House vacation rentals in Woodlawn, Chicago

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Top-rated house rentals in Woodlawn, Chicago

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Guest favorite

Home in Lake View

4.87 out of 5 average rating, 128 reviews

Soak Up Mid-Century Style in Wrigleyville and Boystown

This is an architecturally significant (3-bedroom 3.5-bathroom) home by noted Las Vegas architect Homer Rissman. We are located in the heart of East Lakeview, just half a block from Lake Michigan and Lincoln Park, and blocks away from Wrigley Field and Boystown. Smart TVs (with Netflix, Hulu, Amazon Prime) are located in the shared main level TV lounge, and also the lower level lounge. Entire home I like in-person check-in but full privacy is offered You will receive a link with detailed instructions within 24 hours of your check-in. If you have a U.S. mobile number, you will also receive a text message FULL DISCLOSURE: If you haven't used a lockbox (or don't know how to), self-check-in isn't for you. Your check-in should be in person. Lakeview is home to two of the most vibrant sports, nightlife, and theater scenes in Chicago: Wrigleyville and Boystown. Explore souvenir shops and casual eateries by day, and hop from bar to bar along Clark, Addison, and Sheffield Avenues by night. You walk to Treasure Island (half block), Jewel Osco (2 minutes), Whole Foods (4 minutes), Lakeview Athletic Club (4 minutes), XSports Fitness (5 minutes), Walgreens (3 blocks), bars and restaurants aound the corner. Close to multiple buses on Lake Shore Drive. Grab a bus to downtown in 15 minutes You will have to climb one flight of stairs for all bedrooms Street parking is free on the east side of Broadway. The west side requires 383 permits. Please, read the signs.

Guest favorite

Home in Wicker Park

4.92 out of 5 average rating, 271 reviews

Cool Quiet Coach House, Private Access + Patio

Retreat to the brick patio of this lovingly renovated home after a long day traversing the neighborhood. The interior is an expression of creativity, greyscale walls, rustic accents, and a varied selection of art and wall hangings tie in the decor. Split Level Floor plan. 1st floor = Living, Eat in Kitchen, bedroom 1 and bathroom. 2nd Floor = 2nd bedroom , bath and an additional sleeping area and desk area. Also features a gorgeous shared yard. The entire coach house is yours!! The coach house is set back behind a 2 unit building and the yard is shared between both. We are available via text or airbnb messaging and try to respond quickly. Please reach out anytime if you need anything at all. Extra supplies, neighborhood recommendations or tips in the neighborhood. The home is located on the border of Wicker Park and Bucktown which is Chicago's original hub of cool. It is a vibrant enclave of culture and commerce, explore vintage finds, record stores, and plenty of indie shopping in this trendy part of town The 24 hour Blue Line EL train is just a 5 minute walk. Door to Door it's only 25 minutes to Millennium park. (5 min walk to the blue line, 10 min ride on the train, 10 minute walk to the Park). The neighborhood is pedestrian and bike friendly , the 606 trail is just a few blocks away also.

Guest favorite

Home in Hyde Park

5 out of 5 average rating, 16 reviews

Amazing historic campus mansion!

This stylish campus mini mansion is perfect for group trips in the historic Hyde Park neighborhood. A cheerful, modern renovation of a historic home, with original woodwork, underfloor bathroom heating and leaded windows. Easy access to Uchicago, the lakefront, Chicago marathon, McCormick trade shows, the Museum of Science & Industry or exploring our vibrant city. Our spotlessly clean property helps you experience everything Chicago has to offer. Hosted by a very experienced all 5 star host.

Guest favorite

Home in Lincoln Park

5 out of 5 average rating, 12 reviews

Top Floor in Historic Old Town!

Unbeatable Location in Historic Old Town Triangle! This charming top-floor apartment is on a quiet cul-de-sac in the heart of Old Town Triangle, steps from St. Michael’s Church, North Ave Beach, Lincoln Park Zoo, and Wells Street’s entertainment district. The sun-filled space features an oversized private patio, and 3 bedrooms with queen beds, closets, and dressers. The spacious kitchen and dining areas are perfect for gatherings. The “L” stop is just two blocks away for easy access to the city.

Top guest favorite

Home in Elmhurst

4.92 out of 5 average rating, 24 reviews

Premier 5BR/3BA Modern Retreat with King Suite!

Beautiful 5BR/3BA Retreat in a Chicagoland suburb! ☆ Newly renovated and stylish, this spacious home features a modern open layout, luxurious bedrooms, a gourmet kitchen, and elegant bathrooms. Explore the vibrant Chicagoland neighborhood with local shops and parks, then come home to relax in peace. Conveniently located in a prime area, a quick drive from the airport or Oak Brook shopping mall. Ideal for families, groups, or anyone seeking comfort and convenience. Book now for a memorable stay!

Superhost

Home in Logan Square

4.84 out of 5 average rating, 100 reviews

California Cottage/4br prime location Logan Square

Incredible location in Logan Square! Walking distance from dozens of restaurants, breweries, bars, nightlife, the square, the farmers’ market and much more. Free street parking in front. 2 blocks from 90/94 and close to the blue line train which goes to many of Chicago’s iconic neighborhoods, downtown, and directly to O’ Hare airport. Beautiful house with high ceilings on the 1st floor. Lovely kitchen with nice appliances. 2 cozy bedrooms upstairs. One with a queen and the other has 3 twins.

Superhost

Home in Glendale Heights

4.8 out of 5 average rating, 44 reviews

Spacious 4 Bed Room suburban home

Spacious and one of its kind 4 bed room 2 storied house can host up to 8-10 adults and kids. 1st Floor with living, Family, kitchen and dining. 2nd Floor with master king bed with whirlpool tub, 3 Queen beds and laundry closet. In the middle of a small town has easy and quick access to highways, retails, restaurants, hospitals, fire districts, parks, library, schools and groceries. Offers neighborhood living style and would be a perfect for your family vacation or out of town work location.

Superhost

Home in Homewood

5 out of 5 average rating, 6 reviews

Fore! Peace & Love @ Golf House

Welcome to "The Golf House"! Our 4-bed, 3-bath home sleeps 8 people comfortably and, features an open living space with a stunning golf course view, a full kitchen, and a huge deck. Enjoy natural sunlight or the stars through the skylight both in the master bedroom and bathroom. The home has hardwood floors, and TVs in each bedroom. Plus, a heated meditation room for relaxation. Ideal for families, women retreats, networking events etc. Experience luxury and tranquility right by the greens!

Guest favorite

Home in Elmhurst

4.87 out of 5 average rating, 23 reviews

Enamored in Elmhurst

Have fun with the whole family at this beautifully renovated house with and open floor plan, fully stocked kitchen, 4 bedrooms, 2 bathrooms with smart tv's in all the bedrooms and quick reliable wifi for all to enjoy. Home is located only minutes from the highways, enjoy the deck right off the living room and overlooking a private yard . House also has a fully finished basement with 2 of the bedrooms, a full bathroom and a theater room with a sectional sleeper sofa if more space is needed.

Top guest favorite

Home in Avondale

5 out of 5 average rating, 12 reviews

Alluring Avondale Abode

Welcome to Alluring Avondale Abode, the perfect vacation rental for your next family trip or group getaway. A pet-friendly paradise, centrally located for easy travel to all the top attractions. A spacious kitchen, beautiful backyard deck, and patio create a wonderful backdrop for entertaining and relaxing. Find an array of fun games to keep all ages occupied. Book now and experience the laid-back vibe and unbeatable amenities that will make your vacation truly unforgettable.

Superhost

Home in Des Plaines

4.85 out of 5 average rating, 101 reviews

Cozy Home by O'Hare + EV Plug

Family-friendly 3BR/2BA home in Des Plaines! Enjoy arcade games, board games, and an EV charger. Nestled in a quiet neighborhood near parks, shopping, and entertainment. Just minutes from Des Plaines Theatre, Rivers Casino, Mystic Waters, and Fashion Outlets of Chicago. Ideal for families or groups seeking comfort, fun, and convenience with easy access to top attractions and O'Hare Airport. Your perfect home base for exploring the Chicago area!

Top guest favorite

Home in Addison

4.96 out of 5 average rating, 83 reviews

Home in Unincorporated Addison. RV & Pet Friendly

Your family will be close to everything when you stay at this centrally-located place. This house is extremely family friendly. It has 4 bedrooms and three baths. It has been recently remodeled inside and out. The yard is close to 3/4 acres and has a kids playground and firepit. The driveway is long and can park a long RV if needed. This is a quiet location. Fully Fenced in Yard with lights all around the house. Very safe location.