Best Vacation Homes in Highwood
Cottage
10.0(27 Reviews)
2 Bedrooms
1 Bath
6 Guests
Fireplace/Heating
Ocean View
Balcony/Terrace
View
US $331/Night
7 Nights - US $2,318
House
9.8(9 Reviews)
6 Bedrooms
4 Baths
14 Guests
5198.97 ft²
Oceanfront
Pool- Ocean View
- View
US $648/Night
7 Nights - US $4,536
House
10.0(1 Review)
2 Bedrooms
2 Baths
2 Guests
Hot Tub- Fireplace/Heating
- Balcony/Terrace
Pet Friendly
US $286/Night
7 Nights - US $2,005
Apartment
4 Bedrooms
2 Baths
11 Guests
2066.67 ft²
- Fireplace/Heating
- Pet Friendly
Air Conditioner
Internet
US $542/Night
7 Nights - US $3,794
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
Kitchen- Air Conditioner
US $115/Night
7 Nights - US $806
Apartment
9.4(3 Reviews)
2 Bedrooms
1 Bath
7 Guests
743 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
Parking
US $279/Night
7 Nights - US $1,951
Apartment
8.4(7 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $190/Night
7 Nights - US $1,328
Apartment
8.0(4 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $174/Night
7 Nights - US $1,217
Highwood Luxury Rentals
House
4 Bedrooms
4 Baths
8 Guests
- Hot Tub
- Fireplace/Heating
- Kitchen
- Air Conditioner
US $3,210/Night
7 Nights - US $22,468
House
10.0(2 Reviews)
6 Bedrooms
4 Baths
12 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $1,230/Night
7 Nights - US $8,612
House
10.0(4 Reviews)
5 Bedrooms
4 Baths
10 Guests
5000 ft²
- Air Conditioner
- Internet
Child Friendly
Laundry
US $1,012/Night
7 Nights - US $7,087
House
10.0(1 Review)
4 Bedrooms
5 Baths
7 Guests
- Hot Tub
- Fireplace/Heating
- Air Conditioner
- Internet
US $763/Night
7 Nights - US $5,341
Cottage
3 Bedrooms
2 Baths
10 Guests
1650 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $651/Night
7 Nights - US $4,555
House
9.6(51 Reviews)
4 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $556/Night
7 Nights - US $3,893
House
10.0(6 Reviews)
3 Bedrooms
4 Baths
7 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $550/Night
7 Nights - US $3,850
Apartment
1 Bedroom
1 Bath
11 Guests
2066.67 ft²
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $537/Night
7 Nights - US $3,761
Highwood Pet Friendly Vacation Rentals
Apartment
2 Bedrooms
1 Bath
7 Guests
700 ft²
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $169/Night
7 Nights - US $1,182
Apartment
2 Bedrooms
1 Bath
7 Guests
753.47 ft²
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $305/Night
7 Nights - US $2,133
Apartment
10.0(1 Review)
4 Bedrooms
2 Baths
11 Guests
2067 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $410/Night
7 Nights - US $2,871
House
1 Bedroom
2 Baths
8 Guests
129.17 ft²
- Pet Friendly
- Air Conditioner
- Internet
- Child Friendly
US $529/Night
7 Nights - US $3,703
House
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
1320 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $291/Night
7 Nights - US $2,040
Apartment
1 Bedroom
1 Bath
11 Guests
2067 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $448/Night
7 Nights - US $3,137
House
4 Bedrooms
2 Baths
9 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $394/Night
7 Nights - US $2,757
Apartment
4 Bedrooms
2 Baths
11 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $247/Night
7 Nights - US $1,726
Highwood Large Vacation Homes
Apartment
4 Bedrooms
1 Bath
11 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $202/Night
7 Nights - US $1,412
House
9.0(2 Reviews)
6 Bedrooms
5 Baths
12 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $959/Night
7 Nights - US $6,714
House
8.0(1 Review)
4 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $865/Night
7 Nights - US $6,054
House
6.0(2 Reviews)
4 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Air Conditioner
US $999/Night
7 Nights - US $6,993
House
4 Bedrooms
4 Baths
10 Guests
3000 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $563/Night
7 Nights - US $3,943
House
10.0(1 Review)
6 Bedrooms
5 Baths
12 Guests
- Hot Tub
Spa- Fireplace/Heating
- Pet Friendly
US $683/Night
7 Nights - US $4,781
House
8.4(6 Reviews)
4 Bedrooms
3 Baths
12 Guests
1800 ft²
- Pet Friendly
- Internet
- Child Friendly
- Laundry
US $612/Night
7 Nights - US $4,284
Why Choose Rent By Owner for your Highwood Vacation Rental Homes?
What makes our Vacation 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 Vacation Rentals stay?
Choosing the right time to vacation here can enhance your experience, as the area's climate and local events vary throughout the year, making it important to plan accordingly for a memorable stay in Highwood, Illinois.
Peak Season Highlights
Summer (June to August)
During the warm summer months, this destination experiences lively outdoor activities and community events, making it an ideal time to visit and enjoy your vacation rentals.
Average Temperature Daytime: around 80°F - Nighttime: around 65°F
Early Fall (September to October)
The early fall season offers pleasant weather and beautiful foliage, perfect for exploring the area and relaxing in well-appointed vacation rentals.
Average Temperature Daytime: around 70°F - Nighttime: around 50°F
Off-Season Highlights
Late Fall and Winter (November to February)
Experience a quieter period with cooler temperatures, ideal for those seeking a peaceful retreat in cozy vacation rentals away from peak crowds.
Average Temperature Daytime: around 40°F - Nighttime: around 25°F
Early Spring (March to May)
As the region transitions into spring, the weather begins to warm but remains relatively mild, offering an off-peak opportunity to enjoy the local scenery and comfortable accommodations.
Average Temperature Daytime: around 55°F - Nighttime: around 35°F
Weekly Weather Forecast for Highwood
How to Book Your Highwood Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Highwood
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation 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 outdoor dining areas perfect for meals under the sun.
- Relax in private or shared patios that offer a peaceful escape.
- Make use of outdoor grills for cookouts and barbecues.
- Take advantage of spacious yards ideal for outdoor activities and games.
- Benefit from shaded areas such as pergolas or gazebos for comfort during warm days.
- Utilize outdoor seating arrangements designed for socializing and relaxing.
- Experience scenic views from balconies or decks overlooking the region’s natural beauty.
Top Attractions Around Highwood
What attractions are nearby?
Within this charming area, you can enjoy a variety of outdoor activities and local events that showcase the best of the region's vibrant community and scenic surroundings.
Family Activities
- Highwood Recreation Center: Engage in family-friendly activities and indoor sports at this community hub, perfect for keeping everyone active during your stay.
- Highwood Historical Society Museum: Discover local history through engaging exhibits, offering an educational experience that connects you to the area's rich cultural heritage.
- Village Green Park: Enjoy outdoor picnics, playground fun, and scenic strolls in this picturesque park situated conveniently in the region.
- Local Dining Experiences: Savor diverse culinary options nearby, making it easy to indulge in family meals within the welcoming atmosphere of this destination.
Adult Activities
- Enjoy the vibrant arts scene: Explore local galleries and theaters that showcase the region’s creative spirit, perfect for enriching your cultural experience here.
- Visit local breweries and pubs: Savor craft beers at popular establishments that highlight the area's brewing traditions, ideal for relaxing evenings after your day of exploring.
- Take a scenic walk or bike ride: Discover charming neighborhoods and parks with picturesque views, offering a refreshing way to see the best of this destination.
- Attend community events and festivals: Participate in seasonal celebrations and markets that capture the lively essence of this region's local culture and hospitality.
Highwood Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Local Events: Check the area's event calendar to align your stay with local festivals or celebrations, enhancing your experience of this vibrant destination.
- Explore Nearby Dining Options: Take advantage of the region’s diverse restaurants and cafes to enjoy authentic flavors without straying far from your vacation rental.
- Utilize Public Transportation: Familiarize yourself with the local transit options to easily navigate the area and access popular attractions nearby.
- Book Your Accommodation Early: Secure your ideal vacation rental in this destination well in advance to ensure availability during peak travel times.
Transportation Options
- Metra Train Service: This regional rail system offers convenient transportation into Chicago and surrounding areas, making it ideal for exploring the region from your Highwood vacation rental.
- Local Bus Routes: Multiple bus services connect here to nearby neighborhoods and major transit hubs, providing an affordable and reliable way to get around during your stay.
- Taxi and Rideshare Services: Taxis and popular rideshare options like Uber and Lyft are readily available in this area, offering flexible door-to-door transportation for visitors seeking convenience.
- Car Rental Agencies: Several local and airport-based car rental companies provide the flexibility to explore the region at your own pace, straight from your Highwood accommodation.
Local Customs Options
- Local Art Scene: Embrace the vibrant tradition of local art galleries in the region, showcasing highwood's rich artistic heritage.
- Community Festivals: Participate in annual community festivals that celebrate Highwood’s cultural diversity and historic roots.
- Dining Etiquette: Experience the area's culinary customs, where sharing hearty meals with neighbors is a cherished tradition.
- Historic Respect: Respect the preservation efforts of historic buildings in the region, reflecting its commitment to maintaining local charm.
Highwood Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals 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 Vacation Rentals in Highwood:
- Re-imagined 1880's cottage walking distance to Highwood, Metra, Lake Michigan
- Near Ravinia and Navy Base, charming 3-bedroom house in peaceful Highland Park
- Spacious Home Near Lake Michigan with Peaceful Backyard
- Sunset Manor: Opulent Mansion, Ultimate Serenity Awaits
- Stunning 4-bedroom house combines comfort, elegance, and is pet-friendly
- Highwood Haven- 4 Bedroom Steps to Train station!
- Bright & Modern Home
- Charming Lake Forest Country Estate
- Safe & Secure Parkview-Sleep Sanctuary+Kitchen
- 2-Acre Highland Park Retreat with Heated Pool ~ 5*
2. Which vacation homes in Highwood are best for families?
If you are looking for a family-friendly vacation home in Highwood, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Highwood:
3. How many Rentbyowner vacation rentals are available in Highwood?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 39 in the Highwood area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Highwood.
4. What is the cancellation policy for vacation rentals in this area?
The cancellation policy varies depending on the individual property listing. To find out the specific details, please review the cancellation terms listed on the property page or contact the property owner directly before confirming your booking.
5. Are pets allowed in vacation rentals here?
Pet policies differ among the vacation rentals available in this region. Be sure to check the specific property's pet restrictions and any associated fees by reviewing the listing details or contacting the host.
6. How do I know if a vacation rental in this destination is suitable for families?
Many listings specify whether they are family-friendly and include amenities suitable for children. Always read the property description carefully and reach out to the owner if you have special requirements to ensure the rental meets your needs.
7. What are the check-in and check-out times for rentals in this part of Illinois?
Check-in and check-out times are set by each property owner and can vary. Details are provided on the listing page, but you should confirm these times directly with the host to ensure a smooth arrival and departure.
8. Is there parking available at vacation rentals in this city?
Parking availability varies by property. Some rentals offer private parking spaces, while others may rely on street parking. Verify the parking arrangements listed in the property details or ask the owner when making your reservation.
