House vacation rentals in Woodlawn

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Top-rated house rentals in Woodlawn

Guests agree: these houses are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Bridgeport

4.95 out of 5 average rating, 140 reviews

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking

1 King, 1 Queen, 1 Sofa Bed, 2 Air Mattresses (1 Full, 1Queen) 1 Pack n Play Enjoy your stay in this cozy modern home that sits on an oversized lot with luxury amenities and a spacious front yard with exceptional landscaping. The property has a car port in back which allows parking for 2 cars. The ideal getaway to grill up some food and relax in the jacuzzi hot tub year round! We are pet friendly! NO CHORES! Please reach out with any questions you may have before booking Hot tub 5-6 Person Spa

Guest favorite

Home in North Park

4.96 out of 5 average rating, 183 reviews

Chicago River House -BBQ Oasis now open!

Close to must see Chicago restaurants and nightlife, yet nestled in nature! This 1937 Print Shop is seated between the Chicago River & Forest Preserves, with trails & river walks, 3 miles to the beach, near Lake Shore Drive & 90/94, nearby Lincoln Square , Andersonville, and seasonal waterfalls, brunch nearby. This 2-bed, 2-bath home one level. 5star Chef's kitchen 9’ x 15’ HD projector, comfy beds, double shower head shower room, near nature. Relax on our private patio and glowing furniture

Guest favorite

Home in Whiting

4.96 out of 5 average rating, 130 reviews

MiniGolfHouse-Chicago Close Beach & Indoor Fun!

🌆 30min drive to downtown Chicago ⭐️ Near Horseshoe Casino, Lake Michigan, Whihala Beach, Whoa Zone ⛳️ Heated basement with mini golf, arcade games and big TV 🐶 Pet fee: $150 (Must let us know BEFORE BOOKING if bringing a pet) ⭐️ Close To: Wolf Lake, Indiana Dunes, HardRock 🏠 cots, air mattress, futon sofa in basement 🍼 pack & play, high chair avail ❤️ Guests love: -short drive into Chicago -comfortable beds -indoor mini golf -nearby shops & food -heated bidet toilet seats

Guest favorite

Home in Wicker Park

4.97 out of 5 average rating, 117 reviews

UP-SCALE Wicker Park 4BD/3.5BA HOME (+garage)

Escape into this Wicker Park Masterpiece! Guests love this home because: - Steps away from top-notch restaurants/entertainment on bustling Division St. - Close to every popular attraction that makes Chicago so great - Luxurious interior filled with natural light - Open-floor plan for entertaining! - City skyline views from top floor! - Fast WiFi (1,000 mbps) - Large attached garage! - Beautiful custom built-ins - Next to modern park and playground! - 10 minute walk from blue line (CTA L)

Top guest favorite

Home in Berwyn

4.98 out of 5 average rating, 161 reviews

Retro Modern Bungalow | free parking | fire pit

Experience the city in style at our Retro Modern Bungalow, the perfect pad for up to 4 friends. Featuring two spacious bedrooms—each with a king bed and luxury linens—a propane fire pit and a fully fenced, pup-friendly backyard. Enjoy central HVAC, speedy WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage or catch the train a few blocks away.

Guest favorite

Home in Chicago

4.88 out of 5 average rating, 153 reviews

Boho Chic Coach House 30Min to downtown W/ Parking

Whether your looking to stay near family or be close to Downtown. This place has it ALL! This coach house is located in Mt greenwood which is one of the safest neighborhoods in the City of Chicago. It is home to many police, firefighters and teachers. Downtown is a quick 30 minute drive and there are also many bars and restaurants in walking distance. The home has been totally renovated and stocked with all the essentials. All you need to do now is pack your bags and enjoy your vacation.

Guest favorite

Home in Forest Park

4.91 out of 5 average rating, 302 reviews

Charming dog friendly 2-Bath Bungalow Near Chicago

Steps from the cobblestone streets of Forest Park into our cheery bungalow, perfect for artistic souls and business travelers alike. Inside is a design savvy mix of mid-century furniture, comfy beds, and art from around the globe. Built in 1908, it boasts modern amenities you desire without sacrificing vintage charm. Minutes away from local shops, restaurants. Just off I-290, Blue Line CTA, 20. min drive to ORD, Midway & Downtown Chicago. Plus we’re dog-friendly-- bring up to 2 pups!

Top guest favorite

Home in Oak Park

4.97 out of 5 average rating, 145 reviews

Garden: Clean, Central Location & Parking Sleeps 4

Our Oak Park, recently remodeled garden unit is 3 blocks to the train with free parking in upscale, safe, walkable Oak Park. Enjoy some time in our little urban farm. Check out the gardens and visit our 6 friendly hens. This non-smoking studio with a kitchenette is perfect for tourists, families, or business travelers. We require no check-out chores. Easy highway and airport access. No parties, 4 guests max. Booking age, 25 or at least one 5 ⭐️ review. Visit profile for more units.

Top guest favorite

Home in West Loop

4.98 out of 5 average rating, 363 reviews

Cozy garden apartment historic Jackson Bvld.

Just a short walk to the United Center our cozy 1 bdrm garden apt is located on Historic Jackson Blvd's tree lined st. Stop back & warm up by the fireplace before heading out to near by shopping & restaurants. Less than an hour from Midway or O'Hare. Walking distance to Randolph St. Restaurant Row, Little Italy, Greek Town, Union Pk, Fulton Warehouse Dist, Rush Hospital and UIC. A quick train/bus to The Loop, Theater Dist, Mag Mile, Wicker Pk. Free, convenient street pkg.

Top guest favorite

Home in Wicker Park

4.97 out of 5 average rating, 264 reviews

Division St Designer Home In Heart of Wicker Park

Stay in the best location in the heart of the East Village/Wicker Park neighborhoods! Located on a quiet tree-lined street, you’ll be only steps to the cafes, restaurants, bars, and shops that flank trendy Division Street; a short walk to the vibrant Chicago Ave and Milwaukee Ave restaurant & retail corridors. Just off the Division Blue Line “L” stop, we’re just a quick train ride to both the Downtown Loop (8 minutes) and O’Hare International Airport (35 minutes).

Guest favorite

Home in Blue Island

4.82 out of 5 average rating, 210 reviews

Warm and comfortable inviting Suburban home !

160 year old land mark community, Framed cedar bevel siding 2 story home, front porch , 10 ft high ceilings, kitchen canned lighting home. 6 feet fence In closed yard, whole house water filtration system , Quite neighborhood with sidewalks . 19 miles to downtown Chicago , Metra train station and bus route, in walking distance . driving to the city of Chicago 5 minutes to major expressways . Host is willing to be available for any and all information 24/7.

Guest favorite

Home in Portage Park

4.98 out of 5 average rating, 213 reviews

The Evergreen House

Relax and feel at home on the first floor apartment (completely private) of my Chicago 2-Flat. This home away from home is well stocked with anything that you might need whether you are staying for 2 nights or 2 months. There are 3 televisions with Wifi and Netflix throughout the apartment. There is a nice backyard that you are welcome to use and street parking is free. Washer and Dryer available in the basement. The highways and bus are also nearby.