Discover Your Perfect Cook County Vacation Homes

Cook County Pet Friendly Vacation Rentals

10.0 (6 Reviews)
House
Stunning home in Skokie
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
See More Pet-Friendly Vacation Rentals in Cook County on PetFriendly.io

Why Choose Rent By Owner for your Cook County 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.

Best Times to Visit Cook County

When should you plan your Vacation Rentals stay?

Timing your visit to this destination allows you to experience its unique atmosphere at its best, whether you prefer the lively summer months or the quieter off-season in the region.

Peak Season Highlights

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Summer (June to August)

Experience the warm weather and vibrant atmosphere that this destination offers during the peak summer months, perfect for exploring local events and outdoor activities.

Average Temperature Daytime: high 80s to low 90s °F - Nighttime: mid 60s to low 70s °F
autumn
Fall (September to November)

Enjoy the colorful fall foliage and mild temperatures while taking advantage of the lively cultural scene in the area during this popular season among visitors.

Average Temperature Daytime: mid 60s to mid 70s °F - Nighttime: mid 40s to mid 50s °F

Off-Season Highlights

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Winter (December to February)

Visit during the colder months for fewer crowds and cozy accommodations, making it ideal if you prefer a quieter experience and lower rates here.

Average Temperature Daytime: mid 20s to mid 30s °F - Nighttime: single digits to mid 20s °F
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Spring (March to May)

Witness blooming flowers and milder weather while enjoying less busy times of the year, offering a more relaxed stay in the region.

Average Temperature Daytime: mid 50s to mid 60s °F - Nighttime: mid 30s to mid 40s °F

Weekly Weather Forecast for Cook County

How to Book Your Cook County 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 Cook County

More Top-Rated Vacation Rentals in Cook County Area

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 deck for relaxing and dining al fresco amid the scenic surroundings.
  • Take advantage of outdoor grilling amenities to cook up meals while enjoying the fresh air.
  • Make the most of landscaped gardens or yards that offer space for outdoor activities and family gatherings.
  • Benefit from shared or private outdoor pools, perfect for cooling off during warm weather in this region.
  • Utilize outdoor fire pits or fireplaces for cozy evenings under the stars.
  • Explore around the property with available walking paths or trails, ideal for outdoor exercise and exploration.
  • Secure access to outdoor parking facilities conveniently located near your vacation rental here.

Top Attractions Around Cook County

What attractions are nearby?

In this vibrant region, you can explore a variety of nearby activities, from cultural attractions to outdoor adventures, making it an ideal destination to enjoy your stay while discovering all that the area has to offer.

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Family Activities

  • Millennium Park: Discover modern art and stunning architecture while enjoying outdoor activities in this iconic park nestled in the heart of Chicago.
  • Lincoln Park Zoo: Experience a family-friendly adventure at one of the oldest zoos in the country, featuring free admission and a diverse array of wildlife exhibits.
  • The Field Museum: Engage with fascinating natural history exhibits and interactive displays that captivate visitors of all ages in this renowned museum.
  • : Explore the vibrant underwater world with engaging aquatic displays and marine life encounters at this popular family attraction.
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Adult Activities

  • Art Institute of Chicago: Explore world-renowned collections and immersive exhibitions that showcase the region's rich artistic heritage right here in this destination.
  • Millennium Park: Experience iconic public art, stunning architecture, and outdoor performances that highlight the vibrant culture of the area.
  • Navy Pier: Enjoy scenic views, entertainment options, and waterfront attractions that make for a memorable visit to this popular destination.
  • Chicago Architecture River Cruise: Discover the city's architectural marvels from a unique perspective while learning about its historic skyline along here’s famous river.

Other Places to Stay in Cook County, IL

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Cook County Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Neighborhoods: Take time to wander through the diverse neighborhoods in this region to discover hidden gems and authentic local experiences during your stay.
  • Plan for Seasonal Events: Check the calendar for seasonal festivals and events that celebrate the area's culture, offering memorable activities close to your vacation rental.
  • Maximize Your Transportation Options: Utilize available public transit or consider renting a vehicle to easily access popular attractions around here and make the most of your visit.
  • Book Strategically in Advance: Secure your preferred vacation rentals early to ensure you have the ideal home base in this destination, especially during peak travel times.

Transportation Options

  • Chicago Transit Authority (CTA) trains and buses: This reliable public transportation system connects you to key attractions and neighborhoods throughout the area, making it easy to explore without a car.
  • Metra commuter rail: Offering convenient rail services into downtown from various suburbs, it provides a comfortable way to travel for day trips or daily commutes in this region.
  • Taxi and rideshare services: Easily accessible through popular apps, these transportation options provide quick and flexible travel around the area, ideal for reaching your vacation rental or local destinations.
  • Rental cars: Renting a vehicle gives you the freedom to explore beyond the city and visit nearby attractions at your own pace, with numerous rental agencies available in town.

Local Customs Options

  • Respect for Local Festivals and Events: You’ll find that participating in or observing local festivals showcases the region’s vibrant culture and traditions during your stay.
  • Politeness and Formal Greetings: Greeting locals with a friendly "hello" and a handshake is customary when engaging with residents here, reflecting good manners valued in the area.
  • Dining Etiquette: When enjoying meals at local eateries, it’s polite to follow established dining customs, such as tipping appropriately and using utensils properly.
  • Environmental Respect: Conserving resources and respecting public spaces are important local customs that help preserve the region’s natural beauty during your visit.

Frequently Asked Questions About Cook County?

1. What are the top vacation rentals in Cook County?

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

2. How many vacation rentals have private pools in Cook County?

There are 178 vacation rentals with private pools near Cook County. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Cook County are best for families?

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

4. How many Rentbyowner vacation rentals are available in Cook County?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 8323 in the Cook County 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 Cook County. 

5. What is the cancellation policy for vacation rentals in Cook County, Illinois?

Cancellation policies vary by property, so it's important to review the specific listing details and contact the host if you have questions about refunds or cancellations.

6. Are there any house rules I should be aware of before booking?

Yes, each vacation rental will have its own set of house rules detailed in the listing. Be sure to read these carefully to ensure a smooth stay.

7. How do I find out about amenities and facilities included in a rental?

All amenities and facilities are listed in the property description. You can also contact the host directly for any special requests or clarifications.

8. Is there a minimum stay requirement for booking here?

Minimum stay requirements depend on the property and season. Check the listing details for specific information or contact the owner for confirmation.

9. What are the check-in and check-out procedures for vacation rentals in this area?

Check-in and check-out instructions are provided in the reservation details. If you need further guidance, reach out directly to the host for assistance.