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  3. Baileys Harbor
  4. Rentals by Owner

Discover Your Perfect Baileys Harbor Rentals by Owner

Baileys Harbor Rentals by Owner

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SHD4720
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Why Choose Rent By Owner for your Baileys Harbor 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 Baileys Harbor

When should you plan your Rentals by Owner stay?

Choosing the optimal time to vacation here can enhance your experience and ensure access to the best rental options available through Rent By Owner in this charming area of Wisconsin.

Peak Season Highlights

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Summer (June to August)

During the summer months, this destination experiences its busiest period, with visitors enjoying warm weather and extended daylight. It's an ideal time for outdoor activities and exploring the scenic beauty of the region.

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

Autumn ushers in a vibrant display of fall foliage, attracting travelers interested in scenic drives and nature walks. This is when the area’s natural beauty truly shines, making it a popular season for visiting.

Average Temperature Daytime: around 65°F to 70°F - Nighttime: around 50°F to 55°F

Off-Season Highlights

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Winter (November to February)

The winter months see fewer visitors, offering a quiet retreat for those seeking tranquility and a cozy atmosphere. The region may experience snowfall, adding to its serene charm during this time.

Average Temperature Daytime: around 30°F to 40°F - Nighttime: around 15°F to 25°F
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Spring (March to May)

Early spring marks the transition into warmer weather, with fewer tourists around. It’s a peaceful period perfect for enjoying the budding scenery and avoiding peak crowds.

Average Temperature Daytime: around 45°F to 55°F - Nighttime: around 35°F to 40°F

Weekly Weather Forecast for Baileys Harbor

How to Book Your Baileys Harbor 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 Baileys Harbor

More Top-Rated Rentals by Owner in Baileys Harbor 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 dining areas with picnic tables to savor meals alfresco amidst the scenic surroundings.
  • Take advantage of a private or shared fire pit for cozy evenings under the stars.
  • Relax by a spacious yard or lawn area ideal for outdoor games and family activities.
  • Make use of community or private boat docks if you're interested in exploring local waterways.
  • Utilize outdoor grills provided for barbecuing during your stay in this charming region.
  • Find comfortable lounge chairs perfect for sunbathing or reading outdoors.
  • Discover easy access to walking trails, biking paths, or nature preserves nearby for outdoor adventures.

Top Attractions Around Baileys Harbor

What attractions are nearby?

In this charming area, you can enjoy a variety of outdoor activities such as exploring scenic hiking trails, relaxing by tranquil lakes, or discovering local wildlife, making it an ideal destination for nature enthusiasts staying in nearby rental accommodations.

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Family Activities

  • Baileys Harbor Marine Museum: Explore local maritime history through engaging exhibits that captivate all ages in this charming region.
  • Horseshoe Bay Farms: Discover family-friendly activities at a working farm where you can enjoy guided tours, petting areas, and scenic countryside views.
  • Peninsula State Park: Experience the great outdoors with hiking, picnicking, and biking amidst stunning natural scenery on this popular destination in the area.
  • Fish Creek:**: Wander through this quaint nearby town to enjoy local shops, waterfront dining, and leisurely strolls along scenic harbor areas suited for families.
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Adult Activities

  • Scenic Kayaking Tours: Explore the calm waters around this charming region by kayak, offering a peaceful way to enjoy the area's natural beauty.
  • Bird Watching Excursions: Visit local wildlife refuges and protected areas where you can observe diverse bird species in their natural habitat.
  • Wine Tasting Experiences: Sample regional wines at nearby vineyards that showcase the area's burgeoning wine scene and local craftsmanship.
  • Historic Lighthouse Visits: Discover the rich maritime history by touring iconic lighthouses that overlook the region’s picturesque shoreline.

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Baileys Harbor Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Nature Trails: Take advantage of the area’s scenic trails to enjoy the natural beauty and tranquility that make this destination a perfect retreat.
  • Book Early for Popular Rentals: Secure your preferred rental by owner early to ensure access to the best accommodations in this region.
  • Visit During Off-Peak Seasons: Consider planning your visit during less busy times to experience quieter surroundings and more personalized service.
  • Utilize Local Resources: Connect with local visitor centers or hosts to discover hidden gems and tips for making the most of your stay here.

Transportation Options

  • Personal Vehicles: Renting a car is a convenient way to explore this scenic region and access your rental property with ease.
  • Public Transit: The local bus services provide affordable transportation options for getting around the area and nearby attractions.
  • Taxis and Rideshare Services: Available throughout the region, these services offer quick and reliable transportation directly to your vacation rental or destination.
  • Bicycle Rentals: For an environmentally friendly and leisurely way to enjoy the area's natural beauty, bike rentals are readily accessible here.

Local Customs Options

  • Community Fish Boil Tradition: Participating in or observing the local fish boil provides a genuine taste of regional hospitality and culinary customs here.
  • Respect for Lake Life: Embracing outdoor etiquette by respecting the area's lakes and waterways enhances your connection with this scenic region.
  • Support for Local Artisans: Exploring the work of local craftsmen and artists helps you appreciate the region's vibrant creative heritage.
  • Celebration of Seasonal Festivals: Attending seasonal gatherings allows visitors to experience the area's unique cultural traditions firsthand.

Frequently Asked Questions About Baileys Harbor Rentals by Owner

1. What are the top vacation rentals in Baileys Harbor?

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

2. How many Rentbyowner vacation rentals are available in Baileys Harbor?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 141 in the Baileys Harbor 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 Baileys Harbor. 

3. What is the cancellation policy for rental properties in Baileys Harbor?

Cancellation policies vary by individual owner. You should review the specific rental listing details or contact the owner directly to understand the terms related to cancellations and potential refunds.

4. How do I verify the safety and cleanliness standards of a rental in this region?

Details about safety measures and cleanliness protocols are typically included in the property listing. For additional assurance, reach out to the owner to inquire about their cleaning procedures and safety features.

5. Are there any specific check-in or check-out times I should be aware of in Baileys Harbor rentals?

Check-in and check-out times are set by each property owner. These details are provided in the listing, but contacting the owner can help clarify any flexible timing options or special arrangements.

6. Can I request additional amenities or services during my stay?

Many owners are willing to accommodate special requests but please communicate your needs directly through the listing or prior to booking to confirm availability and any extra costs.

7. What should I know about the booking process for vacation rentals here?

Booking usually involves selecting your dates, reviewing the listing details, and confirming your reservation. For specific instructions or assistance, you can contact the owner or utilize the platform’s support resources to ensure a smooth booking experience.

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More Top-Rated Rentals by Owner in Baileys Harbor Area