it can be accommodated.

Sheboygan County Top Rated Vacation Rentals

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