Discover Your Perfect North Side Vacation Homes

North Side Pet Friendly Vacation Rentals

7.8 (585 Reviews)
Bed & Breakfast
The Villa Toscana
  • Parking
  • Pet Friendly
  • Security/Safety
View Availability
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9.4 (202 Reviews)
Bed & Breakfast
Ray's Bucktown Bed and Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
See More Pet-Friendly Vacation Rentals in North Side on PetFriendly.io

North Side Large Vacation Homes

See More Family Vacation Rentals in North Side on FVR

Why Choose Rent By Owner for your North 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 North Side Vacation Rentals

Where are the best neighborhoods to stay in North Side?

Discover the vibrant neighborhoods of North Side, Illinois, where your ideal stay awaits. Whether you're seeking a lively atmosphere or a quiet retreat, this area offers a variety of options that cater to different preferences. By choosing your accommodations in North Side, you'll enjoy convenient access to local attractions and scenic views, making your visit both memorable and comfortable. Explore the diverse neighborhoods to find the perfect backdrop for your vacation experience in North Side, Illinois.

Downtown Chicago

Staying in the heart of the city offers easy access to vibrant entertainment, shopping, and cultural attractions that make this destination a lively hub for visitors. It’s an ideal choice for those wanting to experience the city's energy while having convenient accommodations nearby.

View 1791+ Rentals in Downtown Chicago

River North

Known for its stylish dining, galleries, and nightlife, this neighborhood provides an energetic atmosphere perfect for exploring the best of the region’s arts and entertainment scene. Choose here if you're seeking a dynamic area with plenty of trendy options within reach.

View 484+ Rentals in River North

Lincoln Park

Offering a serene environment with lush parks and proximity to the lake, this area is perfect for those wanting a peaceful retreat close to nature and outdoor activities. It's an excellent base for relaxed exploration while remaining near the city’s vibrant attractions.

View 143+ Rentals in Lincoln Park

Lakeview

Vibrant and diverse, this neighborhood is ideal if you appreciate lively streets, local events, and historic charm, all within easy reach of the region's popular venues. It’s a welcoming spot for travelers looking to immerse themselves in authentic city life.

View 236+ Rentals in Lakeview

Near North Side

This centrally located area combines urban sophistication with convenient access to shopping districts and lakeside parks, making it a desirable place for travelers who want to be close to everything. Staying here provides a perfect balance of comfort and accessibility.

View 818+ Rentals in Near North Side

Gold Coast

Renowned for its upscale atmosphere and historic architecture, this district appeals to visitors seeking luxurious surroundings while enjoying the city's finest restaurants and shops. It’s an ideal backdrop for a refined urban experience.

View 39+ Rentals in Gold Coast

Wrigleyville

Famous for its spirited sports culture, this neighborhood attracts visitors eager to catch a game or enjoy lively nightlife. It’s a great choice if you’re looking to stay in an area full of energy and local pride.

View 45+ Rentals in Wrigleyville

Boystown

Celebrated for its vibrant LGBTQ+ community and inclusive atmosphere, this neighborhood offers a welcoming environment with a variety of entertainment, dining, and cultural experiences. It’s perfect for travelers seeking a friendly, lively neighborhood to explore.

View 679+ Rentals in Boystown

Best Times to Visit North Side

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit here ensures you can enjoy the region’s best weather and local events, making your stay in this destination truly memorable and well-suited to your vacation plans.

Peak Season Highlights

summer
Summer (June to August)

During the peak summer months, the region experiences warm weather that is ideal for exploring outdoor activities and enjoying the local atmosphere. This is when you can expect higher demand for vacation rentals in North Side, Illinois.

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

The early fall months attract visitors with pleasant temperatures and vibrant foliage, making it a popular time to visit this destination. Expect increased availability and competitive rates for vacation rentals during these months.

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

Off-Season Highlights

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Winter (December to February)

In winter, colder temperatures and fewer tourists mean lower rates and more flexibility when booking vacation rentals here. It’s an ideal time for those seeking tranquility and budget-friendly options.

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

Spring brings milder weather and fewer visitors, offering a peaceful experience. Vacation rentals tend to be more available and attract those looking for a quiet getaway in the area.

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

Weekly Weather Forecast for North Side

How to Book Your North 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 North Side

More Top-Rated Vacation Rentals in North 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 grilling and dining areas for memorable family meals or gatherings with friends.
  • Relax in a private backyard space, perfect for unwinding after exploring the area’s attractions.
  • Take advantage of outdoor seating and lounge areas to soak up the sunshine and scenic views.
  • Benefit from well-maintained gardens or landscaped yards that enhance your outdoor experience.
  • Make use of dedicated parking spaces with easy access to the outdoor amenities.
  • Explore nearby parks or green spaces that may be accessible directly from your rental property.
  • Utilize outdoor recreational equipment such as bicycles, volleyball courts, or swimming pools when available.

Top Attractions Around North Side

What attractions are nearby?

In this vibrant region, you can enjoy a variety of outdoor recreational activities, cultural experiences, and local dining options just moments from your North Side accommodation.

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Family Activities

  • Lincoln Park Zoo: Spend a day exploring this renowned zoo, where you can observe a wide variety of animals and enjoy family-friendly exhibits right in the heart of the area.
  • Chicago Children's Museum: Engage your little ones with interactive exhibits and hands-on activities designed to entertain and educate within the nearby navy pier complex.
  • Navy Pier: Take a leisurely stroll along the waterfront, enjoying rides, boat cruises, and spectacular views that make for a memorable family outing.
  • Lake Michigan Beaches: Relax and play at the beautiful beaches along the shoreline, offering opportunities for swimming, picnicking, and building sandcastles with your loved ones.
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Adult Activities

  • Explore Lincoln Park Zoo: Spend a day discovering diverse animal exhibits at one of the most renowned free zoos in the country, right here in this area.
  • Visit the Peggy Notebaert Nature Museum: Immerse yourself in local ecosystems and enjoy interactive exhibits that highlight the natural beauty of the region.
  • Enjoy a walk along Lake Michigan: Experience scenic views and refreshing breezes by strolling along the waterfront, a favorite activity for visitors seeking relaxation in this part of the city.
  • Discover the Chicago History Museum: Dive into the area's rich past and cultural heritage through engaging exhibits conveniently located nearby.

Other Places to Stay in North Side, IL

Lakeview
Lakeview Vacation Rentals
Lincoln Park
Lincoln Park Vacation Rentals
Logan Square
Logan Square Vacation Rentals
Lake View East
Lake View East Vacation Rentals
Old Town
Old Town Vacation Rentals
Old Town Triangle
Old Town Triangle Vacation Rentals
North Center
North Center Vacation Rentals
Wrigleyville
Wrigleyville Vacation Rentals
Avondale
Avondale Vacation Rentals
Sheffield and DePaul
Sheffield and DePaul Vacation Rentals
West Bucktown
West Bucktown Vacation Rentals
Park West
Park West Vacation Rentals
More Places to Stay Near North Side

North Side Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Transportation: Arranging your transportation options in advance ensures smooth travel throughout the area, allowing you to explore North Side's highlights comfortably.
  • Explore Local Dining Options: Take advantage of the region's diverse culinary scene by researching recommended eateries near your vacation rental for authentic dining experiences.
  • Check for Nearby Attractions: Familiarize yourself with nearby attractions and activities to maximize your time here and enrich your stay in this lively destination.
  • Book Early for Popular Rentals: Secure your ideal vacation rental early to guarantee availability during peak seasons and enjoy a stress-free booking process in this sought-after area.

Transportation Options

  • Chicago O'Hare International Airport: This major airport offers convenient domestic and international flights, making it easy for you to reach the region quickly.
  • Public Transit - CTA Blue Line: This subway connection provides direct access from here to downtown Chicago and surrounding neighborhoods, ideal for exploring the area without a car.
  • Metra Rail Service: Commuter trains connect the region to various parts of Illinois, offering a reliable transportation option for day trips or commuting.
  • Local Bus Services: The area's extensive bus network ensures smooth and affordable travel throughout North Side and nearby destinations.

Local Customs Options

  • Respect for Local History: When visiting here, it's customary to honor the area's rich history by participating in community events and respecting historical sites.
  • Local Cuisine Etiquette: Embracing regional culinary traditions involves trying local dishes with appreciation and understanding of their cultural significance.
  • Community Engagement: Engaging with residents through neighborhood gatherings and local markets is a valued custom that enhances your experience in this destination.
  • Environmental Respect: Practicing eco-friendly habits, such as proper waste disposal and conservation efforts, aligns with the community’s commitment to sustainability here.

Frequently Asked Questions About North Side?

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

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

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

There are 2 vacation rentals with private pools near North Side. Top-rated RBO homes that have access to a swimming pool include:

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

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

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 1028 in the North 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 North Side. 

5. What is the cancellation policy for vacation rentals in North Side, Illinois?

The cancellation policy varies depending on the individual property listing. You should review the specific terms outlined by the host before booking, or contact them directly for detailed information.

6. Are there any additional fees I should be aware of when booking a vacation rental in this area?

Additional fees such as cleaning fees, service charges, or security deposits are common and will be detailed in the listing. It's best to read the full description or reach out to the owner for clarification.

7. How do I find a pet-friendly vacation rental in North Side, Illinois?

Many listings specify whether they allow pets. Use the search filters to narrow down your options to pet-friendly properties, and check the listing details for any specific requirements or restrictions.

8. What amenities are typically included in vacation rentals around this destination?

Amenities vary by property but often include Wi-Fi, kitchen facilities, parking, and laundry services. For exact features, refer to the property’s detailed listing or contact the host directly.

9. How can I modify or cancel my reservation in North Side, Illinois?

Modification and cancellation policies depend on the specific listing. Review the terms provided in your booking confirmation or contact the property owner to discuss any changes or cancellations.