Highwood, Chicago holiday accommodation: short-term house rentals & properties

Scroll through and select from holiday rentals in Highwood to find one that's 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.

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Highwood

Re-imagined 1880's cottage walking distance to Highwood, Metra, Lake Michigan

Sleeps 6 · 2 bedrooms · 1 bathroom

Welcome to our Storybook Cottage 🏡, gushing w/ cozy-warm-spacious glitz+comfort💞

Beautiful+Serene+Upscale EcoGem by ALL the Action~>Beach+Lake+Ravinia+Train+Town

Sleeps 8 · 3 bedrooms · 1 bathroom

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, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

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. Naval Base Great Lakes and Six Flags Great America 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)
Adagio Teas (10.5 mi / 16.9 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)
Lake Park (14.1 mi / 22.6 km)
Waukegan SportsPark (15.2 mi / 24.4 km)
North Shore Beach Park (16.2 mi / 26 km)
Forest Park Beach (3.2 mi / 5.2 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

How much does it cost to rent a holiday home in Highwood?

The average price for a holiday home 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 holiday home 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 Stayz 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 holiday 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 holiday home in Highwood?

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

How long can I rent a holiday home 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 Stayz. 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.