Best Vacation Homes in Cook County
Apartment
10.0(2 Reviews)
1 Bedroom
1 Bath
2 Guests
700 ft²
Balcony/Terrace
Kitchen
Parking
Air Conditioner
US $74/Night
7 Nights - US $518
Apartment
10.0(14 Reviews)
1 Bedroom
1 Bath
2 Guests
699.65 ft²
Internet
Child Friendly
US $256/Night
7 Nights - US $1,792
Bed & Breakfast
10.0(517 Reviews)
1 Bedroom
1 Bath
Fireplace/Heating- Balcony/Terrace
- Parking
- Air Conditioner
US $339/Night
7 Nights - US $2,375
New
House
10.0(1 Review)
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
Pet Friendly- Kitchen
- Air Conditioner
US $762/Night
7 Nights - US $5,334
Apartment
10.0(12 Reviews)
1 Bedroom
1 Bath
4 Guests
452.08 ft²
Private Pool
Oceanfront- Fireplace/Heating
Pool
US $117/Night
7 Nights - US $819
New
Apartment
10.0(1 Review)
2 Bedrooms
1 Bath
3 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $247/Night
7 Nights - US $1,727
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $136/Night
7 Nights - US $950
New
Apartment
4 Bedrooms
4 Baths
10 Guests
1600 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,128/Night
7 Nights - US $7,897
Cook County Luxury Rentals
House
6 Bedrooms
2 Baths
7 Guests
- Air Conditioner
- Internet
Laundry
Security/Safety
Unlock the Best Price
New
Hotel
3 Baths
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
Unlock the Best Price
Apartment
2 Bedrooms
2 Baths
8 Guests
1205.56 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $6,350/Night
7 Nights - US $44,450
Bed & Breakfast
8 Bedrooms
8 Baths
16 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $5,106/Night
7 Nights - US $35,741
Apartment
8.0(1 Review)
1 Bedroom
2 Baths
8 Guests
- Pet Friendly
- Parking
- Air Conditioner
- Internet
US $4,500/Night
7 Nights - US $31,500
House
10.0(33 Reviews)
5 Bedrooms
5 Baths
14 Guests
7000 ft²
- Oceanfront
- Fireplace/Heating
Ocean View- Balcony/Terrace
US $3,828/Night
7 Nights - US $26,793
Condo
10.0(3 Reviews)
10 Bedrooms
9 Baths
16 Guests
3337 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $3,801/Night
7 Nights - US $26,608
Cook County Pet Friendly Vacation Rentals
New
Apartment
5 Bedrooms
2 Baths
12 Guests
23681 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $1,119/Night
7 Nights - US $7,831
Apartment
10.0(8 Reviews)
2 Bedrooms
1 Bath
4 Guests
914.93 ft²
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $618/Night
7 Nights - US $4,329
Bed & Breakfast
7.8(642 Reviews)
1 Bedroom
1 Bath
- Pet Friendly
- Parking
- Internet
- Security/Safety
US $223/Night
7 Nights - US $1,564
New
Apartment
1 Bedroom
3 Baths
12 Guests
1500 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
View
US $938/Night
7 Nights - US $6,563
Apartment
10.0(5 Reviews)
3 Bedrooms
2 Baths
5 Guests
1345.49 ft²
- Balcony/Terrace
- Pet Friendly
- Parking
- Air Conditioner
US $284/Night
7 Nights - US $1,991
New
House
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $707/Night
7 Nights - US $4,952
New
Apartment
2 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $600/Night
7 Nights - US $4,201
Apartment
4 Bedrooms
1 Bath
9 Guests
1200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $369/Night
7 Nights - US $2,583
Cook County Large Vacation Homes
House
4 Bedrooms
5 Baths
10 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $906/Night
7 Nights - US $6,340
Villa
10.0(5 Reviews)
4 Bedrooms
2 Baths
7 Guests
1097.92 ft²
- Pet Friendly
- Parking
- Air Conditioner
- Child Friendly
US $232/Night
7 Nights - US $1,624
US $507/Night
7 Nights - US $3,551
New
House
4 Bedrooms
3 Baths
10 Guests
Hot Tub- Fireplace/Heating
- Air Conditioner
- Internet
US $738/Night
7 Nights - US $5,166
Apartment
10.0(4 Reviews)
13 Bedrooms
12 Baths
32 Guests
1435.19 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $1,582/Night
7 Nights - US $11,076
New
House
4 Bedrooms
3 Baths
12 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $672/Night
7 Nights - US $4,705
New
Apartment
4 Bedrooms
2 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Air Conditioner
- Internet
US $419/Night
7 Nights - US $2,930
House
1 Bedroom
2 Baths
10 Guests
132 ft²
- Kitchen
- Air Conditioner
- Internet
- Laundry
US $363/Night
7 Nights - US $2,539
Why Choose Rent By Owner for your Cook County 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 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
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
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
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
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
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.
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.
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
Chicago
Chicago
Central Chicago
Downtown Chicago
West Side
The Loop
Near North Side
North Side
River North
South Loop
South Side
Far North Side
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.
Cook County Vacation Rental Frequently Asked Questions
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:
- The Sono Chicago
- 52nd Floor MagMile Penthouse Views Fireplace Pool
- Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
- 55th Floor Penthouse with Award-Winning Views
- Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach
- 53 Floor MagMile Penthouse Views, Balcony, Pool
- 51st Floor MagMile Penthouse Views Balcony Pool
- NEW LUXURY PENTHOUSE CONDO
- 2-Story Penthouse Views, Fireplace, Pool, Gym
- Great Location-Beautiful Friendly Andersonville Neighborhood
2. How many vacation rentals have private pools in Cook County?
There are 185 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 2026 is over 9871 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.
Cook County Top Rated Vacation Rentals
Apartment
10.0(412 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $551/Night
7 Nights - US $3,855
Apartment
10.0(311 Reviews)
3 Bedrooms
2 Baths
8 Guests
2200 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $1,690/Night
7 Nights - US $11,830
Apartment
10.0(245 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $613/Night
7 Nights - US $4,294
Apartment
10.0(229 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $517/Night
7 Nights - US $3,616
Apartment
10.0(213 Reviews)
2 Bedrooms
3 Baths
8 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $1,237/Night
7 Nights - US $8,656
Apartment
10.0(201 Reviews)
2 Bedrooms
2 Baths
7 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $1,203/Night
7 Nights - US $8,422
Apartment
10.0(66 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $428/Night
7 Nights - US $2,995
Apartment
10.0(42 Reviews)
3 Bedrooms
2 Baths
7 Guests
1400 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $599/Night
7 Nights - US $4,191
