Near East Side holiday rentals
We found 820 holiday rentals — enter your dates for availability
Discover a selection of 10 apartments and other holiday rentals in Near East Side that are perfect for your trip. Holiday homes offer the amenities that you expect for your stay with friends, family or just your pet, such as parking and a TV. No matter what you're looking for, you're sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.
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Find the best place to stay - Near East Side

Kasa Lake Shore Chicago
Sleeps 4 · 1 bedroom · 1 bathroom

Kasa Magnificent Mile Chicago
Sleeps 2 · 1 bedroom · 1 bathroom

Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
Sleeps 18 · 4 bedrooms · 4 bathrooms

Gold Coast Gem
Sleeps 6 · 2 bedrooms · 2 bathrooms

Kasa River North Chicago
Sleeps 3 · 1 bedroom · 1 bathroom

Kasa South Loop Chicago
Sleeps 6 · 3 bedrooms · 2 bathrooms
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of holiday rental in Near East Side?
In Near East Side, apartments are the most popular type of holiday rental, with several available throughout the area. These apartments are typically situated in vibrant neighbourhoods, offering easy access to local attractions and amenities. Most units come equipped with fully fitted kitchens, comfortable living areas, and modern furnishings, providing a homely atmosphere for guests. Additionally, some may feature communal facilities such as fitness centres or rooftop terraces, allowing visitors to enjoy the city views.
What are popular rental amenities in Near East Side?
In the Near East Side of Illinois, popular rental amenities include sofa beds, balconies, coffee and tea makers, and outdoor decks or patios, which enhance the comfort and convenience of stays. Many properties also feature fitness facilities, allowing guests to maintain their exercise routines while enjoying their holiday.
Can I find family house rentals in Near East Side?
In the Near East Side of Illinois, there are several family-friendly house rentals available, making it a great option for those travelling with children. This area offers a variety of spacious homes that typically feature multiple bedrooms, large living areas, and fully equipped kitchens, superb for preparing family meals. Many properties also boast outdoor spaces such as gardens or patios where kids can play and families can relax.Visitors will find themselves in proximity to nearby attractions, including parks and cultural sites, which provide plenty of opportunities for family outings. The local neighbourhood is known for its community vibe, ensuring that families will have a comfortable and enjoyable stay.
Can I rent a holiday home with a pool or hot tub in Near East Side?
In the Near East Side of Illinois, there are several holiday homes available for rent that feature pools and hot tubs. This vibrant area offers a mix of urban excitement and accessibility to local attractions. Travellers can expect a variety of amenities in these properties, such as private pools, relaxing hot tubs, spacious outdoor areas for gatherings, and fully equipped kitchens for self-catering. Many rentals also include modern conveniences like Wi-Fi and air conditioning, ensuring a comfortable stay.
Can I book pet-friendly holiday rentals in Near East Side?
In the Near East Side of Illinois, there are several pet-friendly holiday rentals available for those looking to explore the area with their furry companions. This vibrant neighbourhood offers a mix of modern amenities and easy access to various attractions. Many of the holiday rentals feature essential comforts such as fully equipped kitchens, spacious living areas, and laundry facilities, making them suitable for both short and extended stays.The Near East Side is close to several parks, providing ample opportunities for outdoor activities with pets. Notably, the expansive Grant Park is just a short distance away, where visitors can enjoy walking paths, gardens, and open spaces superb for leisurely strolls with dogs. Additionally, the area boasts pet-friendly cafes and shops, ideal for travellers with pets.
When is the best time to visit Near East Side for a holiday rental?
July is the most popular time to visit the Near East Side of Illinois, where vibrant city life meets a rich cultural tapestry. The peak season spans from May to July, superb for travellers eager to explore the area's attractions, including museums, parks, and lively street festivals. Expect a bustling atmosphere as visitors flock to enjoy the warm summer weather and take part in outdoor activities.Temperatures in July can reach a comfortable 25 to 30 degrees Celsius, ideal for sightseeing and leisurely strolls along the waterfront. With plenty of cafes and shops nearby, you can easily blend relaxation with exploration. The city's outdoor spaces, such as Grant Park and the Chicago Riverwalk, offer fantastic opportunities for picnics and people-watching.For those looking for a more budget-friendly option, consider visiting in December. This month, while cooler with temperatures averaging around 0 to 5 degrees Celsius, brings a unique charm as the city transforms into a winter wonderland with festive decorations and holiday markets. It's a quieter time, allowing for a more intimate experience of the city's offerings without the summer crowds.
Are there any remote work holiday rentals in Near East Side?
In the Near East Side of Illinois, there are several remote work-friendly holiday rentals available. These accommodations often cater to the needs of professionals seeking a comfortable working environment away from home. Many properties are equipped with high-speed internet, dedicated office spaces, and desks, ensuring that guests can maintain productivity during their stay.The area is conveniently located near various points of interest, including parks and local eateries, providing opportunities for relaxation and leisure after work hours. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are the top attractions in Near East Side, Illinois, United States of America?
In the Near East Side of Chicago, visitors can explore several popular attractions that highlight the city's rich culture and history. The Museum Campus is a prominent area, home to the Field Museum, the Shedd Aquarium, and the Adler Planetarium, all of which offer fascinating exhibits and experiences for all ages. Just a short stroll away, Grant Park provides expansive green spaces great for leisurely walks and picnics, along with iconic landmarks such as Buckingham Fountain.Additionally, the historic Chicago Women's Park and Gardens offers a serene retreat with beautiful landscapes and educational exhibits. The area also boasts convenient access to the vibrant South Loop neighbourhood, where visitors can find a variety of dining options and shopping venues, as well as cultural institutions like the Chicago Symphony Orchestra and the Art Institute of Chicago, located nearby.
Are all fees included in the Near East Side holiday homes prices shown on Stayz?
Stayz 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.
Are there any Near East Side holiday homes with parking?
Stayz offers a wide selection of holiday homes in Near East 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 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.
Are there any discounts for Near East Side holiday homes?
You can find great discounts on holiday homes in Near East Side on Stayz, 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.
Can I change or cancel my Near East Side holiday home booking on Stayz?
To find Near East Side holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Near East Side?
A long-stay holiday home in Near East 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Near East Side holiday home?
Book your Near East Side holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Near East Side?
Prices for holiday homes in Near East 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Near East Side to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
