Discover Your Perfect Road America Vacation Homes

Best Vacation Homes in Road America

Why Choose Rent By Owner for your Road America 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 Road America

When should you plan your Vacation Rentals stay?

Timing your visit to this destination can greatly enhance your experience, so consider planning your trip during the most favorable seasons when the region offers ideal weather and local events that complement your stay in Road America.

Peak Season Highlights

summer
Summer (June to August)

During the summer months, this destination experiences its peak tourist season, making it ideal for enjoying outdoor activities and lively events around the region.

Average Temperature Daytime: around 80°F (27°C) - Nighttime: around 60°F (16°C)
autumn
Fall (September to November)

The fall season attracts visitors with its scenic foliage and pleasant weather, perfect for exploring the area's natural beauty and local festivities.

Average Temperature Daytime: around 65°F (18°C) - Nighttime: around 45°F (7°C)

Off-Season Highlights

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Winter (December to February)

During winter, fewer travelers visit, offering a quieter experience in the area—an excellent time for peaceful getaways and cozy accommodations.

Average Temperature Daytime: around 30°F (-1°C) - Nighttime: around 15°F (-9°C)
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Spring (March to May)

In spring, visiting here means enjoying the early blooms and milder weather while avoiding the crowds typical of the peak seasons.

Average Temperature Daytime: around 55°F (13°C) - Nighttime: around 35°F (2°C)

Weekly Weather Forecast for Road America

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.

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

  • You can enjoy outdoor seating areas to relax and take in the scenic views of the region.
  • Many properties offer BBQ grills, perfect for preparing meals during your stay here.
  • Expect well-maintained gardens or landscaped yards that add to the outdoor appeal.
  • Some rentals provide access to private patios or decks for outdoor dining and lounging.
  • There are often fire pits available for cozy evenings with family or friends.
  • The area frequently features spacious parking spaces suitable for boats or RVs if needed.
  • Look for amenities like outdoor sports courts or lawns for recreational activities during your visit.
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Family Activities

  • Road America Driving Experience: Enjoy an exhilarating day at this renowned race track by witnessing high-speed races and even taking part in driving classes suitable for the whole family.
  • Plymouth Historical Museum Tour: Discover the area's rich history through engaging exhibits and interactive displays that educate and entertain visitors of all ages.
  • Lakeside Recreation Activities: Spend quality time outdoors by participating in fishing, boating, or picnicking along the scenic lakes surrounding this region.
  • Family-Friendly Festivals and Events: Check out local festivals held throughout the year that feature live entertainment, food vendors, and activities perfect for children and adults alike.
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Adult Activities

  • Watch Thrilling Race Events: Experience the excitement of race weekends at Road America, where high-speed competitions are a highlight for motorsport enthusiasts visiting the region.
  • Explore Local Wineries: Enjoy wine tasting tours at nearby Wisconsin wineries, offering a perfect blend of local flavors and scenic vineyard views in this area.
  • Visit Historic Plymouth Downtown: Stroll through the charming downtown district to discover unique shops, authentic eateries, and historic landmarks that reflect the region’s heritage.
  • Relax at Scenic Lakeside Parks: Unwind by the water at nearby parks with opportunities for picnicking, fishing, and enjoying nature amidst this inviting Wisconsin landscape.

Road America Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local events and festivals: Take advantage of the area’s vibrant community gatherings to immerse yourself in local culture and enjoy additional entertainment during your stay.
  • Choose a central vacation rental: Opt for accommodations that are conveniently located near the main attractions and amenities to maximize your time here.
  • Plan outdoor activities early: The region offers beautiful outdoor scenery, so scheduling activities like cycling or scenic drives during daylight hours helps you make the most of nature's offerings.
  • Check for seasonal promotions: Keep an eye out for special deals and discounts on vacation rentals, which can enhance your experience in this destination while offering great value.

Transportation Options

  • Car Rentals: You can easily rent a vehicle in the area to explore the region at your own pace and enjoy flexible transportation options during your stay.
  • Public Transit: Buses and local transit services provide convenient access around the destination, making it simple to reach key spots without a personal vehicle.
  • Taxi Services: Reliable taxi companies operate throughout the region, offering quick and comfortable rides directly from your vacation rental or other points of interest.
  • Rideshare Options: Popular rideshare platforms are available here, providing an easy way to get around while enjoying the comfort and safety they offer.

Local Customs Options

  • Strawberry Festival Celebrations: You can immerse yourself in the local tradition of celebrating Wisconsin's rich agricultural heritage during the region’s annual strawberry festival, featuring community gatherings and seasonal produce.
  • Plymouth Downtown Parades: Expect lively parades through the historic downtown area, showcasing local bands, marching groups, and vibrant floats that embody the area's welcoming spirit.
  • Folk Music Gatherings: The community often comes together to enjoy traditional folk music performances, reflecting the region's cultural roots and fostering a strong sense of local pride.
  • Farmers Market Exchange: Visiting the local farmers market allows you to experience the region's farm-to-table customs, offering fresh produce and handcrafted goods from nearby farms.

Frequently Asked Questions About 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 147 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 vacation rentals near Road America in Plymouth, Wisconsin?

The cancellation policy varies depending on the specific property you choose to book. It is recommended to review the details listed on the property’s page or contact the owner directly for accurate information regarding cancellations.

4. Are there any specific check-in and check-out times I should be aware of when booking a vacation rental near Plymouth?

Check-in and check-out times are set by each individual property owner. You can find these details in the listing description or by reaching out directly to the host for clarification.

5. How do I ensure my reservation in this area is secure and reliable?

Reservations are processed through a trusted platform that offers secure payment options. For added peace of mind, always verify the property details and communicate with the owner before confirming your booking.

6. Are pet-friendly vacation rentals available near Road America, and what are the policies for bringing pets?

Some properties may accept pets, but pet policies differ from one listing to another. Review the specific pet policy and fees listed on the property details or contact the owner for confirmation.

7. What amenities and features should I expect from vacation rentals in this region?

Amenities vary depending on the property, but many offer essentials such as Wi-Fi, parking, and fully equipped kitchens. Be sure to check the individual listing for a complete list of amenities before booking.

Best Vacation Homes in Road America