Highwood Accommodations

House

Charming Lake Forest Country Estate

10.0

Exceptional

(1 Review)

2 Bedrooms 2 Baths 2 Guests

US $331/Night 7 Nights - US $2,317

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New

Apartment

USS Russell

4 Bedrooms 2 Baths 11 Guests 2066.67 ft²

US $542/Night 7 Nights - US $3,794

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Apartment

Safe & Secure Parkview-Sleep Sanctuary+Kitchen

10.0

Exceptional

(1 Review)

1 Bedroom 1 Bath 2 Guests

US $115/Night 7 Nights - US $806

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New

Apartment

USS Alexandria

1 Bedroom 1 Bath 11 Guests 2066.67 ft²

US $537/Night 7 Nights - US $3,761

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Apartment

Cozy 2 bed Apt- 2 train stops to the Naval Base!

9.4

Exceptional

(3 Reviews)

2 Bedrooms 1 Bath 7 Guests 743 ft²

US $279/Night 7 Nights - US $1,951

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New

Apartment

Cozy 2 bed Apt 2 train stops to the Naval Base

2 Bedrooms 1 Bath 7 Guests 753.47 ft²

US $305/Night 7 Nights - US $2,133

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Apartment

Stunning & Stylish Downtown Studio - Highland Park

8.4

Excellent

(7 Reviews)

1 Bedroom 1 Bath 2 Guests

US $190/Night 7 Nights - US $1,328

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New

House

Modern 4BD 2BA Home Near Downtown Metra

1 Bedroom 2 Baths 8 Guests 129.17 ft²

US $529/Night 7 Nights - US $3,703

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Apartment

Chic Studio in Downtown Highland Park near Metra

8.0

Excellent

(4 Reviews)

1 Bedroom 1 Bath 2 Guests

US $174/Night 7 Nights - US $1,217

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Apartment

Clean, Quiet, Secure, with Beautiful Park Views - 1 bedroom plus den in Rivinia

2.0

Average

(1 Review)

1 Bedroom 1 Bath 3 Guests

US $178/Night 7 Nights - US $1,248

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Apartment

Charming 2-bedroom apartment in delightful Highwood 2 minutes to Train station!

2 Bedrooms 1 Bath 7 Guests 700 ft²

US $173/Night 7 Nights - US $1,208

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Near Ravinia and Navy Base, charming 3-bedroom house in peaceful Highland Park

Price Dropped

House

Near Ravinia and Navy Base, charming 3-bedroom house in peaceful Highland Park

10.0

Exceptional

(6 Reviews)

3 Bedrooms 4 Baths 7 Guests

US $544/Night 7 Nights - US $3,806

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More Top-Rated Accommodations in Highwood Area

Why Choose Rent By Owner for your Highwood Accommodations?

What makes our Accommodations special?

Verified Listings

Book with confidence knowing every property meets our quality and safety standards.

Unbeatable Value

Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.

Diverse Options

From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Highwood

When should you plan your Accommodations stay?

Timing your visit to this destination wisely can enhance your experience, so consider the seasonal trends and local climate to choose the best period for booking accommodations here and fully enjoy what the region has to offer.

Peak Season Highlights

Summer (June to August)

During the summer months, the area experiences warm weather ideal for outdoor activities and exploring local sites.

Average Temperature Daytime: around 80°F (27°C) - Nighttime: 60°F (15°C)

Fall (September to November)

Early fall offers pleasant temperatures and vibrant foliage, making it a popular time to visit this destination before winter sets in.

Average Temperature Daytime: mid 70s°F (24°C) - Nighttime: around 50°F (10°C)

Off-Season Highlights

Winter (December to February)

The winter season sees cooler temperatures and fewer visitors, providing a quieter experience while still offering seasonal charm.

Average Temperature Daytime: mid 30s°F (1-2°C) - Nighttime: around 20°F (-6°C)

Spring (March to May)

In early spring, the region begins to thaw with milder weather, attracting those seeking a less crowded travel period.

Average Temperature Daytime: mid 50s°F (12-14°C) - Nighttime: around 35°F (2°C)

Weekly Weather Forecast for Highwood

How to Book Your Highwood Accommodations

What's our booking process?

Our platform allows you to browse a curated selection of accommodations. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

Search Properties

Use our filters to find the right property that fits your needs.

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Highwood

More Top-Rated Accommodations in Highwood Area

Common Accommodations Amenities

What amenities can you expect?

Our Accommodations are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

Fully-equipped kitchens with modern appliances
Comfortable living areas with flat-screen TVs
Free Wi-Fi for staying connected
Air conditioning and heating for year-round comfort
In-unit washers and dryers for convenience
Luxurious bedrooms with premium bedding
Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

Enjoy a private outdoor patio or deck to unwind after exploring the area
Take advantage of landscaped gardens or yard space for relaxing or outdoor dining
Access a shared or private outdoor pool to cool off during warmer months
Make use of outdoor grilling facilities for enjoyable cookouts with family and friends
Benefit from convenient parking areas that accommodate outdoor storage or vehicles
Experience scenic views from balconies or verandas overlooking the surrounding region
Utilize common outdoor spaces such as picnic areas or lawns for leisure activities

Top Attractions Around Highwood

What attractions are nearby?

When visiting Highwood, Illinois, you can enjoy a variety of nearby activities such as exploring local parks, experiencing vibrant cultural festivals, or indulging in diverse dining options-all within easy reach of your planned stay in this welcoming area.

Family Activities

Highwood’s Downtown District Explore this charming area with family-friendly shops, cafes, and vibrant street festivals that showcase the local culture.
Northern Illinois University Campus Visit the scenic campus for outdoor activities, cultural events, and educational experiences suitable for all ages.
Harms Woods Forest Preserve Enjoy outdoor adventures like hiking, picnicking, and nature walks in this peaceful natural setting nearby.
Ragdale Participate in family art programs and workshops held at this renowned arts community, fostering creativity for children and adults alike.

Adult Activities

Visit the Highwood Cultural Center Engage with local art exhibitions and cultural events that showcase the vibrant heritage of this region.
Explore the Lake County Forest Preserve District Enjoy scenic walking, biking trails, and opportunities to connect with nature in a peaceful setting.
Relax at local breweries and pubs: Experience the area's craft beverage scene through visits to popular breweries that offer tastings and tours.
Attend live music and entertainment events Discover concerts and performances held at various venues around here, providing lively entertainment options for adults.

Highwood Travel Tips

How Can You Make the Most of Your Stay?

Explore local dining options: Take advantage of the area’s vibrant food scene to enjoy authentic flavors and support neighborhood eateries during your stay.
Visit nearby outdoor spaces: Embrace the region's scenic parks and outdoor areas for relaxing walks or outdoor activities that showcase the natural beauty here.
Utilize transportation services: Plan your trips around town using local transit or rental car services to easily access key attractions in this destination.
Book well in advance: To secure the best property types and locations, especially in peak seasons, be sure to reserve your accommodations early through a trusted platform.

Transportation Options

Metra Commuter Rail This regional train service provides convenient transportation options connecting Highwood with downtown Chicago and other suburbs, making it easy to explore the region.
Local Bus Services Accessible bus routes within and around the area offer an affordable way to navigate Highwood and reach nearby attractions or transportation hubs.
Taxi and Rideshare Services Taxis and rideshare companies like Uber and Lyft operate in this destination, offering flexible door-to-door transportation for your comfort and convenience.
Car Rentals Renting a vehicle here grants you the freedom to explore the region on your own schedule, especially convenient if you're planning to visit attractions outside the immediate area.

Local Customs Options

Local Art Celebrations Participating in community art festivals showcases the region’s vibrant creative spirit and appreciation for local talent.
Traditional Dining Etiquette Respect for local dining customs, such as specific table manners, enhances your experience when enjoying regional cuisine here.
Community Events and Gatherings Engaging in neighborhood events fosters a deeper connection with the area’s friendly and welcoming residents.
Historical Preservation Practices Observing and respecting local historical sites and traditions helps preserve the unique heritage of this destination.

Frequently Asked Questions about Highwood Accommodations

1. What are the top Accommodations in Highwood?

There are a lot of options in Highwood. If you plan on staying in the Highwood area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Accommodations in Highwood:

2. How many Accommodations are available in Highwood?

Currently, the total number of properties listed by RBO in 2026 is over 36 in the Highwood area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Accommodations in Highwood. 

3. What is the cancellation policy for bookings in this area?

Cancellation policies vary depending on the specific property and owner. To understand the options available, please review the property's details or contact the host directly before completing your reservation.

4. How do I find the best accommodations near popular attractions here?

To locate top-rated stays close to prominent attractions, use the search filters on the site to sort by reviews, amenities, and location. You can also read guest reviews to ensure the property meets your expectations.

5. Are there any additional fees I should be aware of when booking?

Additional fees such as cleaning or service charges may apply depending on the property. These details are typically outlined in the listing description, so review the information carefully before booking.

6. What amenities are commonly offered in accommodations here?

Many properties include amenities like Wi-Fi, parking, kitchen facilities, and air conditioning. Specific offerings vary by listing, so check each property's details to find accommodations that suit your needs.

7. How can I ensure my booking is secure and reliable?

Bookings made through verified listings on this platform are protected. For added security, always communicate through the official messaging system and confirm all reservation details with the host prior to arrival.