Best Vacation Homes in Highland
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Highland Luxury Rentals
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Other
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Highland Pet Friendly Vacation Rentals
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Highland Large Vacation Homes
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Why Choose Rent By Owner for your Highland Vacation Rental Homes?
What makes our Vacation Rentals 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 Vacation Rentals stay?
Choosing the ideal time to visit ensures you can fully enjoy the peaceful beauty and outdoor activities that this destination has to offer, making your stay in Highland's vacation rentals truly memorable.
Peak Season Highlights
Summer (June to August)
During the summer months, you can enjoy warm weather and longer daylight hours that make outdoor activities more pleasant in this region.
Average Temperature Daytime: around 80°F - Nighttime: around 60°F
Fall (September to November)
Autumn brings stunning foliage and cooler temperatures, attracting visitors who want to experience vibrant landscapes and serene nature in the area.
Average Temperature Daytime: mid-60s°F - Nighttime: near 40°F
Off-Season Highlights
Winter (December to February)
In the winter, the region experiences colder weather with potential snow, offering a quiet and cozy escape for those seeking tranquility away from peak crowds.
Average Temperature Daytime: mid-30s°F - Nighttime: low 20s°F
Spring (March to May)
Early spring ushers in mild temperatures and blooming scenery, making it an ideal time for those looking for a peaceful retreat before the busy summer season begins.
Average Temperature Daytime: high 50s°F - Nighttime: mid-30s°F
Weekly Weather Forecast for Highland
How to Book Your Highland Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. 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 Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals 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 a private outdoor space with a spacious yard for relaxing or outdoor activities.
- Take advantage of a barbecue grill to host outdoor cookouts during your stay.
- Benefit from access to scenic patios or decks that provide stunning views of the surrounding nature.
- Make use of outdoor fire pits perfect for evening gatherings and marshmallow roasting.
- Explore nearby hiking trails and outdoor paths directly from your rental property.
- Utilize well-maintained outdoor seating areas designed for leisure and socializing.
- Have access to outdoor recreational equipment such as kayaks, paddleboards, or bicycles, ideal for exploring the local landscape.
Top Attractions Around Highland
What attractions are nearby?
While staying here, you can enjoy a variety of outdoor activities nearby, including scenic hikes, lakeside fishing, and peaceful nature walks that showcase the area's natural beauty.
Family Activities
- Highland Nature Preserve: Explore lush trails and observe local wildlife, making it a perfect outdoor adventure for families seeking nature experiences in this scenic region.
- Local Community Parks: Enjoy family picnics, playground fun, and open green spaces designed for relaxation and active play within the area’s welcoming parks.
- Educational Museums: Visit regional museums to engage children with interactive exhibits that highlight the area's history and culture, enriching your family’s educational experience.
- Recreational Water Activities: Take advantage of nearby lakes and waterways for gentle kayaking, fishing, or swimming, ideal for family bonding in the tranquil surroundings here.
Adult Activities
- Hiking and Nature Trails: Explore the scenic beauty of the region through well-maintained trails that showcase the area's lush landscapes and tranquil surroundings.
- Local Wineries and Breweries: Taste regional craft beverages at nearby wineries and breweries, offering a relaxing experience amid picturesque vineyard and brewery settings.
- Golfing:** Enjoy a round of golf at renowned courses nestled within the region, ideal for both casual players and avid enthusiasts.
- Fishing and Boating:** Discover the waterside charm by fishing in local lakes or taking a boat out to enjoy the serene aquatic environment here.
Other Places to Stay in Highland, WI
Highland Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Local Events: Research upcoming events and seasonal activities in the area to enhance your experience and make reservations early for popular attractions.
- Explore Natural Beauty: Take advantage of the region's scenic outdoor spaces, including parks and trails, to enjoy the best of Highland’s serene landscape.
- Connect with Local Amenities: Familiarize yourself with nearby shops, restaurants, and essential services to ensure a convenient and comfortable stay.
- Choose the Right Vacation Rental: Select a property that suits your needs and offers easy access to key points of interest within the destination to maximize your time here.
Transportation Options
- Highland Transit Service: This reliable local transit option offers convenient transportation for exploring the region around Highland, Wisconsin, especially when staying in vacation rentals nearby.
- Rental Car Services: Major rental companies operate here, giving you flexible travel options to explore the scenic areas and attractions at your own pace.
- Private Shuttle Services: Available for tailored trips and group transfers, providing a comfortable way to reach popular destinations within Highland and surrounding areas.
- Bike Rentals: A popular eco-friendly choice that allows you to enjoy the natural beauty of Highland at a leisurely pace right from your vacation rental.
Local Customs Options
- Traditional Irish Festivals: Celebrated with lively music and dance, these festivals reflect the area's rich Irish heritage and are a vibrant part of local cultural gatherings.
- Community Fish Boils: As a beloved local custom, community fish boils in the region bring residents and visitors together to enjoy freshly cooked fish in a rustic setting.
- Historic Building Preservation: Respect for historic architecture is a key aspect of the area's identity, with many buildings maintained and celebrated as part of Highland's unique charm.
- Farmers' Market Traditions: Supporting local agriculture, farmers' markets here showcase fresh produce and handcrafted items, embodying the region’s emphasis on sustainable living and community connection.
Frequently Asked Questions About Highland?
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
- Unique! A renovated old railroad depot turned into a cozy cottage.
- River's Edge Cabin, LLC
- 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
- Riverside Chalet, LLC
- 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.
2. Which vacation homes in Highland are best for families?
If you are looking for a family-friendly vacation home in Highland, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Highland:
3. How many Rentbyowner vacation rentals are available in Highland?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 44 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.
4. What is the cancellation policy for vacation rentals in Highland, Wisconsin?
Cancellation policies vary by property, so you should review the specific listing details or contact the owner directly to understand the terms and any applicable fees.
5. Are there any additional fees I should be aware of when booking a rental in Highland?
Additional fees such as cleaning, service charges, or local taxes are typically outlined in the listing. It's best to read the complete property description or ask the host for clarification.
6. How do I confirm my booking and what is required upon check-in?
Once you select and book a property, you'll receive confirmation details. Check-in procedures, including any requirements like ID verification or security deposits, will be specified by the host within the listing.
7. Is there a minimum stay requirement for vacation rentals here?
Minimum stay requirements differ among properties, so it's important to review the individual listing details or communicate directly with the host to confirm the length of stay needed.
8. What amenities are typically included in Highland vacation rentals?
Amenities vary per property but often include essentials such as Wi-Fi, kitchen facilities, parking, and outdoor space. For specific amenities, please refer to the listing description or contact the owner directly.
