Photo by Joe Farmer

Highland holiday lettings

We found 172 holiday rentals — enter your dates for availability

Discover a selection of holiday rentals in Highland that are perfect for your trip. Holiday homes offer the best amenities for you and your friends, family or even pets, such as parking and a TV. At the end of the day, you'll be sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

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The charming city of Highland awaits you

Enjoy the churches and other features of Highland. Travellers to this romantic city praise the ice skating, basketball games and bird watching. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in Highland

Are you hoping to find attractions to see while you're in the area? Venture out of your holiday home and experience everything that makes Highland a one-of-a-kind holiday spot. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Ravisloe Country Club (11.3 mi / 18.1 km)
  • Deep River Water Park (13 mi / 21 km)
  • Turkey Creek Golf Course (6.5 mi / 10.4 km)
  • Coyote Run Golf Course (12.5 mi / 20.2 km)
  • Chicago State University (14 mi / 22.5 km)
  • Lost Marsh Golf Course (7.9 mi / 12.7 km)

Exploring the natural landscape of Highland

Whether you're looking for exciting outdoor activities or just want to take in the scenery, you'll be sure to find the perfect setting for your holiday in Highland. Here are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Indiana Dunes National Park (21.2 mi / 34.1 km)
  • Centennial Park (3.1 mi / 5 km)
  • Hammond Sportsplex & Community Center (3.1 mi / 5.1 km)
  • Crown Point Sports Complex (10.9 mi / 17.5 km)
  • Marquette Park (11 mi / 17.7 km)
  • Marquette Beach (11.1 mi / 17.9 km)

Transport to and around Highland

The nearest airport is in Chicago Midway Airport (MDW), located 22 mi (35.5 km) from the city centre. If you're unable to find a flight that fits your schedule, you can also fly into Chicago O'Hare International Airport (ORD), which is 37.4 mi (60.2 km) away.

Frequently asked questions

What is the best area to stay in Highland when booking a holiday rental?
When considering a holiday rental in Highland, Indiana, the neighbourhood around the historic downtown area is an excellent choice. This vibrant part of the town offers a blend of charming local shops, delightful eateries, and easy access to community events, making it a lively hub for visitors. Notably, the nearby Main Square Park is a lovely spot for relaxation and outdoor activities, featuring walking trails and picnic areas that families and solo travellers alike can enjoy.

Another appealing area is close to the Highland Grove Shopping Centre, which provides a variety of retail options and dining experiences. This area is particularly convenient for those who appreciate having amenities within easy reach. With a range of properties available, from cosy apartments to spacious homes, you'll find options that cater to different group sizes and preferences.
How much does it cost to rent a holiday home in Highland?
Prices for holiday rentals in Highland vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Highland to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Highland holiday house rentals?
You can find great discounts on house rentals in Highland on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of holiday rental accomodation in Highland?
In Highland, holiday houses are the predominant type of holiday rental, with around 12 available throughout the area. These homes typically offer a spacious environment with multiple bedrooms, fully equipped kitchens, and comfortable living areas—ideal for families or groups. Many of these properties also feature outdoor spaces such as gardens or patios, providing a lovely setting for relaxation after exploring local attractions.
Can I find long-stay holiday rentals in Highland?
A long-stay holiday rental in Highland is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Highland?
In Highland, Indiana, there are several pet-friendly house rentals available for those looking to enjoy a comfortable stay with their furry companions. Many of these properties offer amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, making them suitable for families or groups.

The neighbourhood itself is well-situated, providing easy access to local parks and green spaces where pets can enjoy some outdoor time. Nearby, the Lake County Fairgrounds offers a variety of events and activities, while the scenic Wolf Lake provides opportunities for walking and enjoying nature.
Are there any remote work holiday rentals in Highland?
In Highland, Indiana, there are several remote work holiday rentals available, making it a suitable destination for those looking to balance work and leisure. Many properties in the area come equipped with reliable internet provided by third-party services, ensuring that guests can stay connected while working remotely.

The town is conveniently located near various amenities, including parks and local shops, providing opportunities for breaks and relaxation after a day's work. Additionally, the surrounding region offers recreational activities and outdoor spaces, superb for a bit of downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Highland holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Highland with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Highland?
In Highland, popular rental amenities include onsite parking, air conditioning, and kitchens equipped for self-catering. Many properties also feature coffee and tea makers, ensuring guests can enjoy their favourite hot beverages at any time. Additionally, some rentals are pet-friendly, allowing travellers to bring their furry companions along for the stay.
When is the best time to visit Highland for a holiday rental?
July is the most popular month to visit Highland, Indiana, offering a vibrant setting for holidaymakers. This peak season, which spans from May to July, draws many visitors eager to enjoy the warm weather and local festivities. During these months, outdoor activities abound, with families and friends flocking to parks for picnics, enjoying the lively local events, and making the most of the beautiful summer days.

In July, temperatures typically range from the mid-teens to low 30s Celsius, providing ideal conditions for sightseeing and outdoor adventures. You can explore the scenic trails in nearby parks or take part in community events that showcase local culture and cuisine. The sense of community and excitement makes this time particularly special for those looking to engage with Highland's charm.

For those keeping an eye on their budgets, October presents a wonderful opportunity to visit Highland at a more affordable rate. With fewer crowds, you can appreciate the area's autumn beauty at a leisurely pace, enjoying the stunning fall foliage and the crisp air. This period is great for scenic walks and discovering hidden gems without the hustle and bustle of peak season.

Ultimately, your choice of when to visit Highland will depend on whether you thrive in the lively summer atmosphere or prefer the tranquillity and beauty of the fall.
How early should I book a Highland holiday rental?
Book your Highland holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Highland?
In Highland, Indiana, visitors can enjoy several attractions that highlight the area's charm. The local parks, such as the picturesque Main Square Park, offer lovely walking paths, playgrounds, and sports facilities, making it a great spot for families and outdoor enthusiasts. Nearby, the South Shore Line provides easy access to Chicago, allowing for day trips to explore the city's numerous attractions while returning to the peaceful surroundings of Highland.

For those interested in history, the Highland Historical Society showcases the town's heritage and features informative exhibits. The area also hosts various community events throughout the year, fostering a lively option.
Can I change or cancel my Highland home rental booking on Vrbo?
To find Highland holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Highland holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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