Discover Your Perfect Essex Vacation Homes

Why Choose Rent By Owner for your Essex Vacation Rental Homes?

What makes our Vacation Rentals special?

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

Popular Areas for Essex Vacation Rentals

Where are the best neighborhoods to stay in Essex?

When planning your stay in Essex, Chicago, Illinois, exploring the neighborhood options can help you find the perfect location for your visit. Whether you're looking to experience the vibrant city life or enjoy a more relaxed, residential atmosphere, neighborhoods in this area offer a variety of options to suit your preferences. Staying in a well-connected part of Chicago allows for easy access to local attractions and amenities, ensuring a convenient and enjoyable trip. With a wide selection of reliable vacation rentals available, you can choose a neighborhood that fits your style and needs, making your experience in Essex, Chicago, truly memorable.

Greater Grand Crossing

This neighborhood offers a rich local atmosphere, perfect for those seeking an authentic Chicago experience. Staying here places you in a vibrant community with easy access to the city's key attractions.

View 471+ Rentals in Greater Grand Crossing

Avalon Park

Here, you can enjoy a welcoming neighborhood that combines suburban charm with the convenience of city living. It’s an ideal area for discovering a peaceful retreat while remaining connected to all that Chicago offers.

View 201+ Rentals in Avalon Park

Best Times to Visit Essex

When should you plan your Vacation Rentals stay?

Choosing the ideal time to visit here can enhance your experience, as this destination offers distinct attractions and weather patterns throughout the year that are perfect for planning your stay in the area.

Peak Season Highlights

summer
Summer (June to August)

During the summer months, this area experiences warm weather and long daylight hours, making it ideal for outdoor activities and exploring local attractions.

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

Autumn brings mild temperatures and vibrant foliage, creating a picturesque setting for your stay and outdoor adventures in the region.

Average Temperature Daytime: approximately 70°F - Nighttime: roughly 50°F

Off-Season Highlights

image
Winter (December to February)

While winter can be chilly, this time offers a quieter experience with fewer crowds, perfect for those seeking a more relaxed visit here.

Average Temperature Daytime: about 40°F - Nighttime: around 25°F
image
Spring (March to May)

Spring sees moderate temperatures and blooming landscapes, providing a comfortable atmosphere for enjoying this destination’s natural beauty without the peak-season crowds.

Average Temperature Daytime: roughly 60°F - Nighttime: approximately 40°F

Weekly Weather Forecast for Essex

How to Book Your Essex 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 Essex

More Top-Rated Vacation Rentals in Essex 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 outdoor seating areas such as patios or decks, perfect for relaxing and dining al fresco.
  • Take advantage of landscaped gardens or yards to unwind amidst greenery in this vibrant region.
  • Make the most of private or shared outdoor pools to cool off during warm weather months.
  • Benefit from outdoor grilling stations or barbecue setups for memorable cookouts with family and friends.
  • Experience the convenience of nearby walking trails or scenic pathways located within the area.
  • Utilize outdoor recreational facilities like sports courts or playgrounds available at select properties.
  • Access outdoor fire pits or fireplaces ideal for cozy evenings under the stars in this destination’s inviting setting.

Top Attractions Around Essex

What attractions are nearby?

Enjoy a variety of outdoor activities, cultural experiences, and local attractions just moments from your Essex stay in Chicago, Illinois, allowing you to explore the vibrant region at your own pace.

image
image

Family Activities

  • Lincoln Park Zoo: Enjoy a family day at this renowned zoo in Chicago, where you can observe a variety of animals in naturalistic habitats for free.
  • Museum of Science and Industry: Explore interactive exhibits and hands-on activities that make learning fun for children of all ages in the heart of the city.
  • Experience scenic boat rides, rides, and entertainment options along the lakeshore, perfect for entertaining young and older kids alike.
  • Discover marine life through immersive exhibits and engaging displays at one of the region’s top aquariums.
image

Adult Activities

  • Chicago Museum Campus: Explore the area’s cultural heart with world-class museums and stunning lakefront views, perfect for enriching your visit to this vibrant city.
  • Lincoln Park Zoo: Enjoy a leisurely day at one of the oldest zoos in North America, offering close encounters with diverse wildlife amidst scenic park surroundings.
  • The Magnificent Mile: Indulge in upscale shopping, fine dining, and scenic architecture along this iconic stretch that epitomizes urban elegance in the region.
  • Lake Michigan Beaches: Relax or engage in water activities on the pristine sands along the lakeshore, providing a perfect escape within the city’s boundaries.

Other Places to Stay in Essex, IL

ETA Creative Arts Foundation
ETA Creative Arts Foundation Vacation Rentals
More Places to Stay Near Essex

Essex Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Cuisine: Take advantage of the area's renowned dining options to experience authentic flavors unique to here.
  • Visit Popular Neighborhoods: Spend time wandering through vibrant neighborhoods to discover hidden gems and local culture.
  • Plan Outdoor Activities: Utilize the region's parks and scenic spots for outdoor adventures that showcase its natural beauty.
  • Book in Advance: Secure your preferred vacation rentals early to ensure a comfortable stay amid the area's high demand during peak seasons.

Transportation Options

  • Chicago Transit Authority (CTA) Trains and Buses: The CTA provides extensive train and bus services that make exploring the city and nearby areas convenient and affordable.
  • Metra Commuter Rail: For traveling between the suburbs and downtown, Metra offers reliable rail connections that connect local neighborhoods with Chicago’s core attractions.
  • Taxi and Rideshare Services: Popular options like taxis and rideshare apps such as Uber and Lyft offer flexible transportation within the region for quick trips and airport transfers.
  • Car Rentals: Renting a car provides the freedom to explore beyond the city limits at your own pace, especially for visits to surrounding natural or recreational sites.

Local Customs Options

  • Greeting Etiquette: When visiting here, it’s customary to greet locals with a warm smile and a firm handshake, reflecting the region’s friendly and welcoming spirit.
  • Dining Customs: Embrace the local dining traditions by enjoying hearty, comfort foods that highlight the area's culinary heritage, often shared in casual, communal settings.
  • Dress Code: Casual yet polished attire is typical for daytime outings, while more refined clothing might be appreciated for dinner or special occasions within the community.
  • Community Events: Participating in neighborhood festivals and local gatherings offers an authentic experience and a chance to connect with the area's cultural roots.

Frequently Asked Questions About Essex?

1. What are the top vacation rentals in Essex?

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

2. Which vacation homes in Essex are best for families?

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

3. How many Rentbyowner vacation rentals are available in Essex?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 502 in the Essex 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 Essex. 

4. What is the cancellation policy for vacation rentals in Essex near Chicago?

The cancellation policy varies depending on the individual property listing. You should review the specific terms outlined in each rental's listing details or contact the property owner directly to understand the cancellation and refund options available.

5. How can I confirm availability for a vacation rental in this area?

Availability is updated regularly by property owners, so it’s best to check the booking calendar on the listing or reach out directly to the owner for the most accurate and current information.

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

Each vacation rental may have its own set of house rules, such as pet policies or noise restrictions. These details are typically included in the listing description, but contacting the owner ensures you have all necessary information before confirming your reservation.

7. What amenities are usually included in vacation rentals near Chicago?

Amenities vary from property to property, but common features include Wi-Fi, kitchen facilities, and parking. Review the listing specifics or contact the owner to confirm the amenities offered at your chosen rental.

8. How do I inquire about special requests or add-ons for my stay?

You can send a message through the booking platform to communicate directly with the property owner regarding any special requests or additional services you may need during your stay in the region.