Photo by Tara Jabbari

Highwood holiday rentals

We found 229 holiday rentals — enter your dates for availability
Discover a selection of 8 apartments and other holiday rentals in Highwood that are perfect for your trip. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll have the amenities that you expect and more, which might include Wi-Fi and a hot tub. Whatever you're looking for, you're sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

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Choose a holiday rental for your Highwood getaway

Learn about the unique charm of Highwood with a stay in a holiday home rental. This city is well-known for its shopping and restaurants. Six Flags Great America and Donald E. Stephens Convention Center are just a couple of the must-see attractions in the area. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in Highwood

Do you want to discover attractions to see while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Highwood a fun place to get away to. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Six Flags Great America (12.7 mi / 20.4 km)
  • Northbrook Sports Complex (6.2 mi / 9.9 km)
  • Chevy Chase Country Club (6.4 mi / 10.2 km)
  • The Glen Club (8.1 mi / 13 km)
  • Kemper Lakes Golf Club (9.6 mi / 15.5 km)
  • Great Wolf Lodge Water Park (13.9 mi / 22.3 km)

Exploring the natural landscape of Highwood

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

  • Chicago Botanic Garden (4.3 mi / 7 km)
  • Heritage Park (7.4 mi / 11.9 km)
  • Isaak Walton Park (9.7 mi / 15.7 km)
  • Waukegan Harbor (10.8 mi / 17.3 km)
  • Dawes Park (13.3 mi / 21.4 km)
  • Deer Grove Forest Preserve (13.5 mi / 21.7 km)

How to get to and around Highwood

The nearest airport is in Chicago, IL (PWK-Chicago Executive), located 7.6 mi (12.3 km) from the city centre. If you can't find a flight that's convenient for your trip, you can also fly into Chicago O'Hare International Airport (ORD), which is 16.6 mi (26.6 km) away.

If you prefer train travel, make your way to Highwood Station or Highland Park Fort Sheridan Station and explore the city from there.

Frequently asked questions

What is the best area to stay in Highwood when booking a holiday rental?
When considering a holiday rental in Highwood, Illinois, the best area to stay in is near the vibrant downtown. This charming neighbourhood offers a delightful mix of local shops, cafes, and restaurants, great for immersing yourself in the community's special environment. One of the highlights of staying in this area is its proximity to the beautiful Lake Michigan shoreline, where you can enjoy scenic views and leisurely walks along the waterfront.Just a short distance away, you'll find the renowned Ravinia Park, which is famous for its outdoor music festival and lush gardens, making it a great spot for a picnic or an evening concert. The downtown area is home to a variety of properties, ranging from quaint apartments to family-sized homes, providing ample options for different group sizes and preferences.
What is the most popular type of holiday rental accomodation in Highwood?
In Highwood, apartments are the most common type of holiday rental, with about 12 available throughout the area. These apartments are typically situated in convenient locations, offering easy access to local amenities and attractions. Most units come with fully equipped kitchens, comfortable living areas, and some may even feature private balconies for enjoying the surroundings.Additionally, there are several charming cottages that provide a more unique and homely experience. These cottages often include multiple bedrooms, outdoor spaces, and a rustic atmosphere, making them ideal for families or groups looking for a relaxing getaway.
Are there any family house rentals in Highwood?
In Highwood, Illinois, there are several family-friendly house rentals available, making it an excellent choice for those travelling with children. The neighbourhood offers spacious homes with modern amenities, including fully equipped kitchens for preparing family meals, large living areas for relaxing together, and outdoor spaces for play. Many properties also feature conveniences like Wi-Fi and air conditioning, ensuring a comfortable stay.Visitors will appreciate the proximity to local parks, where children can enjoy playgrounds and sports facilities. Additionally, the vibrant dining scene in nearby Highland Park provides a variety of family-friendly restaurants.
Are there pet-friendly house rentals in Highwood?
In Highwood, there are several pet-friendly house rentals available, offering a great opportunity for travellers who wish to bring their furry companions along. Many of these homes come equipped with amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups.The neighbourhood is conveniently located near several parks, including Everts Park and the popular Highwood Recreation Centre, where pets are welcome, providing ample space for walks and play. Additionally, the area features pet-friendly cafes and shops, ideal for those travelling with pets.
Are there any remote work holiday rentals in Highwood?
In Highwood, there are several remote work holiday rentals available, with around 12 options to choose from. This charming suburb offers a peaceful environment, making it ideal for those looking to balance work and relaxation. Many properties come equipped with essential amenities for remote work, including free Wi-Fi, dedicated workspaces with desks and chairs, and sometimes even additional features like computer monitors to enhance productivity.The area is conveniently located near local parks and the scenic Lake Michigan waterfront, providing opportunities for leisurely breaks during the workday. Additionally, Highwood's vibrant dining scene and community events add to the appeal, ensuring guests have plenty of options for unwinding after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Highwood?
In Highwood, popular rental amenities cater to a variety of needs, making stays comfortable and enjoyable. Many properties permit pets, ensuring that travellers can bring their furry companions along. Additionally, service animals are welcomed, providing peace of mind for those requiring assistance.Rentals often feature coffee and tea makers, allowing guests to enjoy a warm beverage at any time. For those needing to catch up on work or stay connected, many accommodations provide desks. Families will appreciate that many properties include games specifically designed for children, adding an element of fun for younger guests.
When is the best time to visit Highwood for a holiday rental?
The best time to book a holiday rental in Highwood is during the peak season from July to September, when the area comes alive with vibrant events and outdoor activities. July stands out as the most popular month, welcoming families and travellers eager to enjoy warm summer weather, with temperatures often reaching the mid to high 20s Celsius. This is an ideal time for alfresco dining at local restaurants, exploring the beautiful parks, and participating in community festivals that showcase the rich culture of the region.The summer months provide ample opportunities for outdoor adventures, including leisurely strolls along the scenic Lake Michigan shoreline and visits to nearby attractions. The pleasant climate and lively option make it great for sightseeing and enjoying the local charm.For those looking for a more budget-friendly experience, consider visiting in February. While this month is part of the low season, it offers unique winter activities such as ice skating and cosy gatherings at local cafés. Plus, you'll enjoy a quieter environment, allowing for a more relaxed holiday experience.Ultimately, your choice will depend on whether you prefer the bustling energy of summer or the peaceful charm of winter in Highwood.
What are the top attractions in Highwood?
In Highwood, visitors can enjoy a range of attractions that showcase the area's charm and community spirit. One of the highlights is the picturesque downtown area, where you can find a variety of local shops and restaurants, superb for a leisurely stroll. The city's proximity to the beautiful Lake Michigan offers opportunities for outdoor activities, including boating and picnicking along the shoreline.The Highwood Public Library is another great spot, often hosting community events and activities, making it a hub for local culture. Additionally, the nearby Ravinia Festival is a must-visit, especially for music lovers, as it features a summer-long series of concerts in a scenic outdoor setting.For those interested in nature, the nearby Lake County Forest Preserves provide ample opportunities for hiking, birdwatching, and enjoying the natural beauty of the area.
Are all fees included in the Highwood holiday homes prices shown on Stayz?
Stayz 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.
Are there any Highwood holiday homes with parking?
Stayz offers a wide selection of holiday homes in Highwood 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 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.
Are there any discounts for Highwood holiday homes?
You can find great discounts on holiday homes in Highwood on Stayz, 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.
Can I change or cancel my Highwood holiday home booking on Stayz?
To find Highwood holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Highwood?
A long-stay holiday home in Highwood 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Highwood holiday home?
Book your Highwood holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Highwood?
Prices for holiday homes in Highwood 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Highwood to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.