Old Town Triangle vacation rentals

We found 143 vacation rentals — enter your dates for availability

Discover a selection of 8 apartments and other vacation rentals in Old Town Triangle that are perfect for your trip. Vacation rentals provide the amenities you need and want for you and your friends, family, or even pets, such as air conditioning and a pool. You'll be sure to find a rental to meet everyone's needs, including places that are non-smoking or accessible.

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Find out more about Old Town Triangle

Why visit Old Town Triangle

  • Historic Charm: Explore the picturesque streets and beautifully preserved homes in the historic Old Town neighborhood.
  • Cultural Experiences: Immerse yourself in the vibrant community spirit and local culture of Old Town Triangle.
  • Family-Friendly Activities: Enjoy a variety of outdoor activities that cater to families and visitors of all ages.
  • Iconic Urban Parks: Relax and unwind in the urban parks that offer a perfect blend of nature and city life.
  • Diverse Accommodation Options: Choose from cozy apartments, spacious homes, and stylish condos for your stay.

Popular types of accommodation around Old Town Triangle

Looking for the perfect getaway in Old Town Triangle? You’re in the right place. Our most popular vacation rental options include cozy apartments, spacious private homes, and stylish condos. Whether you're searching for affordable Old Town Triangle apartments, charming homes for rent, or convenient bedroom rentals, we provide transparent listings to help you find the ideal spot for your stay. Enjoy your adventure with confidence and ease.

  • Apartments: The top choice for vacation rentals in Old Town Triangle, offering convenience and a home-like atmosphere for solo travelers or families.
  • Houses: A favored option for larger groups or families, providing spacious accommodations with all the comforts of home.
  • Condos: A popular selection for those seeking modern amenities and a vibrant community feel during their stay.
  • Cottages: These charming retreats provide a cozy escape, ideal for a romantic getaway or quiet weekend.
  • Villas: The perfect choice for luxury seekers wanting ample space and upscale amenities in a picturesque setting.**

Top attractions near Old Town Triangle

Old Town Triangle in Chicago is perfect for families and outdoor enthusiasts seeking a vibrant city experience. Visitors can explore iconic skyscrapers, relax in urban parks, and stroll through charming streets. This area offers a rich cultural experience while showcasing historical properties and the unique ambiance of the town triangle. Whether you're looking for family activities or cultural attractions, Old Town Triangle has something for everyone to enjoy.

  • Michigan Avenue: A bustling thoroughfare known for its vibrant atmosphere, Michigan Avenue is lined with iconic shops, restaurants, and stunning architecture, making it a prime destination for urban exploration.
  • Navy Pier: This famous jetty offers a blend of entertainment, scenic views of Lake Michigan, and friendly vibes. Enjoy attractions, dining, and beautiful sunsets while strolling along the waterfront.
  • Millennium Park: A family-friendly urban park featuring stunning art installations, lush gardens, and outdoor concerts, perfect for relaxation and enjoyment in the heart of the city.

Things to do recommended for couples

For a romantic getaway in Old Town Triangle, enjoy live music at the House of Blues, just 2 miles away. Savor a cozy dinner at the Historic Michael Jordan Restaurant, also 2 miles away, or experience the vibrant atmosphere of the Aragon Ballroom, located 4 miles away.

Things to do recommended for families

Families can catch a game at Wrigley Field, just 3 miles away, or unwind at the Northerly Island Natural Area, 4 miles from Old Town Triangle. For fitness enthusiasts, The East Bank Club, located 2 miles away, offers excellent recreational facilities for all ages.

Things to do recommended for groups

Groups visiting Old Town Triangle can enjoy a show at the historic Chicago Theatre, share laughs at Second City, and shop at Chicago Place Mall, all while soaking in the vibrant local culture and family-friendly atmosphere of this charming neighborhood.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Old Town Triangle

If you're traveling with a group, family, pets, or planning an extended stay, it's important to prioritize your search filters accordingly. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Old Town Triangle with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Old Town Triangle with young kids: Traveling with young kids can be quite a task. It's essential to prioritize their comfort and safety, along with amenities that are suitable for their age, like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Old Town Triangle: For many families, a vacation just isn't the same without their furry companions. If this resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly properties come equipped with feeding bowls and cozy beds, ensuring that every member of the family feels at home.
  • Planning for a long term stay visiting Old Town Triangle: If you're in search of vacation rentals that offer discounts for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Old Town Triangle

Old Town Triangle in Chicago offers a charming blend of family-friendly atmosphere and urban scenery, making it an ideal vacation spot. Explore the historic Old Town neighborhood, known for its beautiful family homes and vibrant community spirit. Enjoy outdoor activities and immerse yourself in the local culture while discovering friendly people and picturesque streets. With its unique character, Old Town Triangle is a delightful destination for travelers seeking a memorable experience in the heart of Chicago.

  • Chicago: As a bustling metropolis, Chicago is the heart of Old Town Triangle, offering a vibrant mix of family-friendly activities and urban exploration. Visitors can enjoy the city's renowned shopping areas, indulge in arena entertainment, and immerse themselves in educational experiences. Local landmarks include iconic stadiums and sports facilities, making it a perfect destination for sports enthusiasts and tourists alike. With its unique blend of cultural attractions and outdoor spaces, Chicago provides an unforgettable travel experience.
  • Downtown Chicago: Located 2 miles from Old Town Triangle, Downtown Chicago is a lively neighborhood that draws families and outdoor enthusiasts. The area is known for its impressive shopping districts, world-class theater venues, and entertainment options. Visitors can explore major attractions, including tourist precincts and sports stadiums, ensuring a holistic city-themed experience. Downtown Chicago's stunning architecture and vibrant atmosphere make it a must-visit while exploring the Windy City.
  • Magnificent Mile: Just 2 miles away from Old Town Triangle, Magnificent Mile is an iconic stretch known for its luxurious shopping, dining, and entertainment. This lively neighborhood attracts families and city explorers with its vibrant atmosphere. In addition to high-end retail and theater options, visitors can engage in educational experiences at nearby attractions. The area's proximity to major landmarks, including stadiums and sports facilities, ensures a dynamic experience filled with excitement and culture.

Best time to go to Old Town Triangle

If you're planning a trip to Old Town Triangle, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like December to February tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.7°F (-3.5°C)Light RainMostly CloudyModerately LowSlightly Low
February27.0°F (-2.8°C)Light RainMostly CloudyModerately LowSlightly Low
March37.0°F (2.8°C)Light RainMostly CloudyAverageSlightly Low
April46.0°F (7.8°C)Light RainMostly SunnyAverageAverage
May57.0°F (13.9°C)Light RainMostly SunnyAverageAverage
June67.3°F (19.6°C)Light RainMostly SunnyModerately HighSlightly High
July73.4°F (23.0°C)Light RainMostly SunnyModerately HighSlightly High
August73.0°F (22.8°C)Light RainMostly SunnyModerately HighSlightly High
September67.1°F (19.5°C)Light RainMostly SunnyAverageAverage
October54.9°F (12.7°C)Light RainMostly SunnyAverageAverage
November42.3°F (5.7°C)Light RainMostly SunnyAverageAverage
December33.1°F (0.6°C)Light RainMostly CloudyModerately LowAverage

Booking with Vrbo is simple

Are you aiming to save money on your upcoming trip? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking a longer stay to take advantage of substantial savings. To discover a Vrbo property that meets your budget, simply use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your booking. Being the planner has its perks. When you enroll in our travel rewards program, One Key, you’ll gain immediate access to exclusive member savings and can earn and redeem OneKeyCash on eligible reservations. Sign up today to begin enjoying the benefits.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a convenient way to plan your travel. You can easily create new trips, pick up right where you left off, or organize your upcoming plans. All the properties you've saved and booked are now neatly categorized under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Old Town Triangle?
In Old Town Triangle, apartments are the most popular type of vacation rental, with about 13 available throughout the neighborhood. These apartments are typically situated in charming buildings, featuring amenities like fully equipped kitchens, cozy living areas, and some even have access to private balconies for enjoying the vibrant surroundings. Additionally, there are around 10 vacation houses that provide more space, ideal for families or larger groups. These homes often come with multiple bedrooms, outdoor areas, and amenities such as BBQ grills, making them great for gatherings.
Are there any beach house rentals in Old Town Triangle?
In Old Town Triangle, Illinois, there are several beach house rentals available, primarily situated near the scenic shores of Lake Michigan. These properties typically feature charming architectural styles that reflect the historic nature of the neighborhood, offering a mix of modern amenities and classic details. Travelers can expect vacation homes with multiple bedrooms, spacious living areas, fully equipped kitchens, and outdoor spaces for enjoying the beautiful lake views.
How much does it cost to rent a vacation home in Old Town Triangle?
Prices for vacation rentals in Old Town Triangle 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 Old Town Triangle 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 Old Town Triangle vacation house rentals?
You can find great discounts on house rentals in Old Town Triangle 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.
What are popular rental amenities in Old Town Triangle?
In Old Town Triangle, travelers can expect a variety of vacation rental amenities that enhance their stay. Most rentals typically feature a fully equipped kitchen, superb for preparing meals during your visit. Many rooms also include a coffee and tea maker for a warm beverage in the morning, as well as a kitchen island that provides additional prep space and a casual dining area. Outdoor spaces are common, with patios available for enjoying the fresh air and city views. Additionally, many rentals come equipped with convenient appliances like blenders, making it easy to whip up smoothies or other blended beverages.
Are there any family house rentals in Old Town Triangle?
In Old Town Triangle, Illinois, there is a great selection of family-friendly house rentals, with around 17 options available. This historic neighborhood is known for its charming architecture and vibrant atmosphere, making it an ideal spot for families to stay. Many of these homes come equipped with spacious living areas, fully stocked kitchens, and outdoor spaces where children can enjoy themselves. Visitors can often find amenities like laundry facilities, Wi-Fi, and comfortable furnishings to make their stay even more enjoyable.

The locale is conveniently located near popular attractions such as the Lincoln Park Zoo and the beautiful Lincoln Park Conservatory, both of which are great for family outings. Additionally, families can explore nearby parks and playgrounds, ensuring plenty of opportunities for outdoor fun.
Can I rent a vacation home with a pool or hot tub in Old Town Triangle?
In Old Town Triangle, Illinois, there are several vacation homes available for rent that feature pools and hot tubs. This historic neighborhood is known for its charming architecture and vibrant atmosphere, making it an appealing destination for travelers. Properties in this area often include amenities such as private pools, hot tubs, outdoor seating areas, and well-equipped kitchens, great for relaxation and entertaining.
Are there any Old Town Triangle vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Old Town Triangle with parking available—perfect for families or travelers 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.
Are there pet-friendly vacation rentals in Old Town Triangle?
Yes, you can book pet-friendly vacation rentals in Old Town Triangle, with around 17 options available. This charming neighborhood is known for its historic architecture and vibrant community atmosphere. Many of the vacation rentals here come equipped with modern amenities such as updated kitchens, spacious living areas, and outdoor spaces where your pets can enjoy some fresh air.

Old Town Triangle is close to several parks, including the picturesque Lincoln Park, which features walking trails, gardens, and even a zoo, making it an ideal spot for pet owners. The area is also dotted with pet-friendly cafes and boutiques, adding convenience and enjoyment for travelers with furry companions.
Can I find long-stay vacation rentals in Old Town Triangle?
A long-stay vacation rental in Old Town Triangle is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Old Town Triangle for a vacation rental?
July is the most popular time to visit Old Town Triangle, where the vibrant energy of summer captivates travelers seeking a blend of culture and outdoor exploration. This peak season, which runs from May through July, attracts visitors eager to experience the area's charming streets, historic architecture, and bustling art scene. With average temperatures hovering in the mid-70s to low 80s Fahrenheit, the warm weather creates an inclusive setting for leisurely strolls and outdoor dining.

During this lively period, you'll find an abundance of events and activities, including street festivals and art fairs, making it an ideal time for those looking to immerse themselves in local culture. The proximity to beautiful parks and the scenic Lake Michigan shoreline also adds to the appeal, offering ample opportunities for sightseeing and outdoor adventures.

If you're seeking a more budget-friendly option, consider visiting in December. This month, while quieter, presents a unique charm as Old Town Triangle transforms into a winter wonderland, superb for cozy walks and enjoying the festive holiday lights.
Are there any remote work vacation rentals in Old Town Triangle?
In Old Town Triangle, Illinois, there are numerous vacation rentals well-suited for remote work, with around 25 options available. This vibrant neighborhood is known for its historic charm, featuring beautiful architecture and tree-lined streets, making it a pleasant environment for those looking to balance work and leisure. Many of these rentals come equipped with essential remote work amenities, including dedicated office spaces, high-speed Wi-Fi, desks, ergonomic chairs, and even computer monitors for a comfortable and productive work setup.

The area also offers easy access to local cafes and restaurants, providing convenient spots for coffee breaks or meals. Moreover, the proximity to parks and cultural attractions, such as the nearby Lincoln Park and the famous Second City theater, ensures that you can enjoy a variety of activities during your downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Old Town Triangle vacation rental?
Book your Old Town Triangle vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Old Town Triangle?
In Old Town Triangle, visitors can appreciate the charming historic architecture and vibrant atmosphere of the neighborhood. The area is known for its beautiful Victorian homes and tree-lined streets, making it a picturesque spot for a leisurely stroll. The Old Town Art Fair, held annually, showcases local artists and craftspeople, drawing in visitors from all over.

Nearby, Lincoln Park offers access to attractions like the Lincoln Park Zoo and the Lincoln Park Conservatory, which are great for enjoying nature and wildlife. The neighborhood also boasts a variety of dining options, from cozy cafes to upscale restaurants, reflecting the diverse culinary scene of Chicago. Furthermore, the proximity to the lakefront provides opportunities for outdoor activities, including biking and walking along the scenic paths.
Can I change or cancel my Old Town Triangle home rental booking on Vrbo?
To find Old Town Triangle vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 Old Town Triangle vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, 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 organizing 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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