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Discover Your Perfect North Kenwood Rentals by Owner

North Kenwood Rentals by Owner

8.8 (65 Reviews)
House
Villa Dubois Guest House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
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|
10.0 (1 Review)
Apartment
LuxHome Chicago 8 mins Downtown
  • Air Conditioner
  • Parking
  • Security/Safety
View Availability
More Top-Rated Rentals by Owner in North Kenwood Area

Why Choose Rent By Owner for your North Kenwood vacation rental?

What makes our Rentals by Owner special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for North Kenwood Rentals by Owner

Where are the best neighborhoods to stay in North Kenwood?

Discover the charm of North Kenwood, Chicago, Illinois, when choosing the perfect neighborhood to stay in. This inviting area offers a blend of historic elegance and vibrant community life, making it an ideal location for your next getaway. Whether you seek peaceful residential streets or convenient access to local amenities, North Kenwood provides a welcoming environment that balances comfort with accessibility. When booking a rental by owner through Rent By Owner, you can enjoy a seamless experience in this sought-after neighborhood, ensuring a comfortable and trustworthy stay in Chicago’s dynamic landscape.

Oakland

This neighborhood offers a quiet, residential setting where you can enjoy a peaceful stay while still being close to the vibrant amenities of the region. Booking a rental here provides easy access to local streets that blend comfort with convenience in North Kenwood.

View 968+ Rentals in Oakland

Kenwood

Here, you’ll find a welcoming community atmosphere ideal for those seeking an authentic Chicago experience. Staying in this area ensures you are near some of the city’s most desirable cultural and recreational spaces, making your visit memorable.

View 26+ Rentals in Kenwood

Best Times to Visit North Kenwood

When should you plan your Rentals by Owner stay?

Choosing the right time to vacation here can enhance your experience, as the region offers distinct seasonal appeal that caters to different preferences throughout the year.

Peak Season Highlights

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Summer (June to August)

During the summer months, you'll experience warm temperatures and longer daylight hours, making it ideal for exploring the vibrant local culture and outdoor activities in this region.

Average Temperature Daytime: around 80-85°F - Nighttime: about 65-70°F
autumn
Fall (September to November)

Fall brings mild weather and beautiful autumn foliage, offering a picturesque setting to enjoy your stay while taking advantage of the area's cultural events and seasonal festivities.

Average Temperature Daytime: 65-75°F - Nighttime: about 50-60°F

Off-Season Highlights

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Winter (December to February)

Wintertime here features cooler temperatures and potential snowfall, providing a cozy atmosphere perfect for relaxing indoors or enjoying holiday celebrations.

Average Temperature Daytime: around 30-40°F - Nighttime: below freezing at about 20-30°F
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Spring (March to May)

Spring offers gradually rising temperatures and blooming landscapes, making it a quieter time to explore local neighborhoods and cultural sites without the crowds.

Average Temperature Daytime: 50-65°F - Nighttime: about 35-45°F

Weekly Weather Forecast for North Kenwood

How to Book Your North Kenwood vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. 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 North Kenwood

More Top-Rated Rentals by Owner in North Kenwood Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner 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 seating areas, perfect for relaxing after exploring the neighborhood.
  • Take advantage of private or shared patios to soak up the region's inviting atmosphere.
  • Benefit from beautifully landscaped gardens that enhance your outdoor experience here.
  • Make use of designated grilling areas or outdoor kitchens for easy meal preparation.
  • Relax in spacious yards or lawns ideal for outdoor activities and family gatherings.
  • Access nearby parks and green spaces for outdoor recreation during your stay.
  • Utilize outdoor parking options available at many rentals here within the area.

Top Attractions Around North Kenwood

What attractions are nearby?

Within this vibrant neighborhood, you can enjoy a variety of nearby activities that showcase the local culture and outdoor beauty, making your stay in North Kenwood an enriching experience.

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Family Activities

  • Chicago Children's Museum at Navy Pier: You can enjoy a day of interactive exhibits and hands-on activities designed to engage children, making it a memorable family outing close to your rental.
  • Lincoln Park Zoo: Explore this free zoo nestled nearby, where you and your family can observe a variety of animals in a fun and educational setting within the region.
  • Chicago History Museum: Dive into local history through engaging exhibits that are perfect for curious young minds eager to learn about the area's past.
  • North Pond Nature Sanctuary: Experience outdoor adventure with scenic walking trails and natural scenery, ideal for family picnics and nature walks here in the vicinity.
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Adult Activities

  • Lincoln Park Conservatory & Gardens: Explore the lush greenery and stunning plant exhibits just a short drive from here, offering a peaceful retreat in the midst of the city.
  • Magnificent Mile Shopping Experience: Indulge in upscale shopping and browse luxury boutiques along one of the region’s most iconic retail corridors.
  • Chicago Architecture River Cruise: Discover the city's architectural marvels firsthand with a guided cruise through the area’s historic and modern skyline.
  • Lakefront Trail and Beaches: Enjoy scenic walks, cycling, or relaxing on the sandy shores of Lake Michigan, all accessible from this destination’s vicinity.

Other Places to Stay in North Kenwood, IL

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North Kenwood Travel Tips

How Can You Make the Most of Your Stay?

  • Explore the Neighborhood: Wander through local streets to discover unique eateries, shops, and cultural spots that capture the authentic vibe of North Kenwood.
  • Plan Your Transportation: Take advantage of nearby public transit options or consider walkable routes to effortlessly access Chicago's attractions from your rental.
  • Utilize Local Guidance: Connect with hosts or rental owners for personalized tips on hidden gems and must-visit places within the region.
  • Respect the Community: Be mindful of neighborhood customs and stay eco-conscious to enjoy a responsible and harmonious stay in this sought-after area.

Transportation Options

  • Chicago Transit Authority (CTA) Train: You can access the city's extensive rapid transit system from here, providing quick and reliable transportation throughout Chicago, including connections to North Kenwood.
  • Bus Services: Local bus routes serve this neighborhood and surrounding areas, offering convenient options for getting around without a car.
  • Ride-Sharing Services: Popular platforms like Uber and Lyft operate seamlessly in the region, giving you flexible transportation right where you're staying.
  • Rental Cars: Many rental agencies are available near here, allowing you to explore the city and nearby attractions at your own pace with a private vehicle.

Local Customs Options

  • Respect for the Historic Homes: You’ll find that maintaining the historic charm is highly valued in this area, so appreciating and preserving the architectural heritage is considered a customary gesture.
  • Community Events and Gatherings: Participating in local events reflects the neighborhood’s friendly spirit, offering you an authentic experience during your stay here.
  • Morning Greetings: It’s common for residents to exchange friendly greetings during morning walks, showcasing the region’s welcoming atmosphere.
  • Local Dining Etiquette: When engaging with neighborhood eateries, polite dining manners are appreciated, aligning with the area's emphasis on courteous community interactions.

Frequently Asked Questions About North Kenwood Rentals by Owner

1. What are the top vacation rentals in North Kenwood?

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

2. How many Rentbyowner vacation rentals are available in North Kenwood?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 585 in the North Kenwood 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 North Kenwood. 

3. What is the cancellation policy for rental by owner properties in North Kenwood?

The cancellation policy varies by listing. To understand the specific terms, please review the details provided on the rental's page or contact the owner directly to clarify the cancellation procedures and any applicable fees.

4. How do I secure my reservation at a rental by owner in this area?

Reservations are typically confirmed through the booking platform after you complete the required payment and approval process. For additional security and to ensure your booking is valid, read the listing details carefully or reach out to the property owner with any questions.

5. Are there any house rules or restrictions I should be aware of before booking?

Yes, each rental listing includes specific house rules and restrictions set by the owner. Be sure to review these details thoroughly before confirming your reservation to ensure a smooth stay.

6. What amenities are usually included in rental by owner properties here?

Most rentals in the region offer a range of amenities such as Wi-Fi, parking, kitchen facilities, and laundry options. For exact details, please refer to the listing description or contact the owner directly.

7. Is there a minimum stay requirement for bookings in this destination?

Minimum stay requirements can vary between listings. Check each property's booking details to find out about any minimum night policies or contact the owner if you have specific dates in mind.

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More Top-Rated Rentals by Owner in North Kenwood Area