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  3. Monticello
  4. Rentals by Owner

Discover Your Perfect Monticello Rentals by Owner

Monticello Rentals by Owner

More Top-Rated Rentals by Owner in Monticello Area

Why Choose Rent By Owner for your Monticello 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 Monticello

When should you plan your Rentals by Owner stay?

To make the most of your stay in this charming area, consider visiting during the seasons when local events and weather conditions align perfectly with your vacation preferences, ensuring a memorable and enjoyable experience at your rental by owner in Monticello, Wisconsin.

Peak Season Highlights

summer
Summer (June to August)

During the warm summer months, you'll experience vibrant outdoor activities and scenic views that showcase this destination at its best. The area is lively, making it ideal for those seeking a bustling atmosphere and plenty of daytime sunshine.

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

Autumn offers stunning foliage and comfortable weather, attracting visitors who want to enjoy scenic drives and outdoor exploration in this region. The crisp air and colorful landscapes create an inviting setting for a memorable stay.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F

Off-Season Highlights

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Winter (December to February)

The quieter winter months provide a peaceful retreat with fewer visitors, perfect for relaxing indoors or enjoying the tranquility of the snowy landscape. This season appeals to travelers seeking solitude and cozy accommodations.

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

As nature begins to awaken, this period features blooming flora and milder temperatures, offering a quieter time to explore the area's natural beauty. It’s an ideal season for those wanting to avoid peak crowds while still enjoying pleasant weather.

Average Temperature Daytime: 50°F to 60°F - Nighttime: 30°F to 40°F

Weekly Weather Forecast for Monticello

How to Book Your Monticello 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 Monticello

More Top-Rated Rentals by Owner in Monticello 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

  • Access to spacious outdoor patios or decks for relaxing and entertaining
  • Beautifully maintained gardens or landscaped yards to enjoy the natural surroundings
  • Convenient parking areas with ample space for your vehicle
  • Outdoor dining options, such as picnic tables or barbecue grills
  • Private or shared waterfront access, perfect for lakeside activities
  • Easy-to-use outdoor fire pits for cozy evenings under the stars
  • Designed spaces for outdoor recreation, including walking trails or yard games

Top Attractions Around Monticello

What attractions are nearby?

Within this charming region, you can enjoy a variety of outdoor activities and local attractions that showcase the natural beauty and welcoming community nearby your rental by owner.

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Family Activities

  • Plum Lake Recreation Area: Enjoy family picnics, fishing, and outdoor activities at this scenic spot nestled near the area, perfect for a relaxing day out with loved ones.
  • Local Nature Trails: Explore the region’s natural beauty by hiking or biking along well-maintained trails that showcase the area's lush landscapes and wildlife.
  • Community Events and Festivals: Participate in seasonal festivals and community gatherings hosted here, offering fun entertainment and cultural experiences for all ages.
  • Family-Friendly Parks: Spend quality time at nearby parks equipped with playgrounds and open spaces, ideal for children to play and families to unwind together.
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Adult Activities

  • Exploring the Local Wineries: Discover the region's renowned wineries, where you can enjoy tastings and tours that highlight the area's rich winemaking heritage.
  • Golfing at Scenic Courses: Tee off at nearby golf courses offering stunning views of the surrounding landscape, providing the perfect setting for a relaxing day on the greens.
  • Participating in Regional Festivals: Engage in seasonal festivals and community events that showcase local culture, crafts, and cuisine unique to this destination.
  • Enjoying Nature Trails and Parks: Take advantage of well-maintained trails and parks to hike, bike, or simply unwind amidst the peaceful scenery of the area.

Monticello Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead for the Region's Seasons: Scheduling your visit during the region's peak seasons ensures you experience the best weather and activities while making the most of your rental stay.
  • Explore Local Dining Options: Take advantage of nearby eateries to savor regional flavors that enhance your overall experience in this area.
  • Utilize Nature Trails and Outdoor Spaces: Make the most of the scenic surroundings by exploring local trails and outdoor areas accessible from your rental.
  • Connect with Community Events: Check out seasonal events or local gatherings to immerse yourself more deeply into the area's culture during your visit.

Transportation Options

  • Local Bus Services: The area is served by regional bus routes that offer convenient transportation options for getting around Monticello and exploring the surrounding region.
  • Rental Car Agencies: Several rental car agencies are available nearby, providing flexible travel solutions for visitors who prefer driving themselves during their stay.
  • Taxi and Ride-Sharing Services: Taxis and ride-sharing options like Uber and Lyft are accessible here, allowing you to quickly reach local attractions or your rental accommodations with ease.
  • Private Shuttle Services: Private shuttle services operate in this destination, offering tailored transportation for groups or guests seeking a comfortable, hassle-free journey around town.

Local Customs Options

  • Welcoming Local Hospitality: Embrace the friendly and warm attitude of residents, who take pride in sharing their Midwestern hospitality with visitors exploring this charming area.
  • Respect for Outdoor Traditions: Participate in outdoor activities with an appreciation for the region's strong community focus on conservation and nature preservation.
  • Engagement in Seasonal Celebrations: Experience the area's local festivals and seasonal events that reflect its rich agricultural roots and cultural heritage.
  • Honoring Agricultural Practices: Observe and respect the traditional farming customs that remain integral to the local lifestyle here, emphasizing sustainability and community involvement.

Frequently Asked Questions About Monticello Rentals by Owner

1. What are the top vacation rentals in Monticello?

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

2. How many Rentbyowner vacation rentals are available in Monticello?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 35 in the Monticello 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 Monticello. 

3. What is the cancellation policy for rental properties in this area?

Cancellation policies vary by listing. To ensure you understand the specific terms, please review the cancellation section on the property’s page or contact the owner directly before booking.

4. How do I communicate with the property owner before booking?

You can send an inquiry through the booking platform to ask questions or clarify details. Owners are typically responsive and can provide additional information about their rental in this region.

5. Are there any house rules I should be aware of when staying here?

Every rental has its own set of house rules detailed in the listing. Be sure to read these carefully before confirming your reservation to ensure a smooth stay in this area.

6. Is a security deposit required, and how is it handled?

Many owners request a security deposit to cover potential damages. The specifics, including amount and payment process, are listed on each property’s page. Contact the owner for clarification if needed.

7. What amenities are included in the rental properties here?

Amenities vary by listing, but common features include Wi-Fi, parking, and kitchen facilities. Review the property's description thoroughly or reach out to the owner to confirm the amenities available during your stay.

More Rentals You May Like Near Monticello

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More Top-Rated Rentals by Owner in Monticello Area