1. USA
  2. Wisconsin
  3. Sheboygan
  4. Road America
  5. Rentals by Owner

Discover Your Perfect Road America Rentals by Owner

Road America Rentals by Owner

More Top-Rated Rentals by Owner in Road America Area

Why Choose Rent By Owner for your Road America vacation rental?

What makes our Rentals by Owner 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 Road America

When should you plan your Rentals by Owner stay?

Choosing the optimal time to vacation here ensures you can fully enjoy the region’s vibrant atmosphere and available rental options, making your stay in Plymouth both memorable and hassle-free.

Peak Season Highlights

summer
Summer (June to August)

This is the most popular time to visit, as the region experiences warm weather and long daylight hours perfect for outdoor activities and enjoying the local scenery.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
autumn
Fall (September to November)

During this season, the area boasts vibrant fall foliage, making it an ideal time for scenic drives and outdoor exploration while the weather remains mild.

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

Off-Season Highlights

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Winter (December to February)

The cold winter months see fewer visitors, offering a quieter experience for those seeking tranquility amid occasional snowfall and crisp air.

Average Temperature Daytime: 20°F to 35°F - Nighttime: 10°F to 20°F
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Spring (March to May)

Early spring brings less crowds and a peaceful atmosphere, with nature gradually waking up and temperatures starting to warm.

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

Weekly Weather Forecast for Road America

How to Book Your Road America vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. 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 Road America

More Top-Rated Rentals by Owner in Road America Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner 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 seating areas such as patios or decks to relax and take in the scenic surroundings.
  • Benefit from private gardens or landscaped yards ideal for outdoor activities or casual gatherings.
  • Take advantage of on-site grilling facilities, perfect for enjoying outdoor meals with family and friends.
  • Discover spacious lawns or open fields suitable for outdoor games and recreational activities.
  • Utilize community outdoor pools or hot tubs if available within the rental complex, providing a refreshing break after exploring the region.
  • Make use of covered porches or verandas that offer shaded spots to unwind in the fresh air.
  • Access nearby parks or green spaces, providing additional outdoor adventures during your stay in this area.

Top Attractions Around Road America

What attractions are nearby?

In this area, you can explore a variety of outdoor activities and local attractions that showcase the region’s natural beauty and vibrant community, making your stay in Plymouth both enjoyable and memorable.

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Family Activities

  • Plymouth Chamber of Commerce Museum: Discover local history and exhibits that offer an engaging experience for families interested in the area's heritage.
  • Plymouth Recreation Park: Enjoy outdoor fun with playgrounds, sports fields, and picnic areas perfect for family gatherings amid natural surroundings.
  • Fox Hills Resort Golf Course: Introduce your family to a scenic round of golf at this nearby course, offering beautiful views and beginner-friendly options.
  • Fishing on the Fox River: Spend quality time casting lines and relaxing along the tranquil waters, ideal for families seeking outdoor adventure in the region.
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Adult Activities

  • Wine Tasting Tours: Discover local wineries in the area and enjoy guided tastings that showcase Wisconsin’s regional wines.
  • Northern Lake Cruises: Experience scenic boat cruises on nearby lakes, offering a relaxing way to view the region’s natural beauty.
  • Golfing Adventures: Play a round at championship golf courses that are renowned for their well-maintained fairways and picturesque settings.
  • Nature Hikes and Trails: Explore the surrounding nature preserves and trails, perfect for outdoor enthusiasts seeking tranquility and scenic views.

Road America Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Visit Around Events: Check the local event calendar to align your stay with exciting races or festivals at Road America, enhancing your experience in this vibrant region.
  • Choose Strategic Accommodation: Opt for rentals close to the racecourse to minimize travel time and maximize your time enjoying the lively atmosphere of the area.
  • Explore Local Dining Options: Take advantage of nearby eateries offering regional specialties, allowing you to savor the authentic flavors that make this destination unique.
  • Utilize Nearby Recreation Opportunities: Discover outdoor activities and scenic spots around Plymouth that complement your racing adventures and enrich your stay here.

Transportation Options

  • Car Rentals: You can easily rent a vehicle locally to explore the region surrounding Road America in Plymouth, Wisconsin, ensuring flexible travel options during your stay.
  • Public Transportation: The area offers bus services and regional transit options that connect you to nearby towns and attractions with convenience.
  • Taxi and Ride-Sharing Services: Reliable taxi and ride-sharing providers are available here, providing a convenient way to get around without the need for personal transportation.
  • Bicycle Rentals: For those seeking an eco-friendly option, bicycle rentals are accessible locally, allowing you to enjoy scenic rides through the region's picturesque landscapes.

Local Customs Options

  • Respect for Local Racing Culture: Here, it’s customary to show enthusiasm and support during race events at Road America, reflecting the area's passion for motor sports.
  • Community Celebrations: Participating in regional festivals and gatherings offers a wonderful way to embrace local traditions and meet residents of this vibrant region.
  • Environmental Consciousness: Maintaining cleanliness and respecting natural surroundings are valued practices in this area, ensuring the scenic beauty remains unspoiled for visitors and locals alike.
  • Traditional Wisconsin Hospitality: Visitors often experience warm welcomes and friendly interactions that highlight the genuine hospitality characteristic of this destination.

Frequently Asked Questions About Road America Rentals by Owner

1. What are the top vacation rentals in Road America?

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

2. How many Rentbyowner vacation rentals are available in Road America?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 123 in the Road America 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 Road America. 

3. What is the cancellation policy for rental properties by owner near Road America in Plymouth, Wisconsin?

Cancellation policies vary depending on the individual listing. You should review each property's specific policy on the listing page or contact the owner directly to understand the terms and any applicable fees.

4. How do I secure my booking at a vacation rental near this racing destination?

Bookings are typically secured through the platform by submitting a reservation request and making a payment. Be sure to read the listing details and communicate with the owner if you have any questions before confirming your reservation.

5. Are there any additional fees or deposits required when booking an owner-operated rental in the region?

Additional fees, such as cleaning fees or security deposits, are often specified on the listing. You should check the detailed listing information or contact the owner directly to clarify all charges before completing your booking.

6. What amenities are usually included in rental homes near Road America?

Amenities vary by property but commonly include essentials like Wi-Fi, parking, and kitchen facilities. For specific features, review each listing carefully or reach out to the owner to ensure the rental meets your needs.

7. What is the best way to contact the owner of a rental in this destination for special requests or questions?

You can contact the owner directly through the messaging system provided by the booking platform. It's recommended to communicate your inquiries or special requests before finalizing your reservation to confirm availability and arrangements.

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