Highwood, IL Cottage Rentals

Highwood Cottage Rentals

Cottage

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

10.0

Exceptional

(28 Reviews)

2 Bedrooms 1 Bath 6 Guests

US $331/Night 7 Nights - US $2,318

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The Pleasant Hill Cottage-Storybook Luxury Near Lake Michigan & Heart Of It All!

Price Dropped

Cottage

The Pleasant Hill Cottage-Storybook Luxury Near Lake Michigan & Heart Of It All!

10.0

Exceptional

(1 Review)

3 Bedrooms 2 Baths 10 Guests 1650 ft²

US $639/Night 7 Nights - US $4,472

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Cottage

Entire home, close to Ravinia Festival, Lake, Town, and Train to the city.

10.0

Exceptional

(1 Review)

3 Bedrooms 1 Bath 8 Guests

US $525/Night 7 Nights - US $3,674

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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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2-Acre Highland Park Retreat with Heated Pool ~ 5*

House

2-Acre Highland Park Retreat with Heated Pool ~ 5*

9.8

Exceptional

(9 Reviews)

6 Bedrooms 4 Baths 14 Guests 5198.97 ft²

US $648/Night 7 Nights - US $4,536

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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 Russell

4 Bedrooms 2 Baths 11 Guests 2066.67 ft²

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

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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

USS Alexandria

1 Bedroom 1 Bath 11 Guests 2066.67 ft²

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

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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

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

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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More Top-Rated Cottage Rentals in Highwood Area

Why Choose Rent By Owner for your Highwood Cottage Rentals?

What makes our Cottage Rentals 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 Cottage Rentals stay?

To make the most of your stay, consider visiting during the shoulder seasons when the area offers pleasant weather and fewer crowds, allowing you to enjoy your ideal vacation in this charming destination.

Peak Season Highlights

Summer (June to August)

During the warm months, you can enjoy the region's lively outdoor activities and scenic views, making it the perfect time to explore this destination's natural beauty.

Average Temperature Daytime: around 80°F (27°C) - Nighttime: about 65°F (18°C)

Fall (September to November)

The crisp air and vibrant foliage create an inviting atmosphere for outdoor adventures and relaxing getaways in the area’s cozy cottages.

Average Temperature Daytime: approximately 70°F (21°C) - Nighttime: roughly 50°F (10°C)

Off-Season Highlights

Winter (December to February)

This quieter period offers a peaceful setting for those seeking solitude and the chance to enjoy the area's serene winter landscape in comfort.

Average Temperature Daytime: around 35°F (2°C) - Nighttime: near 20°F (-6°C)

Spring (March to May)

As nature begins to awaken, you can experience fewer crowds while appreciating the fresh blooms and mild weather from your cottage retreat.

Average Temperature Daytime: about 60°F (15°C) - Nighttime: close to 40°F (4°C)

Weekly Weather Forecast for Highwood

How to Book Your Highwood Cottage Rentals

What's our booking process?

Our platform allows you to browse a curated selection of cottage rentals. 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 Cottage Rentals in Highwood Area

Common Cottage Rentals Amenities

What amenities can you expect?

Our Cottage Rentals 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 spacious outdoor patios or decks perfect for relaxing and entertaining during your stay in the area.
Take advantage of private gardens or yards that offer a peaceful setting for outdoor activities or dining al fresco.
Make use of outdoor grilling stations to prepare delicious meals while enjoying the fresh air in this region.
Relax by a fire pit, ideal for gathering with family or friends after a day exploring the surrounding attractions.
Access to covered porches or verandas that provide a shaded retreat on warm sunny days in this destination.
Utilize outdoor furniture like loungers and tables designed for enjoying the scenic views of the area’s natural beauty.
Benefit from nearby recreational facilities such as walking trails, bike paths, or picnic areas to enhance your outdoor experience here.

Top Attractions Around Highwood

What attractions are nearby?

Within this charming region, you can enjoy a variety of outdoor activities and cultural attractions nearby, making it an ideal destination to explore while staying in cozy cottages that offer a comfortable and convenient base for your adventures in Highwood, Illinois.

Family Activities

Highwood Recreation Center Engage in family-friendly activities such as swimming, sports, and community events at this local recreation hub.
Fort Sheridan Forest Preserve Explore scenic nature trails and enjoy outdoor picnics in this expansive natural area just outside the town center.
Highwood's Downtown Shopping District Stroll through charming shops and participate in seasonal festivals that offer fun for all ages.
Local Art Exhibits and Workshops Foster creativity with family visits to art galleries and interactive workshops held throughout the region.

Adult Activities

Visit the Highwood Public Golf Course Enjoy a relaxing day on the greens at this local golf course, perfect for honing your skills amidst scenic surroundings.
Explore the local art scene at nearby galleries Discover vibrant artworks and support regional artists in the area's charming galleries, enriching your cultural experience.
Attend live music performances: Experience live entertainment by talented musicians in the region's cozy venues, adding a lively touch to your stay.
Indulge in culinary delights at area restaurants Savor diverse cuisines and authentic flavors that reflect the region's culinary charm during your visit.

Highwood Travel Tips

How Can You Make the Most of Your Stay?

Plan Ahead Booking your stay well in advance ensures you secure the best cottages and experience a smooth arrival in this charming area.
Explore Local Events Take advantage of seasonal festivals and community gatherings to immerse yourself in the local culture during your visit.
Discover Nearby Dining Sampling regional cuisine at local eateries enhances your trip, so look for dining options close to your chosen cottage.
Utilize Transportation Options Familiarize yourself with available transit or rental services to easily explore the region and maximize your time here.

Transportation Options

Metra Train Service: Commuting via the Metra offers a convenient way to access surrounding areas from the region, making it easier for you to explore efficiently.
Local Bus Routes: The area is well-served by local bus routes that provide affordable and reliable transportation options within Highwood and nearby neighborhoods.
Taxi and Rideshare Services: Taxis and rideshare companies operate frequently here, offering a flexible and comfortable way to get around without the need for private vehicle ownership.
Car Rentals: Several car rental agencies serve the region, giving you the freedom to explore Highwood and its surroundings at your own pace during your stay.

Local Customs Options

Respect for Local Traditions: You will find that embracing community events and local festivals helps you connect with the area's cultural heritage in Highwood, Illinois.
Dining Etiquette: When visiting local eateries, it’s customary to greet staff politely and enjoy regional specialties with appreciation for the culinary traditions here.
Celebration of Seasonal Events: Participating in seasonal festivities, such as the region’s holiday parade or summer concerts, allows you to experience the vibrant community spirit firsthand.
Environmental Respect: Maintaining cleanliness and respecting outdoor spaces is a valued tradition, ensuring the natural beauty of this destination remains pristine for all visitors.

Highwood Cottage Rentals Frequently Asked Questions

1. What are the top Cottages 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 Cottages in Highwood:

2. How many Cottages are available in Highwood?

Currently, the total number of properties listed by RBO in 2026 is over 3 in the Highwood area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cottages in Highwood. 

3. What is the cancellation policy for cottages in this region?

Cancellation policies vary depending on the individual listing. To understand specific terms, please review the cancellation details on the property listing or contact the owner directly.

4. Are there any additional fees I should be aware of when booking a cottage here?

Additional fees such as cleaning charges or service fees are often listed with the property details. For precise information, check the listing or reach out to the property owner.

5. How can I ensure my booking is secure and confirmed?

Booking confirmation is typically provided once your reservation is finalized through the platform. For added assurance, verify the property's availability and contact the owner if needed before completing your reservation.

6. What amenities are usually included with cottages in this area?

Amenities vary by property but commonly include essentials like Wi-Fi, kitchen facilities, and parking. Detailed amenities are listed on each property page, so reviewing the listing will give you a clear picture.

7. Is there a minimum stay requirement for booking a cottage here?

Minimum stay requirements depend on the property and the time of year. To find out specific restrictions, refer to the listing details or contact the owner directly.