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  2. Wisconsin
  3. Ashland
  4. Rentals by Owner

Ashland Rentals by Owner

|
9.6 (56 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pet Friendly
|
9.6 (97 Reviews)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Why Choose Rent By Owner for your Ashland 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 Ashland

When should you plan your Rentals by Owner stay?

Choosing the optimal time to vacation here can enhance your experience, allowing you to enjoy the area's natural beauty and local events while making the most of your rental by owner in Ashland, Wisconsin.

Peak Season Highlights

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Summer (June to August)

During the peak summer months, you'll enjoy warm temperatures and longer daylight hours, making it ideal for exploring the scenic beauty of the region. This time attracts visitors seeking outdoor activities and vibrant community events in Ashland.

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

Autumn brings colorful foliage and crisp air, drawing travelers who want to experience the area's natural beauty and seasonal events. Expect lively local gatherings as the region showcases its stunning fall scenery.

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 winter months offer a quieter atmosphere with colder temperatures, perfect for those seeking a peaceful retreat or winter sports opportunities. The region transforms into a serene winter wonderland during this off-peak period.

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

Spring ushers in milder weather and blooming landscapes, making it an excellent time for quieter visits and enjoying the budding scenery before the busy summer season begins. Fewer crowds make this an appealing choice for relaxed getaways.

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

Weekly Weather Forecast for Ashland

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

  • Enjoy outdoor dining areas perfect for summer evenings in the region's scenic surroundings.
  • Take advantage of private patios or decks to relax and soak in the natural beauty nearby.
  • Explore spacious yards or gardens that offer space for outdoor activities and gatherings.
  • Make the most of fire pits or outdoor fireplaces to cozy up during cooler evenings.
  • Access scenic walking trails or pathways directly from your rental for outdoor adventures.
  • Benefit from outdoor seating areas designed for enjoying the fresh air and views of the area.
  • Utilize community or private docks if available, offering direct access to local lakes or rivers here.
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Family Activities

  • Amethyst Mine Panorama: Explore this family-friendly attraction where you can search for your own amethyst gemstones, creating lasting memories and unique souvenirs in the region.
  • Ashland Marina Park: Enjoy a relaxing day by the water at the marina park, perfect for picnicking, fishing, or watching boats glide across the bay with your loved ones.
  • Bayfield County Fairgrounds: Experience local festivities and events throughout the year that offer engaging activities for children and families alike in this scenic area.
  • Tom Rileys Old Fire Hall and Museum: Discover local history through interactive exhibits suitable for all ages, providing an educational glimpse into the area's past.
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Adult Activities

  • Exploring the Ashland Waterfront: You can enjoy leisurely strolls along the shoreline, taking in scenic views of Lake Superior while appreciating the tranquil atmosphere.
  • Visiting the Northland College Campus: This destination offers an enriching experience with its beautiful grounds and opportunities to engage with local art and cultural exhibits.
  • Discovering the Bayfield Peninsula Trails: Perfect for outdoor enthusiasts, these trails provide scenic routes for hiking, biking, and experiencing nature's serenity in the region.
  • Enjoying Local Dining Experiences: The area boasts a variety of restaurants featuring fresh, locally sourced ingredients, ideal for savoring regional flavors after a day of adventures.

Other Places to Stay in Ashland, WI

Northern Great Lakes Visitor Center
Ashland Historical Museum
Maslowski Beach
White River
Chequamegon Bay Golf Course

Ashland Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Events and Festivals: Check out the region’s calendar for seasonal events to immerse yourself in the local culture during your stay.
  • Enjoy Outdoor Activities: Make the most of nearby parks and natural areas by planning outdoor adventures that highlight this destination’s scenic beauty.
  • Research Dining Options: Discover highly-rated eateries and hidden gems in the area to experience authentic regional cuisine.
  • Utilize Personalized Recommendations: Connect with property owners or locals for tailored suggestions on must-visit spots to enhance your visit here.

Transportation Options

  • Car Rentals: Renting a car provides you with the flexibility to explore the surrounding region at your own pace while staying centrally located here.
  • Local Taxis and Rideshare Services: Convenient for quick trips within town or traveling to nearby attractions, these options ensure reliable transportation in the area.
  • Bike Rentals: For an eco-friendly and scenic way to experience this destination, bike rentals are readily available for exploring local sights and trails.
  • Public Transit: Though limited, the regional bus services offer an affordable means of transportation around here if you prefer not to drive.

Local Customs Options

  • Respect for the Indigenous Heritage: You’ll find that honoring local Native American traditions and history is an important part of the area’s customs here in Ashland, Wisconsin.
  • Community Celebrations: Participating in seasonal festivals and gatherings reflects the region's close-knit spirit and love for celebrating local culture.
  • Environmental Stewardship: Maintaining a respectful attitude towards the natural surroundings exemplifies how locals cherish their pristine lakes and forests.
  • Traditional Outdoor Etiquette: When exploring here, it’s customary to follow guidelines that preserve the wilderness and ensure enjoyable experiences for everyone.

Frequently Asked Questions About Ashland Rentals by Owner

1. How many Rentbyowner vacation rentals are available in Ashland?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 23 in the Ashland 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 Ashland. 

2. What is the cancellation policy for a rental by owner in Ashland, Wisconsin?

The cancellation policy varies depending on the individual listing. You should review the specific rental's terms on the listing page or contact the owner directly to understand their policies regarding cancellations and refunds.

3. How do I ensure the rental property in Ashland meets my needs before booking?

You can review detailed descriptions, photos, and amenities listed on the property page. If you have specific questions or requirements, reaching out to the owner can help confirm that the rental aligns with your expectations.

4. Are there any additional fees when booking a rental by owner in this area?

Additional fees such as cleaning fees, service charges, or taxes are typically outlined in the listing details. It’s recommended to read through the full description or ask the owner about any extra costs involved before completing your booking.

5. What is the check-in and check-out process for rentals in this destination?

Check-in and check-out procedures vary per property. Details are usually provided in the listing or communicated directly by the owner. Contacting the owner beforehand ensures a smooth arrival and departure experience.

6. How can I contact the owner if I have questions about my stay in this region?

You can reach out to the property owner through the messaging system provided on the booking platform. This allows you to clarify details about the rental and ensure all your concerns are addressed prior to your stay.

More Rentals You May Like Near Ashland

4.0 (1 Review)
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