Photo by Stephanie Garling

Highland Park holiday lettings

We found 88 holiday rentals — enter your dates for availability

Discover a selection of 5 homes and other holiday rentals in Highland Park that are perfect for your trip. Holiday rentals provide the best amenities for you and your friends, family or even pets, such as Wi-Fi and a hot tub. You'll be able to choose a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

How much does it cost to rent a holiday home in Highland Park?
Prices for holiday rentals in Highland Park 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 Park 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 Park holiday house rentals?
You can find great discounts on house rentals in Highland Park 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.
Are there any Highland Park holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Highland Park 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.
Can I find long-stay holiday rentals in Highland Park?
A long-stay holiday rental in Highland Park 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.
When is the best time to visit Highland Park for a holiday rental?
August marks the peak season for visitors to Highland Park, when the vibrant summer atmosphere draws in families and outdoor enthusiasts alike. This time of year is superb for those looking to enjoy the park's lush landscapes and partake in various recreational activities, from leisurely strolls to picnics in the sun.

As the summer sun shines, temperatures typically range from the mid-teens to low 30s Celsius, providing ideal conditions for outdoor adventures and sightseeing. The park is bustling with life, and you can easily find events and activities that cater to different interests, ensuring a memorable holiday experience.

If you're considering a more budget-friendly visit, January offers a quieter alternative. While the temperatures can dip to around 0 to 5 Celsius, this month provides a unique charm, allowing for peaceful walks and a more intimate connection with nature without the crowds.

Ultimately, the best time to book a holiday rental in Highland Park depends on your preferences.
How early should I book a Highland Park holiday rental?
Book your Highland Park 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 Park, New York, United States of America?
In Highland Park, visitors can enjoy a range of attractions that highlight the area's natural beauty and community spirit. The Highland Park itself is a focal point, featuring expansive green spaces, walking trails, and recreational facilities, making it an ideal spot for picnics and outdoor activities. Close by, the historic sites such as the Highland Park Historic District offer charming architecture and a glimpse into the area's past.

For those interested in art and culture, the nearby galleries and community events throughout the year showcase local talent and foster a sense of community. Additionally, the proximity to the shores of Lake Michigan provides opportunities for scenic views and water-related activities, enhancing the overall experience of Highland Park.
Can I change or cancel my Highland Park home rental booking on Vrbo?
To find Highland Park 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 Park 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.