Why Choose Rent By Owner for your Highwood Cottage Rentals?
What makes our Cottage Rentals special?
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.
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.
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.
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.
Weekly Weather Forecast for Highwood
How to Book Your Highwood Cottage Rentals
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Highwood
Common Cottage Rentals Amenities
What amenities can you expect?
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:
- Near Ravinia and Navy Base, charming 3-bedroom house in peaceful Highland Park
- Spacious Home Near Lake Michigan with Peaceful Backyard
- Stunning 4-bedroom house combines comfort, elegance, and is pet-friendly
- Highwood Haven- 4 Bedroom Steps to Train station!
- Charming Lake Forest Country Estate
- Bright & Modern Home
- Safe & Secure Parkview-Sleep Sanctuary+Kitchen
- 2-Acre Highland Park Retreat with Heated Pool ~ 5*
- Serene Retreat Awaits You!
- Cozy 2 bed Apt- 2 train stops to the Naval Base!
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.


























