Old Town Triangle vacation rentals

We found 138 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: Experience the rich history and architectural beauty of Old Town Triangle.
  • Family-friendly atmosphere: Enjoy a welcoming environment that caters to visitors of all ages.
  • Scenic outdoor spaces: Stroll through picturesque streets and urban parks, perfect for relaxation and exploration.
  • Diverse vacation rentals: Choose from cozy apartments to spacious homes for a comfortable stay.
  • Local culture: Immerse yourself in the vibrant community and friendly ambiance of Old Town Triangle.

Popular types of accommodation around Old Town Triangle

Discover the charm of Old Town Triangle with our diverse selection of vacation rentals. Whether you're looking for cozy apartments, spacious houses, or modern condos, we have the perfect option for you. Explore our listings for old town triangle houses and homes for rent, ensuring a comfortable stay tailored to your needs. With various bedroom configurations available, finding your ideal Old Town Triangle vacation rental has never been easier.

  • Apartments: The top choice for visitors in Old Town Triangle, offering convenient amenities and a home-like atmosphere.
  • Houses: Ideal for families or groups, these spacious homes provide a unique and comfortable experience.
  • Condos: A popular option, condos blend luxury with practicality, perfect for a stylish stay.
  • Cottages: Charming and cozy, cottages are great for a quaint getaway in a picturesque setting.
  • Villas: Offering elegance and space, villas are perfect for those seeking a lavish retreat.**

Top attractions near Old Town Triangle

Old Town Triangle in Chicago is perfect for family-friendly, outdoor city vacations. Visitors can explore iconic skyscrapers, urban parks, and charming streets, making it an ideal destination for culture and family experiences. Don't miss the opportunity to discover local rentals by neighborhood for a more immersive stay. This vibrant area offers a unique blend of attractions that cater to all types of travelers.

  • Michigan Avenue: Known as the Magnificent Mile, this vibrant street is famous for its upscale shopping, dining, and stunning architecture, offering a true city vibe that embodies the hustle and bustle of Chicago.
  • Navy Pier: A lively waterfront destination featuring attractions, restaurants, and scenic views of Lake Michigan, making it perfect for leisurely strolls and enjoying urban vibes with friendly locals.
  • Millennium Park: A family-friendly urban park that hosts art installations, concerts, and beautiful gardens, providing a refreshing outdoor experience in the heart of the city.

Things to do recommended for couples

Old Town Triangle offers a charming escape for couples. Enjoy a leisurely stroll through picturesque streets, visit cozy cafes, and explore the local art scene. Don't miss the enchanting Lincoln Park Rose Garden, perfect for a romantic picnic, and wrap up your day with a sunset walk along the lakefront.

Things to do recommended for families

Families will love exploring the Lincoln Park Zoo, home to diverse animals and free admission, or enjoying a fun day at the nearby Peggy Notebaert Nature Museum, which features interactive exhibits and a butterfly sanctuary for all ages.

Things to do recommended for groups

Groups visiting Old Town Triangle can enjoy a guided architecture tour of the historic district, savor delicious meals at local eateries, and participate in art workshops to experience the vibrant community culture. Don’t miss the chance to explore the nearby Lincoln Park and its beautiful zoo.

*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

When you're planning a trip—whether with a group, your family, or pets, or if you're seeking extended stays—be sure to refine your search based on your key priorities. Here are some helpful Vrbo booking tips to consider.

  • Traveling to Old Town Triangle with a group: Think about how many bedrooms you'll require, along with additional features like a full kitchen or outdoor space 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 children can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities 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 wouldn’t be the same without their furry companions. If you can relate, explore Vrbo listings that are pet-friendly. Most of these properties offer amenities like food bowls and pet beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Old Town Triangle: If you're searching for vacation rentals that offer discounts for stays of a month or more, 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 features 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 delightful blend of historic charm and vibrant urban life. This family-friendly neighborhood is perfect for outdoor enthusiasts and city explorers alike. Visitors can stroll through the picturesque streets of Old Town, soak in the scenic beauty, and experience the warm atmosphere created by friendly locals. With its rich history and welcoming ambiance, Old Town Triangle is an ideal destination for a memorable vacation.

  • Chicago: As a bustling metropolis, Chicago offers a vibrant urban experience that draws visitors from around the globe. Old Town Triangle is nestled within this dynamic city, making it an ideal base for your adventures. Explore the extensive shopping areas, catch a thrilling game at the sports facilities, or enjoy a show at one of the many theaters. Chicago's urban parks provide a refreshing contrast to the cityscape, perfect for family outings or leisurely strolls. Key attractions like Millennium Park and the iconic Willis Tower are within easy reach, ensuring your trip is filled with both excitement and relaxation.
  • Downtown Chicago: Located just 2 miles from Old Town Triangle, Downtown Chicago is the city's lively epicenter. This neighborhood is renowned for its family-friendly activities and outdoor spaces, making it a great spot for visitors of all ages. Enjoy world-class shopping, catch a performance at a local theater, or indulge in arena entertainment. The area is home to significant landmarks such as Grant Park and the Chicago Riverwalk, where you can unwind while soaking in stunning city views. Downtown Chicago effortlessly blends urban charm with entertainment options, ensuring a memorable travel experience.
  • Old Town Chicago: Mere 0.2 miles from Old Town Triangle, Old Town Chicago is a charming neighborhood that embodies the city's historic character. Known for its family-oriented atmosphere, this area is perfect for a day of exploration. Enjoy a variety of shopping venues and immerse yourself in the local theater scene. Outdoor spaces like Lincoln Park provide ample opportunities for relaxation and recreation. The neighborhood's proximity to attractions such as the Old Town Art Fair and the historic district adds to its appeal, ensuring that your visit is filled with cultural and recreational delights.

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 January to March 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 CloudyModerately LowSlightly 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 CloudyAverageAverage

Booking with Vrbo is a breeze

Are you aiming to save on your upcoming journey? Being open to different travel dates can help, as prices can vary. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the best options for your needs.

Vrbo Trips: Planning made easy

Vrbo's Trip Board offers a user-friendly platform for you to plan new trips, resume your previous arrangements, or manage your travel plans with ease. You can easily access your saved or booked properties, which are neatly organized into categories like Potential, Upcoming, or Current Trips. To begin utilizing 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 common vacation rental option, with around 12 available in this charming neighborhood known for its historic architecture and vibrant setting. These apartments typically feature fully equipped kitchens, cozy living spaces, and some may have balconies or patios offering views of the surrounding area. Additionally, several vacation houses and condos can be found, providing extra space for families or larger groups. These properties often come with amenities like outdoor seating areas, making them suitable for gatherings after exploring local attractions such as the nearby parks and cultural venues.
Are there any beach house rentals in Old Town Triangle?
In Old Town Triangle, there are several beach house rentals available, providing a unique stay in this historic neighborhood of Chicago. These vacation homes often boast amenities like fully equipped kitchens, spacious living areas, and outdoor patios or balconies for enjoying the vibrant surroundings. Being close to attractions such as the Lincoln Park Zoo, the Chicago History Museum, and the picturesque North Avenue Beach, these rentals offer a convenient base for exploring the city's cultural and recreational offerings.
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, vacation rentals often come equipped with a variety of popular amenities that enhance the guest experience. Most properties feature fully equipped kitchens, allowing travelers to prepare their own meals and enjoy dining in comfort. Additionally, many rentals include coffee and tea makers for a cozy start to the day. Onsite parking is a common amenity, providing convenience for those traveling with vehicles. Many homes also boast decks or patios, great for relaxing outdoors and enjoying the neighborhood's charm. A fireplace is another inviting feature found in several rentals, creating a warm and welcoming atmosphere, especially during the cooler months.
Can I find family house rentals in Old Town Triangle?
In Old Town Triangle, Illinois, there are several family-friendly house rentals available, with around 14 options to choose from. This charming neighborhood is known for its historic architecture and vibrant setting, making it a wonderful place for families to stay. Many of these homes feature spacious living areas, fully equipped kitchens, and outdoor spaces where children can play. Visitors can also expect amenities like Wi-Fi and air conditioning, ensuring a comfortable environment for everyone.

Additionally, the area is close to various attractions, including parks and cultural sites, providing opportunities for family outings and exploration.
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 both pools and hot tubs. This historic neighborhood is known for its charming architecture and vibrant setting, making it a desirable location for travelers. Many of these rentals come equipped with inviting outdoor spaces, superb for relaxation after a day of exploring the local attractions. Expect amenities such as fully equipped kitchens, spacious living areas, and outdoor seating areas that enhance the overall experience.
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.
Can I book pet-friendly vacation rentals in Old Town Triangle?
In Old Town Triangle, travelers can find a variety of pet-friendly vacation rentals, with around 11 options available to choose from. The neighborhood is known for its charming historic architecture and vibrant setting, making it an appealing destination for those traveling with pets. Many properties in this area come equipped with amenities such as modern kitchens, spacious living areas, and outdoor spaces where pets can enjoy some fresh air.

Old Town Triangle is conveniently located near several parks, including the nearby Lincoln Park, which features walking trails, gardens, and open spaces great for strolls with pets. Additionally, the area is home to pet-friendly cafes and shops, enhancing the overall experience 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?
The peak season for visiting Old Town Triangle falls between May and July, with July being the most popular month. During this vibrant period, the neighborhood comes alive with outdoor festivals, art fairs, and a bustling atmosphere that captivates both locals and travelers alike. The warm summer temperatures, often reaching the high 70s to low 80s Fahrenheit, create an inviting environment for leisurely strolls through the streets, exploring charming boutiques, and dining at al fresco restaurants.

For those who appreciate cultural experiences, this season offers an abundance of events, including art walks and performances that showcase the local talent. Whether you're interested in visiting the historic architecture or enjoying the diverse culinary scene, you'll find plenty of options to keep you entertained.

If you're looking for a more budget-friendly time to visit, consider planning your trip in December. This month brings a quieter charm to Old Town Triangle, with festive decorations and holiday markets that create a cozy atmosphere. You can enjoy the area's unique shops and galleries without the crowds, making it an excellent time for a more intimate experience.

Ultimately, your choice of when to visit Old Town Triangle will depend on whether you prefer the lively, energetic vibe of the summer months or the serene, festive spirit of the winter season.
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, Illinois, United States of America?
In Old Town Triangle, visitors can enjoy a unique blend of historic charm and vibrant culture. The neighborhood is known for its beautifully preserved Victorian architecture, providing a picturesque backdrop for leisurely strolls. One of the top attractions is the Old Town Triangle Historic District itself, which features quaint streets lined with local boutiques, art galleries, and cozy cafes.

Nearby, Lincoln Park offers a wealth of outdoor activities, including walking paths, playgrounds, and the Lincoln Park Zoo, which is free to the public and ideal for families. The area is also close to the Chicago History Museum, where visitors can explore the city's rich past through engaging exhibits. For those interested in the arts, the Old Town Art Fair, held annually, showcases local artists and craftspeople, making it a vibrant community event.
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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