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Highwood vacation rentals

We found 175 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Scroll through and select from vacation rentals in Highwood to find one that's perfect for your trip. Whether you’re staying in a vacation home with friends, family, or even just your pets, you'll have the best amenities for spending time at your home away from home, which might include a hot tub and a washer and dryer. Whatever you're looking for, you'll find a rental for everyone's needs, including accessible or non-smoking choices.

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Choose a vacation rental for your Highwood getaway

Experience the unique character of Highwood with a stay in a vacation home rental. This city is well-known for its shopping and restaurants. Naval Base Great Lakes and Six Flags Great America are just a couple of the must-sees in the area. Whether you're planning a family vacation, friends trip or romantic retreat, Vrbo has a great selection of vacation 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 things to do while you're in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Highwood a one-of-a-kind vacation spot. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • Six Flags Great America (12.7 mi / 20.4 km)
  • Sportsman's Country Club (5.5 mi / 8.8 km)
  • Northbrook Sports Complex (6.2 mi / 9.9 km)
  • Home Alone House (7.9 mi / 12.7 km)
  • The Glen Club (8.1 mi / 13 km)
  • Kemper Lakes Golf Club (9.6 mi / 15.5 km)

Exploring the natural landscape of Highwood

Whether you're an active traveler or just want to take in the scenery, Highwood is a great spot to appreciate mother nature. Here are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city center:

  • Ravinia Park (3.9 mi / 6.2 km)
  • Chicago Botanic Garden (4.3 mi / 7 km)
  • Heritage Park (7.4 mi / 11.9 km)
  • Waukegan SportsPark (15.2 mi / 24.4 km)
  • Illinois Beach State Park (15.4 mi / 24.8 km)
  • North Shore Beach Park (16.2 mi / 26 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 center. If you're unable to find a flight that fits your schedule, you might consider flying into Chicago O'Hare Intl. Airport (ORD), which is 16.6 mi (26.6 km) away.

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

Frequently asked questions

How much does it cost to rent a vacation rental in Highwood?

The average price for a vacation rental in Highwood is based on a number of factors, including property type, length of stay and season. Whether you're dreaming about a sprawling villa with lots of bedrooms or a quaint cabin for just you and the kids, just enter your dates of travel to view stays with amazing value.

How much does it cost to rent a beach house in Highwood?

The average price for a vacation rental by the beach in Highwood depends on when you're going and the size and style of property you're searching for. You can easily find prices on Vrbo by entering your destination and travel dates. Then use the filters to choose the number of bedrooms and amenities essential to you, like WiFi, air conditioning and a hot tub.

What are the top attractions for families in Highwood?

Keeping the kids happy during your Highwood vacation is a breeze with these fabulous family-friendly attractions:

  • Kohl Childrens Museum
  • Wagner Farm
  • Grove National Historic Landmark

How old do you have to be to rent a vacation rental in Highwood?

It's a good idea to check with the Highwood vacation property you'd like on Vrbo as age restrictions differ. However, it's normally 16, 18 or 21.

How long can I rent a vacation rental in Highwood for?

It's up to the Highwood property. To see all available options offering extended stays, just type your dates and number of people into Vrbo. You can look forward to having the entire place to yourself, as well as comforts such as a full kitchen, air conditioning and a yard where the kids can run and play. Keep an eye out for any long-term stays that offer discounted weekly or monthly prices.

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