--- title: "Woodlawn Holiday Rentals, Chicago: Private House Rentals | Vrbo" canonical: "https://www.vrbo.com/en-gb/holiday-rentals/united-states/illinois/cook-county/chicago/woodlawn" language: en-GB market: GB currency: GBP prices_as_of: 2026-11-15T10:01:46Z --- # Woodlawn holiday lettings ![A wooden bridge over a calm river, surrounded by lush greenery and a distant building.](https://images.trvl-media.com/place/507388/55006cfe-251b-4687-a3b4-4db058849ab1.jpg?impolicy=resizecrop&rw=1920&ra=fit&ch=480) We found 84 holiday rentals — enter your dates for availability Discover a selection of 9 homes and other holiday rentals in Woodlawn that are perfect for your trip. Holiday rentals provide the best amenities for your family, friends or furry companion, such as a fireplace and a washer and dryer. You're sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible. ## Find spaces that suit your style [Search for Houses](https://www.vrbo.com/search?destination=Woodlawn%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6132422&latLong=41.778848%2C-87.594559&adults=2&startDate=2026-11-29&d1=2026-11-29&endDate=2026-12-01&d2=2026-12-01&property%5Ftype%5Fgroup=house) House [Search for Condos/Apartments](https://www.vrbo.com/search?destination=Woodlawn%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6132422&latLong=41.778848%2C-87.594559&adults=2&startDate=2026-11-29&d1=2026-11-29&endDate=2026-12-01&d2=2026-12-01&property%5Ftype%5Fgroup=apartment%5For%5Fcondo) Condo/Apartment [search for cabins](https://www.vrbo.com/search?destination=Woodlawn%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6132422&latLong=41.778848%2C-87.594559&adults=2&startDate=2026-11-29&d1=2026-11-29&endDate=2026-12-01&d2=2026-12-01&property%5Ftype%5Fgroup=cabin) Cabin [search for cottages](https://www.vrbo.com/search?destination=Woodlawn%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6132422&latLong=41.778848%2C-87.594559&adults=2&startDate=2026-11-29&d1=2026-11-29&endDate=2026-12-01&d2=2026-12-01&property%5Ftype%5Fgroup=cottage) Cottage [search for villas](https://www.vrbo.com/search?destination=Woodlawn%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6132422&latLong=41.778848%2C-87.594559&adults=2&startDate=2026-11-29&d1=2026-11-29&endDate=2026-12-01&d2=2026-12-01&property%5Ftype%5Fgroup=villa) Villa [search for chalets](https://www.vrbo.com/search?destination=Woodlawn%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6132422&latLong=41.778848%2C-87.594559&adults=2&startDate=2026-11-29&d1=2026-11-29&endDate=2026-12-01&d2=2026-12-01&property%5Ftype%5Fgroup=chalet) Chalet ## Find properties near top attractions in Woodlawn ![A wooden bridge over a calm river, surrounded by lush greenery and a distant building.](https://images.trvl-media.com/place/507388/55006cfe-251b-4687-a3b4-4db058849ab1.jpg?impolicy=fcrop&w=600&h=400&p=1&q=medium) 1 ###### [Jackson Park](https://www.vrbo.com/en-gb/search?regionId=507388&startDate=&endDate=&locale=en%5FGB&rfrrid=slp) ## Find the best place to stay - Woodlawn ### [1\. Spacious 5-bedroom house in Chicago with AC Near Obama Center & UChicago](https://www.vrbo.com/en-gb/p5379661vb?containsVideo=false) ![Image of Spacious 5-bedroom house in Chicago with AC Near Obama Center & UChicago](https://media.vrbo.com/lodging/134000000/133550000/133541800/133541754/b2eb4352.jpg?impolicy=resizecrop&ra=fit&rw=455&rh=455) - Guest rating: 10/10 (Exceptional, 1 review) Sleeps 10 · 5 bedrooms · 2+ bathrooms ### [2\. 3BR near U Chicago and Obama Center, Easy Parking](https://www.vrbo.com/en-gb/p5137480vb?containsVideo=false) ![Image of 3BR near U Chicago and Obama Center, Easy Parking](https://media.vrbo.com/lodging/128000000/127060000/127050900/127050868/2b628b5a.jpg?impolicy=resizecrop&ra=fit&rw=455&rh=455) - Guest rating: 9.6/10 (Exceptional, 19 reviews) Premier Host Sleeps 6 · 3 bedrooms · 1 bathroom ### [3\. Bright Vintage U of C Center Condo with WiFi, AC in enjoyable Chicago](https://www.vrbo.com/en-gb/p4573924vb?containsVideo=false) ![Image of Bright Vintage U of C Center Condo with WiFi, AC in enjoyable Chicago](https://media.vrbo.com/lodging/116000000/115930000/115925300/115925246/517f055e.jpg?impolicy=resizecrop&ra=fit&rw=455&rh=455) - Guest rating: 8.4/10 (Very good, 10 reviews) Sleeps 6 · 3 bedrooms · 3 bathrooms ### [4\. Luxe Loft vibe –4BR/3BA Apt– King Suite-11 minutes from downtown-Families-Groups](https://www.vrbo.com/en-gb/p4694726vb?containsVideo=false) ![Image of Luxe Loft vibe –4BR/3BA Apt– King Suite-11 minutes from downtown-Families-Groups](https://media.vrbo.com/lodging/119000000/118710000/118707800/118707787/3da19de7.jpg?impolicy=resizecrop&ra=fit&rw=455&rh=455) - Guest rating: 9.8/10 (Exceptional, 8 reviews) Premier Host Sleeps 8 · 4 bedrooms · 3 bathrooms ### [5\. Lovely three bedroom Loft, University Of Chicago, Obama Library](https://www.vrbo.com/en-gb/p5105403vb?containsVideo=false) ![Image of Lovely three bedroom Loft, University Of Chicago, Obama Library ](https://media.vrbo.com/lodging/127000000/126480000/126471000/126470922/840bf78d.jpg?impolicy=resizecrop&ra=fit&rw=455&rh=455) - Guest rating: 9.6/10 (Exceptional, 12 reviews) Premier Host Sleeps 6 · 3 bedrooms · 2+ bathrooms ### [6\. Cozy 3BR Near Obama Presidential Center, Hyde Park & UChicago](https://www.vrbo.com/en-gb/p4218192vb?containsVideo=false) ![Image of Cozy 3BR Near Obama Presidential Center, Hyde Park & UChicago](https://media.vrbo.com/lodging/110000000/109370000/109364400/109364310/e167cf45.jpg?impolicy=resizecrop&ra=fit&rw=455&rh=455) - Guest rating: 9.6/10 (Exceptional, 8 reviews) Premier Host Sleeps 6 · 3 bedrooms · 1 bathroom ### 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 Woodlawn? Prices for holiday 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](https://www.vrbo.com/en-gb/search?regionId=6132422&sort=PRICE%5FLOW%5FTO%5FHIGH) to more spacious homes. To get the best value, book early and take advantage of [Vrbo’s free rewards program](https://www.vrbo.com/en-gb/welcome-one-key). ### Are there any discounts for Woodlawn holiday 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. ### Are there any Woodlawn holiday rentals with parking? Vrbo offers a wide selection of [holiday rentals in Woodlawn with parking](https://www.vrbo.com/en-gb/search?regionId=6132422&amenities%5Ffacilities%5Fgroup=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 Woodlawn? A long-stay holiday rental in Woodlawn 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 Woodlawn for a holiday rental? The best time to visit Woodlawn for a holiday rental is during the peak season from May to July, particularly in July when the weather is at its warmest and most inviting. This period attracts families and adventure seekers keen to explore the charming small-town atmosphere of Woodlawn and the surrounding areas. With temperatures typically ranging from 20 to 30 degrees Celsius, outdoor activities like hiking, biking, and picnicking are superb for making the most of the sunny days. Visitors can enjoy local festivals and events that often take place during these months, bringing together the community and providing a vibrant setting. The lush landscape and blooming flowers in spring create a picturesque setting for sightseeing and exploring nearby attractions. If you're looking for a more budget-friendly option, consider visiting in December, when you can experience the tranquillity of the town during the quieter winter months. This time of year is superb for those who appreciate a peaceful retreat and the opportunity to enjoy the festive spirit without the crowds. ### How early should I book a Woodlawn holiday rental? Book your Woodlawn 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 Woodlawn, Illinois, United States of America? In Woodlawn, visitors can explore a variety of attractions that reflect the area's rich history and cultural significance. A highlight is the University of Chicago, located nearby, which offers beautiful architecture and gardens, as well as the renowned Oriental Institute Museum that showcases ancient artefacts from the Near East. The historic site of the Woodlawn Cemetery is also noteworthy; it features top graves and serene landscapes. For those interested in outdoor spaces, the nearby Washington Park provides ample green areas for walking and picnicking, along with recreational facilities. Additionally, the neighbourhood is close to the vibrant Hyde Park area, where one can enjoy shopping, dining, and cultural events, including the famous Museum of Science and Industry. ### Can I change or cancel my Woodlawn home rental booking on Vrbo? To find Woodlawn holiday rentals with free cancellation, just use Vrbo's handy "[Free cancellation](https://www.vrbo.com/en-gb/search?regionId=6132422&free%5Fcancellation%5Fgroup=free%5Fcancellation)" 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](https://www.vrbo.com/en-gb/list) 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 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™](https://www.vrbo.com/en-gb/tlp/trust-and-safety/care-guarantee), 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](https://www.vrbo.com/en-gb/helpcenter/?articleId=40104), 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](https://www.vrbo.com/en-gb/why/trip-planning) makes organising group trips easy and stress-free. 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[Kenwood Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/illinois/cook-county/chicago/kenwood) - [Hyde Park Hair Salon Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/illinois/cook-county/chicago/hyde-park/hyde-park-hair-salon) - [Griffin Museum of Science and Industry Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/illinois/cook-county/chicago/hyde-park/chicago-museum-of-science-and-industry) - [Chicago Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/illinois/cook-county/chicago) - [Rainbow-Push Headquarters Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states-of-america/illinois/cook-county/chicago/kenwood/rainbow-push-headquarters) - [Oak Woods Cemetery Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/illinois/cook-county/chicago/grand-crossing/oak-woods-cemetery) - [Grand Boulevard Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/illinois/cook-county/chicago/grand-boulevard) - [Englewood Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/illinois/cook-county/chicago/englewood) - [4944 S Woodlawn Ave Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/illinois/cook-county/chicago/kenwood/4944-s-woodlawn-ave) - [Chatham Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/illinois/cook-county/chicago/chatham) - [Barack Obama Residence Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states-of-america/illinois/cook-county/chicago/kenwood/barack-obama-residence) - [Greater Grand Crossing Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/illinois/cook-county/chicago/grand-crossing) - [Greater Salem Baptist Church Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/illinois/cook-county/chicago/grand-crossing/greater-salem-baptist-church) - [Avalon Park Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/illinois/cook-county/chicago/avalon-park) ## Other language versions ```yaml hreflang: x-default: https://www.vrbo.com/vacation-rentals/usa/illinois/chicago/south-side/woodlawn en-GB: https://www.vrbo.com/en-gb/holiday-rentals/united-states/illinois/cook-county/chicago/woodlawn en-AU: https://www.stayz.com.au/d/166474/woodlawn pt-BR: https://www.vrbo.com/pt-br/alugue-temporada/estados-unidos/illinois/condado-de-cook/chicago/woodlawn ja-JP: https://www.vrbo.com/ja-jp/%E5%AE%BF%E6%B3%8A/%E3%82%A2%E3%83%A1%E3%83%AA%E3%82%AB/%E3%82%A4%E3%83%AA%E3%83%8E%E3%82%A4%E5%B7%9E/%E3%82%AF%E3%83%83%E3%82%AF%E9%83%A1/%E3%82%B7%E3%82%AB%E3%82%B4/%E3%82%A6%E3%83%83%E3%83%89%E3%83%A9%E3%83%BC%E3%83%B3 es-ES: https://www.vrbo.com/es-es/alquiler-vacacional/estados-unidos/illinois/cook-county/chicago/woodlawn en-US: https://www.vrbo.com/vacation-rentals/usa/illinois/chicago/south-side/woodlawn en-CA: https://www.vrbo.com/en-ca/vacation-rentals/united-states/illinois/cook-county/chicago/woodlawn en-NZ: https://www.bookabach.co.nz/d/166474/woodlawn sv-SE: https://www.vrbo.com/sv-se/semesterbostad/usa/illinois/cook-county/chicago/woodlawn de: https://www.fewo-direkt.de/d/166474/woodlawn de-AT: https://www.vrbo.com/de-at/urlaubsunterkunft/vereinigte-staaten/illinois/cook-county/chicago/woodlawn it-IT: https://www.vrbo.com/it-it/case-vacanze/stati-uniti-damerica/illinois/contea-di-cook/chicago/woodlawn en-SG: https://www.vrbo.com/en-sg/holiday-accommodation/united-states/illinois/cook-county/chicago/woodlawn ```