Discover Your Perfect North Kenwood Vacation Homes

North Kenwood Luxury Rentals

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9.0 (271 Reviews)
Hotel
Sophy Hyde Park
  • Air Conditioner
  • Parking
  • Pet Friendly
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North Kenwood Pet Friendly Vacation Rentals

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Why Choose Rent By Owner for your North Kenwood Vacation Rental Homes?

What makes our Vacation Rentals 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 Vacation Rentals

Where are the best neighborhoods to stay in North Kenwood?

When selecting a neighborhood to stay in North Kenwood, Chicago, Illinois, you’ll find an area rich in history and charm. Located near some of the city’s most desirable attractions, this neighborhood offers a peaceful retreat while keeping you close to vibrant city life. Whether you're seeking a quiet residential setting or convenient access to bustling local hotspots, North Kenwood provides a variety of options for your accommodations. Exploring this neighborhood will give you an authentic Chicago experience, complemented by the comfort and convenience of well-suited vacation rentals designed to meet your travel needs.

Oakland

In Oakland, you can enjoy a peaceful atmosphere close to the vibrant attractions of the city, making it an ideal spot for your stay in this region. The area offers convenient access to local amenities, enhancing your experience when exploring Chicago from here.

View 968+ Rentals in Oakland

Kenwood

Kenwood provides a charming residential setting with easy access to cultural and recreational sites, perfect for those seeking a comfortable base in this part of Chicago. Staying in this neighborhood allows you to immerse yourself in the local ambiance while remaining connected to the city's highlights.

View 172+ Rentals in Kenwood

Best Times to Visit North Kenwood

When should you plan your Vacation Rentals stay?

Choosing the right time to visit here can significantly enhance your experience, as this destination offers unique seasonal appeal that suits a variety of travel preferences throughout the year.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

This is when the region experiences warm temperatures and increased outdoor activities, making it an ideal time to explore local attractions and enjoy pleasant weather.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 70°F
autumn
Early Fall (September to October)

During these months, the area sees mild temperatures and fewer crowds, providing a comfortable environment for sightseeing and outdoor adventures.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 55°F to 65°F

Off-Season Highlights

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Mid Winter (January to February)

The coldest period of the year brings lower temperatures, but it offers a peaceful setting with fewer visitors seeking cozy indoor escapes or cultural experiences.

Average Temperature Daytime: 30°F to 40°F - Nighttime: 20°F to 30°F
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Late Fall (November to December)

As temperatures drop and holiday preparations begin, fewer travelers visit. This is a good time to find deals on vacation rentals and enjoy a quieter atmosphere.

Average Temperature Daytime: 40°F to 50°F - Nighttime: 30°F to 40°F

Weekly Weather Forecast for North Kenwood

How to Book Your North Kenwood 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 North Kenwood

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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 a private outdoor patio or balcony, perfect for relaxing and taking in the fresh air
  • Take advantage of a well-maintained backyard area for outdoor dining or leisure activities
  • Experience convenient access to nearby parks and green spaces for outdoor recreation
  • Make the most of an outdoor grill or BBQ facility for summertime cookouts
  • Utilize on-site bicycle storage or rental options to explore the local neighborhood
  • Relax in a shared garden or landscaped yard designed for outdoor enjoyment
  • Benefit from proximity to walking trails or scenic routes ideal for outdoor excursions

Top Attractions Around North Kenwood

What attractions are nearby?

Within this vibrant neighborhood, you can explore a variety of cultural landmarks and outdoor activities that highlight the charm of North Kenwood, Chicago, Illinois, USA, making your stay both engaging and memorable.

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Family Activities

  • Chicago Botanic Garden: Explore this expansive garden with your family, offering lush landscapes and engaging nature exhibits just a short drive from the area.
  • Museum of Science and Industry: Engage your children with interactive exhibits and hands-on activities that make learning about science fun and memorable here in Chicago.
  • : Visit this free zoo nestled in the city's iconic park, providing an entertaining day for families to see a wide variety of animals.
  • Adjacent Lake Michigan Beaches: Spend a relaxing day on the sandy shores along the lake in nearby Chicago, perfect for picnics, swimming, and outdoor play with loved ones.
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Adult Activities

  • Chicago Museum of Science and Industry: Explore engaging exhibits and interactive displays that appeal to adults seeking educational and entertaining experiences in the area.
  • Lake Michigan Beaches: Relax and unwind along the scenic shoreline with stunning views and opportunities for kayaking or sunbathing just minutes from your stay.
  • Hyde Park Jazz Festival: Attend this renowned cultural event featuring talented jazz musicians, perfect for music lovers visiting here for a memorable experience.
  • Beverly Arts Center: Discover enriching performances, art exhibitions, and cultural programs designed to cater to those interested in the region’s vibrant arts scene.

Other Places to Stay in North Kenwood, IL

Muddy Waters’ House
Muddy Waters’ House Vacation Rentals
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North Kenwood Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Dining Options: Discover authentic eateries and cafes nearby to enjoy the regional flavors unique to this destination.
  • Utilize Public Transportation: Take advantage of accessible transit options in the area to conveniently explore the neighborhood and beyond.
  • Plan Nearby Activities: Schedule visits to local parks, cultural sites, or community events to enrich your stay in this vibrant part of Chicago.
  • Choose a Well-Located Vacation Rental: Select accommodations that put you close to key attractions and transportation hubs for a seamless experience here.

Transportation Options

  • Chicago Transit Authority (CTA) Trains: The extensive CTA train system offers convenient access to various parts of the city from North Kenwood, making it easy to explore without the need for a car.
  • Bus Services: Local bus routes serve this neighborhood directly, providing affordable and reliable transportation within the area and connecting you to other neighborhoods in Chicago.
  • Divvy Bicycle Share: The bike-sharing program provides an eco-friendly way to navigate here at your own pace, with numerous stations conveniently located around the region.
  • Taxis and Rideshare Services: Taxis and popular rideshare options like Uber and Lyft are readily available, offering door-to-door service tailored to your schedule within the area.

Local Customs Options

  • Respect for Local Hospitality: Visitors often find that welcoming gestures and courteous interactions are highly valued in the area, reflecting the community’s friendly spirit.
  • Celebration of Cultural Events: Participating in or observing local festivals and parades showcases the region’s rich cultural traditions and lively community gatherings.
  • Dining Etiquette: When dining here, it’s customary to appreciate the diverse culinary influences, with a focus on politeness and shared dishes during communal meals.
  • Neighborhood Respect: Maintaining a considerate attitude towards neighbors by following noise ordinances and respecting property boundaries is an important aspect of daily life here.

Frequently Asked Questions About North Kenwood?

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 vacation rentals have private pools in North Kenwood?

There are 2 vacation rentals with private pools near North Kenwood. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in North Kenwood are best for families?

If you are looking for a family-friendly vacation home in North Kenwood, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in North Kenwood:

4. 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 674 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. 

North Kenwood Top Rated Vacation Rentals

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