Highland Rentals by Owner
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Why Choose Rent By Owner for your Highland vacation rental?
What makes our Rentals by Owner special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Highland
When should you plan your Rentals by Owner stay?
Choosing the ideal time to vacation here can enhance your experience, as each season offers unique opportunities to enjoy all that Highland has to offer while making the most of your rental by owner arrangements through Rent By Owner.
Peak Season Highlights
Summer (June to August)
During the peak summer months, you can enjoy warm daytime temperatures and a lively atmosphere in this destination. It’s an ideal time for outdoor activities and exploring the scenic beauty of the region.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
Fall (September to November)
Autumn brings stunning fall foliage and pleasant weather, making it a popular season for visitors seeking outdoor adventures and picturesque views. The region is vibrant with seasonal colors and cooler evenings.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
Off-Season Highlights
Winter (December to February)
The winter months offer a quieter experience with colder temperatures and fewer visitors. It's a great time for cozy stays and enjoying the tranquility of the area.
Average Temperature Daytime: 20°F to 35°F - Nighttime: 10°F to 20°F
Spring (March to May)
Springtime welcomes milder weather and blooming landscapes, providing a peaceful atmosphere for those looking to avoid the crowds. The region begins to wake up with fresh energy and greenery.
Average Temperature Daytime: 50°F to 60°F - Nighttime: 35°F to 45°F
Weekly Weather Forecast for Highland
How to Book Your Highland 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 Highland
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
- You can enjoy a private outdoor space with a patio or deck to unwind and soak up the natural surroundings.
- Many rentals offer access to scenic hiking trails directly from your doorstep, perfect for exploring the region's outdoor beauty.
- Look for properties with a fire pit area where you can gather around and enjoy evenings under the stars.
- Expect outdoor dining areas, such as picnic tables or BBQ grills, ideal for alfresco meals in this outdoor-focused destination.
- Some rentals include a spacious yard or lawn, great for outdoor activities or relaxing in a peaceful environment.
- Convenient access to nearby lakes or rivers often means you can take advantage of fishing, canoeing, or kayaking during your stay.
- Many properties feature outdoor seating areas designed for enjoying the fresh air and scenic views of this outdoor haven.
Top Attractions Around Highland
What attractions are nearby?
While staying here, you can enjoy nearby outdoor activities such as hiking, fishing, and exploring scenic trails in the surrounding region of Highland, Wisconsin, USA, making it a perfect destination for nature enthusiasts seeking a memorable experience.
Family Activities
- Highland Family Fun Day: Participate in this lively event that offers entertainment and activities suitable for children and parents alike, making it a perfect outing for your family.
- Local Nature Trails: Explore scenic hiking and biking trails in the area that provide an engaging outdoor adventure for families seeking to enjoy the region's natural beauty.
- Community Parks and Playgrounds: Spend quality time at well-maintained parks with playgrounds and picnic areas, ideal for relaxing family afternoons in the area.
- Seasonal Festivals: Experience local festivals featuring kid-friendly activities, crafts, and entertainment, giving your family a taste of regional culture and fun.
Adult Activities
- Exploring local vineyards: You can enjoy wine tasting tours at nearby vineyards, immersing yourself in the region’s renowned wine culture and scenic vineyard vistas.
- Hiking and nature walks: Discover the area's natural beauty by hiking along well-maintained trails that offer picturesque views and a peaceful outdoor experience.
- Fishing on nearby lakes: Spend your day casting lines in pristine lakes, where you can relax while trying to catch local freshwater fish species.
- Golfing at premier courses: Play on top-rated golf courses designed for all skill levels, providing both leisure and a challenge amidst beautiful scenery.
Other Places to Stay in Highland, WI
Highland Travel Tips
How Can You Make the Most of Your Stay?
- Explore local outdoor activities: Maximize your stay by taking advantage of the region’s scenic parks and natural areas for hiking, biking, or relaxing in nature.
- Connect with your host: Communicate directly with property owners to receive personalized recommendations and ensure a smooth check-in process.
- Plan ahead for seasonal events: Check the area’s calendar for local festivals or seasonal activities that can enrich your experience during your visit.
- Utilize nearby amenities: Take advantage of the region’s local shops and eateries to get a true taste of the destination’s unique flavor and hospitality.
Transportation Options
- Personal Vehicle Rentals: Renting a car here offers you the flexibility to explore the area and access your rental by owner accommodations with ease.
- Local Taxi Services: Taxis provide convenient transportation options for short trips within the region, ensuring you can reach nearby attractions comfortably.
- Public Transit Systems: Buses serve the broader area, giving you an affordable way to navigate this destination without the need for private transportation.
- Bike Rentals: For environmentally friendly travel and scenic exploration, bike rentals are available to help you enjoy the picturesque surroundings of the region.
Local Customs Options
- Traditional Wisconsin Gatherings: You might notice locals celebrating with hearty meals and community events that emphasize camaraderie, reflecting the area's rich social customs.
- Respect for Nature: Respect for the natural environment is a key part of life here, so be mindful of outdoor etiquette when exploring scenic areas around your rental.
- Local Craftsmanship: Supporting regional artisans by purchasing handmade crafts is appreciated and a common practice among residents during visits to local markets.
- Seasonal Celebrations: The region celebrates seasonal festivals that highlight its cultural heritage, offering authentic experiences during your stay.
Frequently Asked Questions About Highland Rentals by Owner
1. What are the top vacation rentals in Highland?
There are a lot of options in Highland. If you plan on staying in the Highland area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Highland:
- Stunning, serene, rustic house in the woods near Spring Green, Wisconsin
- Vermont West - Beautiful, Private, Serene Home Away from Home
- Amish-Built Cabin in the Driftless Area
- Elegant country retreat near Spring Green w expansive views of Driftless Region
- The Barn at Big Valley Ranch
- Newly remodeled log cabin next to beautiful Wisconsin River- Rivers Edge Cabin
- Rustic, Elegant 8,000 Sq. Ft. Timber Frame Lodge in Southwest Wisconsin.
- Private Isle-side, Waterfront Retreat with Stunning Views/Pet Friendly
- Enjoy peaceful surroundings
- Silver Birch Retreat. Spacious, pet friendly country home
2. How many Rentbyowner vacation rentals are available in Highland?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 31 in the Highland 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 Highland.
3. What is the cancellation policy for rental properties in Highland, Wisconsin?
Cancellation policies vary by individual listing. You should review the specific property’s cancellation terms on the listing page or contact the owner directly to understand your options and any applicable fees.
4. How do I contact the property owner before booking a rental in Highland, Wisconsin?
You can reach out to the property owner through the messaging system provided on the booking platform. This allows you to ask questions about the property, availability, and any special requests before making your reservation.
5. Are there any specific house rules I should be aware of when booking a rental in this region?
Yes, each rental has its own house rules outlined in the listing description. Be sure to read these carefully before confirming your reservation to ensure a smooth stay and compliance with the owner's guidelines.
6. How do I know if a rental property in Highland, Wisconsin is available for my travel dates?
Availability is displayed directly on the listing page for each property. If your preferred dates are shown as available, you can proceed with booking or contact the owner for further confirmation.
7. What amenities are generally included in rentals in Highland, Wisconsin, and how can I verify what's offered?
Amenities vary by property but typically include essentials like Wi-Fi, kitchen facilities, and parking. Details about specific amenities are listed on each rental’s page, and you can also message the owner for clarification or additional information.
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