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Woodlawn vacation rentals

We found 83 vacation rentals — enter your dates for availability

Discover a selection of 7 homes and other vacation rentals in Woodlawn that are perfect for your trip. Vacation rentals offer the amenities you expect for your stay with friends, family, or just your pet, such as parking and a pool. You're sure to find a rental for everyone's needs, including places that are non-smoking or accessible.

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Find out more about Woodlawn

Why visit Woodlawn

  • Rich Cultural Experiences: Woodlawn boasts a vibrant blend of family-friendly activities and cultural attractions, perfect for tourists.
  • Historic Charm: Discover the neighborhood's rich history through its historic houses and charming residential streets.
  • Urban Parks: Enjoy leisurely afternoons at local parks, ideal for picnics and outdoor activities.
  • Proximity to Beaches: Take advantage of nearby beaches for a refreshing escape from city life.
  • Diverse Accommodations: Find a range of vacation rentals, from cozy homes to stylish apartments, tailored for every traveler.

Popular types of accommodation around Woodlawn

Vrbo offers a variety of vacation rentals in Woodlawn, perfect for every traveler. Whether you're looking for stylish West Woodlawn apartments, spacious bedroom apartments, or cozy houses, we have options to suit your needs. Our selection also includes Riverdale apartments and vacation condos. Explore the best rental properties in Woodlawn for a memorable stay, tailored just for you.

  • Apartments: The most sought-after choice for staying in Woodlawn, offering a comfortable living space and essential amenities for travelers.
  • Houses: Ideal for families or groups, these homes provide a home-like atmosphere with privacy and space.
  • Condos: A popular option featuring modern conveniences and often located in vibrant areas of Woodlawn.
  • Cottages: Charming and cozy, these rentals offer a quaint and relaxing getaway experience.
  • Villas: Luxurious accommodations that provide upscale amenities and spacious environments for a lavish stay.**

Top attractions near Woodlawn

Woodlawn, Chicago, offers a delightful blend of family-friendly and cultural experiences perfect for outdoor vacations. Visitors can explore urban parks, historic houses, and nearby beaches, making it an ideal destination for those seeking a vibrant city experience with a touch of history. Whether you're traveling with family or friends, Woodlawn has a variety of attractions to ensure a memorable getaway.

  • McCormick Place: A premier event venue known for its impressive size and modern facilities, McCormick Place hosts major conferences and conventions. Its business atmosphere makes it a hub for networking and innovation, located 5 miles from Woodlawn.
  • University of Chicago: This historic university features stunning Gothic architecture and a rich academic culture. Walking its campus, located 0.9 miles away, immerses you in an environment of intellectual curiosity and artistic expression.
  • Chicago Museum of Science and Industry: A family-friendly destination, this museum offers interactive exhibits that engage visitors of all ages. Located 2 miles away, it's a place where science meets fun, showcasing a wide array of fascinating topics.

Things to do recommended for couples

Looking for a romantic getaway in Woodlawn? Enjoy live music at the House of Blues, dine at the charming Grand Terrace Ballroom, or catch a show at Lincoln Hall. Each spot offers a unique vibe to create unforgettable memories together.

Things to do recommended for families

Your family will have a blast at Soldier Field, just 6 miles from Woodlawn, enjoying the exciting sports atmosphere. For a peaceful day, visit the Northerly Island Natural Area, 5 miles away, or unwind at The East Bank Club, located 8 miles from Woodlawn, both offering wellness and relaxation vibes.

Things to do recommended for groups

Enjoy a night out at the Chicago Theatre, just 7 miles from Woodlawn, for a mix of culture and entertainment. For outdoor fun, hit the South Shore Golf Course, located 2 miles away. Don’t miss the laughter at Second City, a comedy hub 9 miles from your base.

*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 Woodlawn

When planning your trip—whether you're traveling with a group, with family, bringing along your pets, or seeking extended stays—be sure to prioritize your preferences when filtering options. Here are some helpful booking tips for Vrbo.

  • Traveling to Woodlawn with a group: Think about how many bedrooms you require and any additional features you might want, like a full kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Woodlawn with young kids: Traveling with young kids can be quite demanding. It’s important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Woodlawn: For many, a family vacation isn’t truly fulfilling without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Woodlawn: If you're in search of vacation rentals that offer great savings 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 for the perfect getaway.

Where to stay near Woodlawn

Woodlawn, a vibrant neighborhood in Chicago, offers a unique blend of family-friendly activities and cultural experiences. During your visit, explore nearby neighborhoods that showcase the city's diverse atmosphere, from urban scenery to friendly locals. Enjoy leisurely strolls along residential streets, and immerse yourself in the rich history and charm of the Woodlawn area. Whether you're seeking outdoor adventures or cultural gems, Woodlawn is the perfect base for your Chicago vacation.

  • Chicago: As one of the largest cities in the United States, Chicago is a vibrant urban hub that offers a plethora of experiences for travelers. Woodlawn is nestled within this dynamic city, making it easy to explore everything Chicago has to offer. Known for its rich cultural scene, visitors can enjoy a variety of activities including shopping in bustling districts, catching a show at renowned theaters, or attending events at large arena entertainment facilities. Major landmarks such as sports stadiums and tourist precincts provide endless options for exploration, ensuring that families and city enthusiasts alike will find something to enjoy.
  • Hyde Park: Located a mile away from Woodlawn, Hyde Park is a culturally rich neighborhood known for its educational institutions and historic charm. Travelers flock to this area for family-friendly activities and outdoor experiences. Hyde Park is home to the University of Chicago, a historic college that enhances the neighborhood's vibrant atmosphere. Visitors can explore its beautiful campus, enjoy local shopping, or attend events at various conference venues. The community's commitment to culture is evident in its museums and parks, making it an ideal spot for families and culture seekers.
  • Washington Park: Also situated a mile from Woodlawn, Washington Park offers a blend of family activities and cultural experiences in a lush, urban setting. This neighborhood features beautiful green spaces for outdoor recreation, including the expansive Washington Park itself. Families can enjoy educational opportunities at nearby institutions, visit sports facilities, or shop in local areas. The presence of historical sites and a vibrant community makes Washington Park a delightful destination for those looking to experience the cultural richness of Chicago.

Best time to go to Woodlawn

If you're planning a trip to Woodlawn, 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 hoping to save on your next getaway? One effective strategy is to be flexible with your travel dates, as prices can vary significantly. Additionally, opting for an extended stay often leads to substantial savings. To help you discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's user-friendly Trip Board offers you a dedicated space to plan new adventures, pick up right where you left off, or easily view and organize your travel plans. You can find properties you've saved and booked in the sections for 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 Woodlawn?
In Woodlawn, apartments are the most popular vacation rental option, with about 23 available throughout the neighborhood. These apartments typically offer modern amenities such as fully equipped kitchens, comfortable living areas, and often access to laundry facilities, making them ideal for both short and extended stays. Additionally, there are around 10 condos available, which generally feature similar amenities but may offer shared facilities like pools or fitness centers. For those seeking more space, several vacation houses are also on the market, providing multiple bedrooms, private outdoor areas, and a cozy atmosphere, great for families or larger groups.
Are there any beach house rentals in Woodlawn?
In Woodlawn, Illinois, there are about 11 beach house rentals available, primarily suiting those looking for a peaceful getaway. These properties are typically situated near the shores of Lake Michigan, providing easy access to the lake's recreational activities. Travelers can expect amenities such as fully equipped kitchens, spacious living areas, and outdoor decks or patios for enjoying the scenic views. Many of these rentals are family-friendly, offering multiple bedrooms and communal spaces ideal for gatherings.
How much does it cost to rent a vacation home in Woodlawn?
Prices for vacation rentals in Woodlawn 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 Woodlawn 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 Woodlawn vacation house rentals?
You can find great discounts on house rentals in Woodlawn 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 Woodlawn?
In Woodlawn, popular rental amenities typically include well-equipped kitchens, allowing guests to prepare their own meals. Properties often feature onsite parking for convenience, making it easy for travelers with vehicles. Many rentals also provide coffee and tea makers, great for enjoying a warm beverage at any time. Additionally, accommodations frequently include desks and desk chairs, suiting those who may need a workspace during their stay.
Can I find family house rentals in Woodlawn?
In Woodlawn, Illinois, there are several family-friendly house rentals available—specifically, around 11 options to choose from. This neighborhood offers a mix of spacious homes that cater well to families. Many of these properties feature ample living areas, fully equipped kitchens for preparing meals together, and outdoor spaces where children can play safely.

The area is conveniently located near parks and recreational facilities, making it easy for families to enjoy outdoor activities. Nearby attractions include the beautiful Washington Park, which offers playgrounds and walking paths, and the historic sites within the larger Chicago area, providing plenty of opportunities for exploration.
Can I rent a vacation home with a pool or hot tub in Woodlawn?
In Woodlawn, Illinois, there are several vacation homes available for rent that feature pools and hot tubs. This charming community offers a range of accommodations suitable for families and groups looking for a relaxing getaway. Many of these properties come equipped with private hot tubs, providing a superb spot to unwind after a day of exploring the local area. Additionally, travelers can expect amenities like fully equipped kitchens, spacious living areas, and outdoor spaces for social gatherings.
Are there any Woodlawn vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Woodlawn 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 Woodlawn?
Yes, you can book pet-friendly vacation rentals in Woodlawn, Illinois. The area offers a selection of homes that cater to travelers with pets, ensuring a comfortable stay for both you and your furry companions. Many of these rentals come equipped with amenities such as spacious outdoor areas, fully equipped kitchens, and cozy living spaces, making them ideal for families or groups.

Woodlawn is conveniently located near several parks where you can enjoy time outdoors with your pets. The nearby Washington Park provides walking trails and open spaces, superb for leisurely strolls or picnics. Additionally, the area features pet-friendly cafes and shops, enhancing your experience while exploring the neighborhood.
Can I find long-stay vacation rentals in Woodlawn?
A long-stay vacation rental in Woodlawn 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 Woodlawn for a vacation rental?
The best time to visit Woodlawn for a vacation rental is during the peak season from May to July. This period is particularly vibrant, as travelers flock to the area to enjoy outdoor activities in the warm weather. With temperatures typically ranging from the low 60s to high 80s Fahrenheit, visitors can comfortably explore local parks, enjoy picnics, and participate in various community events.

July stands out as the most popular month, offering a lively option filled with recreational opportunities and social gatherings. This is an ideal time for families and adventure seekers who enjoy engaging with the local culture and taking advantage of the beautiful surroundings.

For those looking to save a bit while still enjoying the charm of Woodlawn, consider visiting in December. This month provides a quieter experience, allowing for peaceful exploration of the area's winter scenery. Although it's a low season, it can be a lovely time to enjoy cozy accommodations and local holiday festivities.
Are there any remote work vacation rentals in Woodlawn?
In Woodlawn, Illinois, there are numerous vacation rentals available for remote work, with around 33 options to choose from. Many of these properties are equipped with essential amenities to facilitate a productive working environment, including dedicated desks, Wi-Fi, and internet service from third-party providers. Travelers can expect comfortable accommodations that often feature additional perks like cozy workspaces, spacious living areas, and kitchen facilities for convenient meal preparation. The area's proximity to Chicago also allows for easy access to urban amenities while enjoying a quieter setting. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Woodlawn vacation rental?
Book your Woodlawn 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 Woodlawn, Illinois, United States of America?
In Woodlawn, Illinois, visitors can explore a variety of attractions that showcase the neighborhood's historical and cultural significance. One of the main highlights is the historic Stony Island Arts Bank, which serves as a community center and art gallery, offering exhibitions and events that reflect the local heritage. The area also features beautiful parks like Washington Park, which includes sports facilities and scenic walking paths, ideal for outdoor activities.

Additionally, the nearby University of Chicago offers access to its impressive campus and the Oriental Institute Museum, which houses ancient artifacts from the Near East. The surrounding neighborhoods, such as Hyde Park, provide further opportunities to enjoy cultural sites, including the Museum of Science and Industry, one of the largest science museums in the world.
Can I change or cancel my Woodlawn home rental booking on Vrbo?
To find Woodlawn 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 Woodlawn 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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