Discover Your Perfect West Side Vacation Homes

West Side Large Vacation Homes

See More Family Vacation Rentals in West Side on FVR

Why Choose Rent By Owner for your West 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.

Popular Areas for West Side Vacation Rentals

Where are the best neighborhoods to stay in West Side?

When exploring the West Side of Illinois, you’ll find a variety of neighborhoods that offer unique charm and easy access to local attractions. Each area provides a different atmosphere, making it simple to find the perfect place to stay during your visit. Whether you're seeking a lively neighborhood with vibrant culture or a quieter spot for relaxation, the West Side’s diverse communities cater to all preferences. Booking your ideal vacation rental in this region ensures an authentic experience, complemented by the convenience and reliability you expect from a trusted platform.

Downtown Chicago

In this vibrant part of the city, you’ll find a lively urban atmosphere with easy access to the region’s best dining, shopping, and entertainment options. Staying here places you right in the heart of the action, making it ideal for exploring the city's dynamic culture.

View 1791+ Rentals in Downtown Chicago

The Loop

This central area is perfect for those who want to experience the city's iconic skyline and bustling business district. Your stay here offers convenient proximity to major attractions and a lively downtown vibe that captures the essence of the region.

View 775+ Rentals in The Loop

River North

Known for its vibrant arts scene and trendy nightlife, this neighborhood is an excellent choice for travelers seeking stylish accommodations close to cultural hotspots. Staying here allows you to immerse yourself in the region’s creative energy and sophisticated eateries.

View 484+ Rentals in River North

Lincoln Park

Offering a more relaxed atmosphere, this neighborhood combines beautiful park views with charming boutiques and cafes. It’s an ideal spot to enjoy the region's natural beauty while remaining within reach of the city’s main attractions.

View 143+ Rentals in Lincoln Park

West Loop

Renowned for its innovative culinary scene and modern loft-style accommodations, this area appeals to travelers looking for trendy, upscale lodging options. Staying here provides a convenient base to explore the region’s thriving food culture.

View 198+ Rentals in West Loop

Near North Side

This upscale neighborhood offers a blend of luxury and accessibility, with high-end dining, shopping, and waterfront views. It’s a prime choice for visitors wanting to experience the region’s sophisticated side.

View 818+ Rentals in Near North Side

Wicker Park

Famous for its hipster vibe and eclectic storefronts, this neighborhood draws those wanting to enjoy arts, music, and unique local cafes. Staying here puts you in the midst of a creative community within the regional hub.

View 40+ Rentals in Wicker Park

Logan Square

Known for its lively street festivals and diverse culinary options, this area offers a more laid-back yet culturally rich experience. It’s an excellent destination for travelers seeking an authentic taste of the local scene.

View 78+ Rentals in Logan Square

Best Times to Visit West Side

When should you plan your Vacation Rentals stay?

Choosing the right time to visit this destination ensures you can enjoy its local charm and outdoor activities at their best, making your stay in the region truly memorable.

Peak Season Highlights

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Summer (June to August)

During the summer months, this destination experiences its peak season as visitors flock here to enjoy warm weather and outdoor activities. Booking your vacation rentals early ensures you secure the best options in the region.

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

Autumn draws many travelers looking to experience the vibrant foliage and pleasant climate. Securing your accommodations during this time provides a comfortable stay amid scenic surroundings in the area.

Average Temperature Daytime: around 75°F - Nighttime: around 50°F

Off-Season Highlights

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Winter (December to February)

The cold winter months see fewer visitors, making it an ideal period for those seeking quieter getaways. You can often find better deals on vacation rentals during this off-peak time.

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

Early spring offers mild weather and fewer crowds, providing a peaceful setting for your stay. Planning ahead allows you to find cozy vacation rentals at more affordable rates.

Average Temperature Daytime: around 60°F - Nighttime: around 40°F

Weekly Weather Forecast for West Side

How to Book Your West 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 West Side

More Top-Rated Vacation Rentals in West 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 a private outdoor patio or deck perfect for relaxing after a day of exploring the area.
  • Take advantage of a well-maintained garden or yard, ideal for outdoor activities or family gatherings.
  • Relax by an outdoor swimming pool, offering a refreshing escape during warm weather.
  • Utilize outdoor grilling facilities to prepare delicious meals alfresco with friends and family.
  • Make use of dedicated outdoor dining spaces that provide a scenic setting for your meals.
  • Benefit from access to nearby parks or green spaces for picnics, walking, or cycling adventures.
  • Experience the convenience of off-street parking amenities suited for vehicles of all sizes.

Top Attractions Around West Side

What attractions are nearby?

Within this vibrant region, you can enjoy a variety of outdoor activities, cultural experiences, and local attractions that offer a perfect blend of leisure and adventure during your stay.

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Family Activities

  • Lincoln Park Zoo: Spend a day exploring this free zoo, where you can enjoy close-up encounters with animals and engaging educational exhibits suitable for all ages.
  • Shedd Aquarium: Discover a fascinating underwater world at this renowned aquarium, offering interactive displays and family-friendly marine life shows in the region.
  • Maggie Daley Park: Enjoy outdoor adventures at this scenic park with climbing walls, playgrounds, and beautiful views of the city skyline designed for family fun.
  • The Field Museum: Dive into natural history at this famous museum, where your family can explore engaging exhibits on dinosaurs, ancient civilizations, and more right here in the area.
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Adult Activities

  • Explore the Chicago Riverwalk: You can enjoy a scenic stroll along the river, taking in stunning city views and vibrant local life right in this part of Illinois.
  • Visit the Art Institute of Chicago's nearby exhibits: This renowned cultural institution offers impressive collections that are easily accessible and showcase the region’s rich artistic heritage.
  • Relax at Millennium Park: An iconic urban park where you can unwind, admire unique public art installations, and experience the lively atmosphere just a short distance away.
  • Discover Navy Pier: A popular destination offering entertainment, dining, and scenic boat cruises, perfect for immersing yourself in the area's vibrant scene.

Other Places to Stay in West Side, IL

Near West Side
Near West Side Vacation Rentals
West Town
West Town Vacation Rentals
West Loop
West Loop Vacation Rentals
East Village
East Village Vacation Rentals
University Village / Little Italy
University Village / Little Italy Vacation Rentals
River West
River West Vacation Rentals
Lower West Side
Lower West Side Vacation Rentals
Wicker Park
Wicker Park Vacation Rentals
Pulaski Park
Pulaski Park Vacation Rentals
Noble Square
Noble Square Vacation Rentals
Tri-Taylor
Tri-Taylor Vacation Rentals
Heart of Chicago
Heart of Chicago Vacation Rentals
More Places to Stay Near West Side

West Side Travel Tips

How Can You Make the Most of Your Stay?

  • Research local attractions and dining options: Take some time to explore what the area offers so you can plan activities that make your stay memorable without missing out on hidden gems.
  • Choose a well-located vacation rental: Opt for properties close to key sites and transportation, ensuring easy access to everything this destination has to offer.
  • Plan your itinerary in advance: Organize your days around the region’s highlights to maximize your time and enjoy a diverse range of experiences during your visit.
  • Communicate with your host or property manager: Clarify any questions prior to arrival to ensure a smooth check-in and a comfortable stay at your chosen vacation rental here.

Transportation Options

  • Chicago Transit Authority (CTA): The CTA offers extensive bus and train services that make exploring the area convenient for visitors staying in this part of Illinois.
  • Metra Commuter Rail: Providing reliable rail connections to downtown Chicago and beyond, Metra is an efficient option for those looking to venture outside the region with ease.
  • Taxi and Rideshare Services: Local taxi companies and rideshare options like Uber and Lyft are readily available here, offering flexible transportation throughout the region.
  • Rental Car Services: Several rental agencies operate nearby, giving you the freedom to explore the area at your own pace from your vacation rental here.

Local Customs Options

  • Local Cuisine Appreciation: Engaging with the region’s culinary customs means sampling traditional dishes that reflect its rich cultural heritage, offering a genuine taste of your destination.
  • Respect for Community Events: Participating in or observing local festivals and parades provides an authentic connection to the area's vibrant traditions and social fabric.
  • Greeting Etiquette: Understanding customary greetings here ensures respectful interactions with residents and enhances your cultural experience during your stay.
  • Environmental Respect: Practicing eco-friendly habits aligns with the community's values, helping you enjoy your visit while preserving the area's natural beauty.

Frequently Asked Questions About West Side?

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

There are a lot of options in West Side. If you plan on staying in the West 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 West Side:

2. How many vacation rentals have private pools in West Side?

There are 7 vacation rentals with private pools near West Side. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in West Side are best for families?

If you are looking for a family-friendly vacation home in West 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 West Side:

4. How many Rentbyowner vacation rentals are available in West Side?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 1264 in the West 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 West Side. 

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

Cancellation policies vary by property, so it’s best to review the specific listing details and contact the owner directly to understand the terms that apply to your reservation.

6. Are there any specific requirements or restrictions when booking a vacation rental here?

Each property may have its own rules regarding minimum stay, guest limitations, or other requirements. Always check the property listing for detailed restrictions and communicate with the owner if you have special requests.

7. How do I ensure my booking is secure and reliable?

Bookings are handled through a trusted platform that offers secure payment options and verified listings. To guarantee your reservation’s safety, consider booking only through verified hosts and reading recent reviews.

8. What amenities are typically included in the vacation rentals in this region?

Most properties offer essential amenities such as Wi-Fi, parking, and kitchen facilities. However, each listing varies, so reviewing the amenities section on the property page will give you all the necessary details.

9. Is there a flexible check-in and check-out process available?

Flexible check-in and check-out times depend on the individual host’s policies. Contact the property owner ahead of time to discuss your arrival plans and confirm a suitable schedule.

West Side Top Rated Vacation Rentals

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