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Highwood vacation rentals

We found 201 vacation rentals — enter your dates for availability

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.

Vacation rentals with weekly discounts - Highwood

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Find out more about Highwood

Find out more about Highwood

Why visit Highwood

  1. Family-Friendly Activities: Highwood is perfect for families, offering fun outings at the Highwood Recreation Center and local parks.
  2. Scenic Beauty: Enjoy picturesque views and natural surroundings, ideal for picnics and outdoor adventures.
  3. Art-Filled Streets: Explore charming neighbourhoods adorned with local art, fostering a vibrant atmosphere.
  4. Proximity to Highland Park: A short trip to Highland Park provides additional attractions and activities.
  5. Diverse Accommodations: Choose from a variety of vacation rentals, including cozy apartments and spacious homes.

Popular types of accommodation in Highwood

When exploring Highwood, you'll find a variety of vacation rentals to suit your needs. From cozy apartments and spacious houses to modern condos, there's something for everyone. Whether you're searching for a highwood rental, a charming apartment in Highwood, or a vacation house rental, we provide the transparency and reassurance you need to make the best choice for your getaway. Enjoy your stay in beautiful Highwood!

  • Apartments: The most sought-after option in Highwood, offering convenient access to amenities and local attractions for solo travellers or couples.
  • Houses: A popular choice for families or groups, providing spacious and comfortable living spaces for a home-like experience.
  • Condos: Ideal for those seeking a mix of comfort and luxury, often featuring modern amenities in prime locations.
  • Cottages: Perfect for a cozy getaway, these charming rentals provide a quaint atmosphere often surrounded by nature.
  • Cabins: A great option for those looking to immerse themselves in the outdoors, offering rustic charm in a serene setting.**

Top attractions in Highwood

Highwood, Illinois, is ideal for family vacations, offering a blend of outdoor activities and scenic experiences. Visitors can explore local attractions like modern universities, beautiful beaches, and event venues. Notable activities include discovering Highwood itself and enjoying the Highwood Recreation Center, making it perfect for those seeking city life combined with family-friendly fun and outdoor adventures.

  1. Six Flags Great America: This exciting theme park offers thrilling rides, live entertainment, and fun for the entire family, making it a perfect spot for adventure seekers and those looking to enjoy a day filled with laughter.
  2. Northwestern University: A prestigious modern university with stunning architecture and vibrant city vibes, ideal for a leisurely stroll and appreciating the blend of education and urban life.
  3. Chicago Botanic Garden: A serene botanical garden featuring beautiful landscapes, perfect for family outings, outdoor activities, or a romantic escape amidst nature's beauty.

Things to do recommended for couples

For a romantic getaway in Highwood, enjoy a concert at the lively Ravinia Pavilion, unwind at the luxurious Chevy Chase Country Club, or indulge in a unique dining experience at Schaumburg Medieval Times, where city romance meets medieval charm.

Things to do recommended for families

Your family will love the Northbrook Sports Complex for its wellness vibes, and Heritage Park offers a relaxing outdoor experience. For a splash of adventure, head to the Great Wolf Lodge Water Park, where fun and entertainment await just a short drive from Highwood.

Things to do recommended for groups

Experience the thrill of shopping at Gurnee Mills, just 22.5km from Highwood. Enjoy a round of golf at the scenic Highland Park Country Club, located 3.2km away, or catch a captivating show at the Marriott Theatre, a mere 9.7km from your base.

What do I need to keep in mind when booking a vacation in Highwood

If you're planning a trip with a group, family, or pets, or if you're considering an extended stay, be sure to refine your search according to your key priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Highwood with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Highwood with young kids: Traveling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, considering your closeness to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Highwood: For many families, a trip isn’t truly complete without their furry companions. If this resonates with you, explore Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Highwood: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding amenities like parking, a well-equipped kitchen, or a private pool to your search!

Where to stay in Highwood

Highwood, Illinois, offers a delightful blend of outdoor activities, scenic beauty, and family-friendly experiences. Explore the charming neighborhoods and vibrant atmosphere, where friendly locals and art-filled streets await. Just a stone's throw away, Highland Park provides additional attractions, perfect for a day trip. Whether you're enjoying a lovely picnic or indulging in local cuisine, Highwood promises an unforgettable vacation filled with warmth and community spirit.

  • Highland Park: Highland Park is a vibrant city located 3.2km from Highwood, easily accessible for a delightful day trip. Known for its family-friendly atmosphere, this city offers a plethora of outdoor activities and urban experiences. Visitors can enjoy concerts and theatre performances, while the local education institutions provide enriching opportunities. Highlights include the scenic urban parks, serene lakefront, and beautiful beaches that offer spaces for relaxation and recreation. Whether you’re looking to explore nature or enjoy cultural events, Highland Park has something for everyone.
  • Deerfield: Situated 4.8km away from Highwood, Deerfield is a charming city that attracts families and outdoor enthusiasts alike. With a range of activities available, including shopping and educational events, there is always something happening in this bustling community. The local stadium and sports facilities are popular among sports fans, while the urban parks offer a peaceful retreat for nature lovers. Deerfield’s blend of shopping and entertainment makes it an ideal destination for a well-rounded travel experience.
  • Bannockburn: Bannockburn, located 4.8km from Highwood, is a picturesque neighbourhood that caters to families seeking outdoor fun and cultural experiences. With a variety of shopping areas and theatres, visitors can enjoy an array of leisure activities. Golf enthusiasts will appreciate the nearby golf courses, while the local tourist precinct and sports facilities make it an appealing spot for all. Bannockburn’s quaint charm and community spirit provide a welcoming atmosphere for visitors looking to explore the area.

Best time to go to Highwood

If you're planning a trip to Highwood, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April, July and September, while off-peak times, like December to February tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January24.6°F (-4.1°C)Light RainMostly CloudySlightly LowSlightly Low
February25.9°F (-3.4°C)Light RainMostly CloudySlightly LowSlightly Low
March36.1°F (2.3°C)Light RainMostly CloudyAverageSlightly Low
April44.8°F (7.1°C)Light RainMostly SunnySlightly HighAverage
May55.6°F (13.1°C)Light RainMostly SunnyAverageAverage
June66.0°F (18.9°C)Light RainMostly SunnyAverageSlightly High
July72.7°F (22.6°C)Light RainMostly SunnySlightly HighSlightly High
August72.3°F (22.4°C)Light RainMostly SunnyAverageSlightly High
September66.2°F (19.0°C)Light RainMostly SunnySlightly HighAverage
October54.0°F (12.2°C)Light RainMostly SunnyAverageAverage
November41.4°F (5.2°C)Light RainMostly SunnyAverageAverage
December32.0°F (0.0°C)Light RainMostly CloudySlightly LowAverage

Booking with Vrbo is simple

Are you hoping to save on your upcoming journey? Being flexible with your travel dates can be beneficial, as prices tend to vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you find the best options for your travels!

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new adventures, pick up right where you left off, or manage and arrange your travel plans. You can easily access properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

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)
  • Conway Farms Golf Club (4.4 mi / 7.1 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)
  • Great Wolf Lodge Water Park (13.9 mi / 22.3 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:

  • 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)
  • Loyola Beach (16 mi / 25.7 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

What is the best area to stay in Highwood when booking a vacation rental?
When considering a vacation rental in Highwood, Illinois, the most appealing area to stay is the downtown district. This vibrant neighbourhood boasts a delightful mix of shops, restaurants, and entertainment options, making it a lively base for your vacation. One of the top attractions in the area is the Highwood Theatre, which offers a fantastic selection of live performances and events throughout the year, providing a taste of local culture and creativity.
How much does it cost to rent a vacation home in Highwood?
Prices for vacation rentals 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. Vrbo offers something for every taste and budget, from affordable rentals in Highwood to more spacious homes.
Are there any discounts for Highwood vacation house rentals?
You can find great discounts on house rentals in Highwood 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 vacation rental accomodation in Highwood?
In Highwood, apartments are the most popular type of vacation rental accommodation, with several available throughout the area. These rentals typically offer modern amenities such as fully equipped kitchens, comfortable living spaces, and often include access to shared facilities like pools or fitness centres. Many apartments are situated in neighbourhoods close to local attractions, restaurants, and parks, providing guests with both convenience and a taste of the local culture.
Can I find long-stay vacation rentals in Highwood?
A long-stay vacation rental 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 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 Highwood?
In Highwood, there are several pet-friendly house rentals available, making it an excellent choice for travellers looking to bring their furry companions along. Many of these properties feature comfortable amenities such as spacious living areas, fully equipped kitchens, and private outdoor spaces where pets can roam freely.
Are there any remote work vacation rentals in Highwood?
In Highwood, Illinois, there are several remote work-friendly vacation rentals available, making it an excellent choice for those looking to combine work and leisure. Many of these properties come equipped with essential amenities for remote work, such as dedicated desk spaces, comfortable desk chairs, and reliable Wi-Fi, ensuring that you can stay productive during your stay. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Highwood vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals 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 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 Highwood?
In Highwood, popular rental amenities include pet-friendly options, making it an excellent choice for travellers accompanied by their furry companions. Many properties permit pets and often feature themes that cater specifically to those with animals. Additionally, for guests with service animals, fees are typically waived, ensuring a welcoming environment for all. Highwood rentals also commonly offer free Wi-Fi in the rooms, allowing visitors to stay connected during their stay.
When is the best time to visit Highwood for a vacation rental?
July is the most popular time to visit Highwood, Illinois, as it marks the peak of the summer season, running from July to September. During this vibrant period, visitors can enjoy a wealth of outdoor activities, from exploring local parks to dining at delightful al fresco restaurants. The warm temperatures, typically in the high 20s to low 30s Celsius, create an ideal environment for leisurely strolls and community events.

July, in particular, offers a lively atmosphere with numerous festivities, including music festivals and farmers' markets, providing a genuine taste of the local culture. If you're a traveller who enjoys the buzz of summer activities and mingling with fellow visitors, this month will be particularly enjoyable.

For those who prefer a quieter experience or are looking for more budget-friendly options, February presents a wonderful alternative. While it's the low season, the charm of Highwood remains intact, and you can enjoy a more relaxed pace, with opportunities to explore indoor attractions or cosy cafés without the hustle and bustle of peak tourist traffic.
How early should I book a Highwood vacation rental?
Book your Highwood vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Highwood?
In Highwood, visitors can enjoy a variety of attractions that reflect the area's charm and community spirit. The city is known for its vibrant dining scene, especially along Waukegan Avenue, where a selection of restaurants offers diverse cuisines. Nearby, the picturesque Lake Michigan shoreline provides opportunities for outdoor activities, including walking and biking along the scenic paths.
Can I change or cancel my Highwood home rental booking on Vrbo?
To find Highwood vacation 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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Highwood vacation 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.

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