Near North Side holiday lettings

We found 1,126 holiday rentals — enter your dates for availability

Discover a selection of 453 apartments, 29 flats and other holiday rentals in Near North Side that are perfect for your trip. Holiday rentals provide the best amenities for your stay with friends, family or just your pet, such as Wi-Fi and a pool. You'll be able to choose a property to rent for everyone's needs, including options that are accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

How much does it cost to rent a holiday home in Near North Side?
Prices for holiday rentals in Near North Side vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Near North Side to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Near North Side holiday house rentals?
You can find great discounts on house rentals in Near North Side on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Are there any Near North Side holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Near North Side with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I find long-stay holiday rentals in Near North Side?
A long-stay holiday rental in Near North Side is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Near North Side for a holiday rental?
The most popular time to visit Near North Side is from February to April, coinciding with the vibrant energy of spring. This peak season attracts a diverse range of travellers eager to enjoy the city's culture, art, and culinary delights. As the weather warms up, temperatures typically range from about 1 to 15 degrees Celsius, providing a comfortable climate for outdoor activities and sightseeing.

March, in particular, stands out as a highlight, with events like St. Patrick's Day parades and various festivals that add to the lively option. Visitors can easily explore the area's iconic attractions, such as the Magnificent Mile, Millennium Park, and the renowned Art Institute of Chicago, all while enjoying the blossoming scenery.

For those looking for a more budget-friendly option, November offers a quieter experience with fewer tourists. This month allows you to enjoy the city's charm without the crowds, making it an excellent time for leisurely strolls through local parks or exploring neighbourhood cafes.

Ultimately, the best time to book a holiday rental in Near North Side depends on your preference for vibrant events and social experiences in peak season or the tranquil enjoyment of the city in the shoulder months.
How early should I book a Near North Side holiday rental?
Book your Near North Side holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Near North Side, Illinois, United States of America?
In Near North Side, Chicago, visitors can enjoy a range of attractions that highlight the area's vibrant culture and rich history. The Magnificent Mile is a major draw, offering an array of high-end shops, restaurants, and iconic landmarks like the John Hancock Centre, where guests can take in stunning views from the observation deck.

The area is also home to Navy Pier, a popular entertainment destination featuring rides, dining options, and beautiful views of Lake Michigan. For those interested in art and culture, the Museum of Contemporary Art is located nearby, showcasing an impressive collection of modern art and hosting various exhibitions and events.

Additionally, the historic Old Town neighbourhood, just a short walk away, is famous for its charming architecture, lively option, and attractions like the Old Town Triangle Historic District, providing a glimpse into Chicago's past.
Can I change or cancel my Near North Side home rental booking on Vrbo?
To find Near North Side holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Near North Side holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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