Discover Your Perfect East Side Vacation Homes

East Side Luxury Rentals

New
Apartment
Luxury off the Lake
  • Air Conditioner
  • Pet Friendly
  • Bedding/Linens
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Find More East Side Villas, Resorts, & Rentals on BedroomVillas

East Side Pet Friendly Vacation Rentals

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8.4 (8 Reviews)
Apartment
Charming 3BD 2BTH Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
See More Pet-Friendly Vacation Rentals in East Side on PetFriendly.io

Why Choose Rent By Owner for your East Side 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 East Side

When should you plan your Vacation Rentals stay?

Timing your visit to this destination can enhance your experience, so consider the climate and local events to select the perfect season for booking your vacation rentals in East Side, Chicago, Illinois, USA.

Peak Season Highlights

summer
Late Spring to Summer (May to August)

During these months, you'll experience warm weather ideal for exploring the region’s outdoor activities and events. This is the most popular time to visit, so booking early ensures you secure the best vacation rentals in the area.

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

This period offers mild temperatures and fewer crowds, making it perfect for enjoying the scenic beauty and local festivities. Lock in your accommodations now to enjoy the vibrant season comfortably.

Average Temperature Daytime: 70°F to 78°F - Nighttime: 55°F to 63°F

Off-Season Highlights

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Winter (December to February)

The colder months bring fewer visitors, which means more availability and potentially better rates on vacation rentals here. It's a peaceful time to explore the quieter side of this destination.

Average Temperature Daytime: 30°F to 40°F - Nighttime: 20°F to 30°F
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Early Spring (March to April)

As the region transitions out of winter, off-peak rates are common, and you can enjoy the emerging spring scenery without the summer crowds. Planning ahead allows you to find exceptional rental options at competitive prices.

Average Temperature Daytime: 45°F to 58°F - Nighttime: 35°F to 45°F

Weekly Weather Forecast for East Side

How to Book Your East Side 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 East Side

More Top-Rated Vacation Rentals in East Side 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 perfect for relaxing or dining al fresco amid the scenic surroundings.
  • Take advantage of private gardens or yards to unwind and experience the area's natural beauty firsthand.
  • Make the most of nearby parks or green spaces for walking, jogging, or picnicking just steps from your rental.
  • Benefit from outdoor grilling facilities that allow you to prepare delicious meals while enjoying the fresh air.
  • Access patios or decks with panoramic views that showcase the region’s unique skyline or waterfront scenery.
  • Utilize outdoor recreational equipment such as bikes or sports gear often available for exploring the neighborhood.
  • Discover easy access to walking paths or bike trails that highlight the charm and natural landscape of this destination.

Top Attractions Around East Side

What attractions are nearby?

When staying here, you can enjoy a variety of activities nearby, including exploring local parks, experiencing cultural attractions, and discovering vibrant dining options that showcase the region's unique character.

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Family Activities

  • Chicago Children's Museum: Engage your family with hands-on exhibits and interactive displays that make learning fun for kids visiting the East Side area.
  • Lakefront Trail: Enjoy a scenic stroll, bike ride, or picnic along this picturesque trail, offering stunning views of Lake Michigan perfect for family outings.
  • Adler Planetarium: Discover the wonders of the universe together at one of the oldest planetariums in the Western Hemisphere, just minutes from here.
  • Grant Park: Relax and play in this expansive downtown park nearby, ideal for family picnics, outdoor games, and enjoying summer festivals.
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Adult Activities

  • Visit the Museum of Science and Industry Chicago: Engage your curiosity at this renowned museum, which offers interactive exhibits and immersive experiences right in the heart of the region.
  • Explore the Chicago Lakefront Trail: Take a scenic walk or bike ride along the picturesque shoreline, enjoying stunning views of Lake Michigan and the city skyline.
  • Discover local history at the South Shore Cultural Center: Immerse yourself in cultural events, art exhibitions, and historic architecture within this vibrant community hub.
  • Dine at waterfront restaurants: Savor a variety of culinary delights at dining spots overlooking the lake, perfect for relaxing after a day of exploring the area.

Other Places to Stay in East Side, IL

Calumet Beach
Calumet Beach Vacation Rentals
Munson Beach
Munson Beach Vacation Rentals
Irondale
Irondale Vacation Rentals
Calumet Park
Calumet Park Vacation Rentals
More Places to Stay Near East Side

East Side Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Cuisine: Take time to discover the area's renowned eateries and food markets to experience authentic flavors unique to East Side, Chicago.
  • Plan Your Transportation: Utilize nearby public transit options or rent a bike to easily navigate the region and visit popular attractions hassle-free.
  • Discover Off-the-Beaten-Path Spots: Venture beyond the main attractions to uncover hidden gems and local favorites that provide an authentic taste of the neighborhood.
  • Book in Advance: Secure your vacation rentals early to ensure availability and get the best deals, especially during peak travel seasons here.

Transportation Options

  • Chicago Transit Authority (CTA) Rail System: The CTA provides convenient access to the city’s key attractions and neighborhoods, making it easy for you to explore from your vacation rental.
  • Metra Commuter Rail: This regional train service connects the area to downtown Chicago and beyond, offering a reliable transportation option for day trips or commuting.
  • Bus Services: Local bus routes operate throughout here, providing an affordable way for you to navigate the region without hassle.
  • Ride-Sharing Services: Popular services like Uber and Lyft are readily available, offering flexible and quick transportation directly from your vacation rental in the area.

Local Customs Options

  • Community Festivals: Participating in local festivals is a cherished tradition here, offering you an authentic experience of the area's vibrant cultural heritage and community spirit.
  • Respect for Historical Sites: When exploring the region, remember to honor and preserve the historic landmarks that tell the story of this destination's rich past.
  • Food Etiquette: Enjoying regional cuisine involves embracing local dining customs, such as sharing meals with neighbors and supporting small businesses.
  • Public Transportation Norms: Navigating here often involves using public transit respectfully by following designated rules and being considerate of fellow travelers.

Frequently Asked Questions About East Side?

1. What are the top vacation rentals in East Side?

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

2. Which vacation homes in East Side are best for families?

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

3. How many Rentbyowner vacation rentals are available in East Side?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 271 in the East Side 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 East Side. 

4. What is the cancellation policy for vacation rentals in this area?

Cancellation policies can vary depending on the individual property owner. It is recommended to review the specific cancellation terms listed with each rental or contact the host directly for detailed information.

5. How do I ensure my booking in Chicago’s East Side is secure and reliable?

Booking through trusted listings that provide verified owner information and secure payment options helps ensure a safe and dependable reservation experience in this region.

6. Are there any additional fees or charges I should be aware of when booking here?

Additional fees such as cleaning, service charges, or local taxes may apply; these details are typically outlined in the listing description or during the booking process.

7. What amenities are usually included in vacation rentals in this region?

Most properties offer essential amenities like Wi-Fi, kitchen facilities, and laundry; however, it’s best to check each listing for specific features available during your stay.

8. Can I contact the property owner before finalizing my booking?

Yes, most listings provide a way to communicate with the owner or host directly to ask questions and confirm details before securing your reservation.