Lake house holiday rentals in Chicago

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Top-rated lakehouse rentals in Chicago

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Guest favourite

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.

Superhost

Home in Des Plaines

4.83 out of 5 average rating, 42 reviews

House in the Park- 5 Min from O'Hare.

Bring the whole family to this great place with lots of room across the street for fun fishing, golfing, bike track, vally ball court, picnic area, kids play ground, water splash, boat riding, Foxtail on the Lake resturant that serve modern Mediterranean cuisine. The house is only 5 minutes away from O'Hare Airport, ALLSTATE Arena, River Casino, 10 min to Stevenson Convention Center in Rosemont, 20 min to Wrigley Feild/25 min to Chicago downtown, and only 35 min to Six Flags Great America Park.

Guest favourite

Home in Hyde Park

5 out of 5 average rating, 17 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.

Top Guest favourite

Home in Evanston

5 out of 5 average rating, 101 reviews

Larimer Park Carriage House

Charming, historic carriage house only a few short blocks from Evanston's best shopping, restaurants and beaches. Home offers 2 bedrooms each with private ensuite bathrooms. Larger bedroom has king size bed and bathroom with large shower. Second bedroom has queen bed and shower/tub combo. Open layout on main floor with huge sectional sofa, 4-person dining table, and fully equipped kitchen with dishwasher. Laundry in home + parking space! Nestled in historic neighborhood next to Larimer Park

Guest favourite

Home in Whiting

4.84 out of 5 average rating, 153 reviews

The Spa of Downtown Whiting

so close to Chicago but so far away. NEWLY REMODELED AND COMPLETELY FURNISHED. There's so much to enjoy in this incredible converted 2 flat, now a single unit. WE COMPLETELY RIPPED ON AND REDID THE ENTIRE INTERIOR. 1ST Flr-spa w/ 2 person jacuzzi, shower, continuous hot water, family room, kitchen 2nd flr, sitting room w/ TV and surround sound, 2 bedrooms, w/ bathroom and bath/shower. -FRONT BALCONY, -SPEAKERS THROUGHOUT -BLOCKS FROM THE BEACH & WOLFE LAKE -PERFECT LOCATION FOR PIEROGIFEST

Guest favourite

Home in Old Town

4.86 out of 5 average rating, 140 reviews

Huge Home *Prime Spot *Yard *Parking *Fireplace

Unique opportunity to rent an original Victorian home in historic Old Town. Only listing of its kind! Walk to almost everything Chicago has to offer- Downtown, Magnificent mile, restaurants, bars, boutiques; Lincoln Park and North ave beach from this three-level house. 5 bedrooms, 3.5 baths, 2 fully stocked kitchens, 2 car garage, back yard, laundry, pets welcome - what else can you possibly need? Space is expandable from a smaller family to a group of 22. Message me if you have any questions!

Superhost

Home in Woodlawn

4.83 out of 5 average rating, 121 reviews

Woodlawn Oasis: 5-15 Mins from Food, Fun, Dining

Experience comfort and convenience in our modern stylish home. With 3 spacious bedrooms, 2.5 bathrooms, an open concept kitchen, and a backyard patio, there's plenty of room to relax and unwind. Our home is conveniently located near the highway, shopping, and restaurants. 5 mins from the University of Chicago and the Beach.. 10-15 mins from Hyde Park and Downtown, Soldiers Field, and lots of other sights in Chicago. Perfect place to stay if you are coming with a group!! Book your stay now.

Top Guest favourite

Home in Westmont

4.93 out of 5 average rating, 30 reviews

Westmont,Il 4/3 on the Lake

We may take a refundable deposit. We must say this because our direct booking site is linked. A lovely place on the lake in summer we rent entire house. This is a home that is split into a duplex. One side we have 3 bedrooms 2 baths. The other side is 1 bedroom and 1 bath. Both sides have separate entrances and decks. Enjoy the beautiful view while staying. You have access to entire house and yard except garage with this listing. This listing is for renting both sides. They do not connect.

Guest favourite

Home in Lake Zurich

4.9 out of 5 average rating, 21 reviews

Quiet 3 BR house Roku, Office with printer

No parties but have a good time. This house is on well water which some people do not like at all. The refrigerator is stocked with bottled water and there is a Britta pitcher as well. Handicap accessible. Smart TV and Wifi available. Kitchen basics but more available upon request especially for long-term. Accomodations for the eight include someone on the sofa/air mattress. There's only one bathroom. 2 rooms are up stairs steeper than some prefer. Main BR and bathroom on 1st floor.

Guest favourite

Home in Barrington

5 out of 5 average rating, 48 reviews

ON RIVER Barrington Home + Deck & Views

Watch as the sun sets over the Fox River from the spacious deck of this 4-bedroom, 3.5-bathroom vacation rental each night. This fully-equipped home has it all: kayaks, scooters, board games, and a fire pit to cozy up next to after a long day of adventure. Though it may be tempting to spend your days lounging at the private community beach just 100 yards away, don’t forget to check out the charming shops, exciting events, and delicious dining spots that downtown Barrington has to offer.

Guest favourite

Home in Lake View

4.9 out of 5 average rating, 141 reviews

Spacious Two Story Luxurious Home w/Outdoor Deck!

Our home is in a quiet neighborhood, on a corner with abundant space and natural light. There are two spacious levels with two bedrooms upstairs and one downstairs. The large outdoor brand new deck was designed for barbecuing, star-gazing or just relaxing. Beautifully polished wood floors with a modern kitchen make this home ideal. A claw foot soaking tub is perfect for the end of a day and truly ensures a relaxing stay and a deep, refreshing sleep. Free parking!

Top Guest favourite

Home in Carol Stream

4.91 out of 5 average rating, 104 reviews

Lake House Hot Tub-Billiards-Kayak Waterfront Stay

Our beautiful home is the perfect place to gather with friends & family, relax, refresh, fish, have fun with your loved ones. It's the perfect home away from home with great views of the lake and on a quiet cul-de-sac. Stunning views of the lake while grilling or the firepit from the completely upgraded patio & the hot tub 🥂 🐶Up to 2 furry babies are allowed & they'll love the almost 1 acre fenced-in yard! (pet fee is extra & must be included at time of booking)