Discover Your Perfect Highland Vacation Homes

Why Choose Rent By Owner for your Highland Vacation Rental Homes?

What makes our Vacation Rentals 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 Highland

When should you plan your Vacation Rentals stay?

To make the most of your stay, consider visiting during the shoulder seasons when this destination offers pleasant weather and fewer crowds, ensuring a more relaxed experience while exploring Highland's charming surroundings.

Peak Season Highlights

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Summer (June to August)

During the warmest months, you'll enjoy pleasant daytime temperatures ideal for outdoor activities and exploring the area's natural beauty.

Average Temperature Daytime: around 80°F - Nighttime: around 60°F
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Fall (September to November)

This season offers cooler weather and vibrant foliage, creating a picturesque backdrop for your stay in this destination.

Average Temperature Daytime: mid 70s°F - Nighttime: mid 50s°F

Off-Season Highlights

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Winter (December to February)

The colder months bring a quieter atmosphere, making it an excellent time for those seeking peaceful escapes and cozy accommodations.

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

As the region awakens from winter, you can experience mild temperatures and fewer crowds while enjoying the emerging blossoms.

Average Temperature Daytime: mid 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

More Top-Rated Vacation Rentals in Highland Area

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 outdoor grilling with a private barbecue area to enhance your stay.
  • Relax on the spacious patio or deck, perfect for soaking up the sunshine.
  • Take advantage of well-maintained walking or biking trails nearby for outdoor adventures.
  • Make use of a parking space suited for boats or RVs if you're exploring the region in larger vehicles.
  • Benefit from scenic picnic areas ideal for family gatherings or romantic outings.
  • Experience the convenience of outdoor furniture designed for lounging and socializing.
  • Utilize dedicated outdoor spaces for sports or recreational activities during your visit.

Top Attractions Around Highland

What attractions are nearby?

Here, you can explore a variety of outdoor activities and local attractions that showcase the best of the region, making your stay both enjoyable and memorable.

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Family Activities

  • Northwest Indiana Film & Television Archive Tour: Discover local cinematic history on a guided tour, perfect for family members interested in film and television production.
  • Canoeing and Kayaking at Wicker Park: Enjoy a day on the water with your family by renting canoes or kayaks at this scenic park within the region.
  • Highland History Museum Visit: Engage with the area's past through interactive exhibits and family-friendly activities that showcase the local heritage.
  • A walk through Highland Town Center: Stroll around the vibrant town center, where you can explore shops, enjoy local eateries, and participate in seasonal events suitable for all ages.
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Adult Activities

  • Explore the Indiana University Northwest Campus: Engage with the vibrant academic atmosphere and cultural events that are accessible from here, perfect for enriching your visit.
  • Visit the Highland Park: Enjoy outdoor activities, scenic walking paths, and relaxing green spaces in this local favorite spot to unwind and connect with nature.
  • Discover local dining experiences: Savor a variety of cuisines at the nearby restaurants, offering a taste of regional flavors just moments from your accommodation.
  • Experience community festivals and events: Participate in seasonal celebrations and local gatherings that showcase the region’s friendly atmosphere and cultural diversity.

Highland Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead for Local Events: Check the area's event calendar to align your stay with local festivals or seasonal activities, enhancing your experience in Highland, Indiana.
  • Explore Nearby Nature Spots: Take advantage of the region’s natural beauty by visiting parks and outdoor spaces that showcase Highland's scenic landscape.
  • Utilize Public Transportation Options: Familiarize yourself with available transit services to easily navigate the area without hassle during your visit.
  • Choose a Convenient Location: Select vacation rentals situated close to key attractions and amenities to maximize your leisure time here.

Transportation Options

  • Personal Vehicle: Traveling by car offers you the flexibility to explore Highland and the surrounding region at your own pace, with ample parking options near your vacation rental.
  • Public Transit: Local bus services provide an affordable and convenient way to navigate within Highland and connect to nearby cities in the area.
  • Taxi and Rideshare Services: Reliable taxi companies and rideshare options like Uber and Lyft ensure comfortable transportation directly from your Highland accommodation.
  • Rental Cars: Renting a car gives you the freedom to visit attractions outside Highland while enjoying the comfort and convenience of a private vehicle.

Local Customs Options

  • Local Celebrations and Parades: Participating in seasonal parades and community celebrations here offers a glimpse into the area's rich cultural traditions.
  • Respect for Community Events: Engaging with local festivals and markets reflects the region’s close-knit spirit and appreciation for shared customs.
  • Dining Etiquette: Enjoying regional cuisine involves embracing casual dining manners that emphasize friendliness and communal enjoyment.
  • Historical Reverence: Honoring the area's history by visiting local landmarks or museums allows you to connect more deeply with the community's heritage.

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:

2. How many vacation rentals have private pools in Highland?

There are 5 vacation rentals with private pools near Highland. Top-rated RBO homes that have access to a swimming pool include:

3. 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:

4. How many Rentbyowner vacation rentals are available in Highland?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 51 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. 

5. What is the cancellation policy for vacation rentals in Highland, Indiana?

Cancellation policies vary by 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.

6. How do I ensure my booking is secure when reserving a vacation rental here?

Reservations are processed through a trusted platform that offers secure payment options. For added peace of mind, confirm the listing's reviews and communicate with the property owner before finalizing your booking.

7. Are there any additional fees I should be aware of when booking a vacation rental in this area?

Additional fees such as cleaning fees, service charges, or local taxes may apply. Details about these charges are typically disclosed on the listing page, but it’s advisable to review them carefully or contact the owner for clarification.

8. What amenities can I expect at vacation rentals in Highland, Indiana?

Amenities vary between properties, so it's best to check each listing for details. Many rentals offer features like Wi-Fi, parking, and fully equipped kitchens to enhance your stay here.

9. How do I contact the property owner if I have questions before booking?

You can reach out directly through the messaging feature on the listing platform. Owners are usually responsive and happy to assist with any questions you have about the property or the booking process.