Lake house vacation rentals in Chicago

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Top-rated lake house rentals in Chicago

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Guest favorite

Home in Chicago

4.87 out of 5 average rating, 115 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.

Sep 9 – 16

G$168,798 GYD per night

Guest favorite

Home in Evanston

5.0 out of 5 average rating, 54 reviews

Larimer Park Carriage House

Enjoy park views from this charming historic carriage house located a few short blocks from Evanston's best shopping, restaurants and beaches. Built to accompany the home of notable Chancellor Livingston Jenks, this carriage house boasts 2 bedrooms each with premium mattresses, ample closets and private ensuite bathrooms. Enjoy cooking in the fully equipped kitchen. Cozy up on the huge sectional sofa and enjoy movies & games. Fast Wi-Fi, Laundry + On-site host is there for any of your needs!

Mar 19 – 26

G$48,597 GYD per night

Superhost

Home in Whiting

4.83 out of 5 average rating, 120 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

Sep 9 – 16

G$36,956 GYD per night

Guest favorite

Home in Whiting

5.0 out of 5 average rating, 13 reviews

Full Home Near Lake and Parks

You'll love this cozy home in a peaceful neighborhood with convenient access to parks, lakes, and local businesses. Whiting is a peaceful suburb bordered by downtown Chicago, Hammond, and Lake Michigan. You'll be within walking distance of several local parks and businesses, including a grocery store, as well as within easy driving or transport distance of several more parks and lakes, local attractions such as Horseshoe Hammond, and convenient access to Chicago by car or by train.

Dec 8 – 15

G$22,941 GYD per night

Guest favorite

Home in Chicago

4.98 out of 5 average rating, 66 reviews

Opulent 3bdr2bth Old Town Luxury + Parking prmts

Luxurious home in the heart of Historic Old town triangle. Fantastic location! Steps to restaurants, shops, Lincoln park Zoo, Lake Michigan, Brown line. Pristine craftsmanship throughout, with no expenses spared. Sleeps 4 people. Internet speed 1G. 3 smart TVs. Essential baby gear. Key-less self-check-in. Bicycles with locks for the guests to explore the city. Complimentary guest parking permits. Private chef is available upon request This home is perfect for business and pleasure!

Apr 13 – 20

G$152,834 GYD per night

Guest favorite

Home in Chicago

4.92 out of 5 average rating, 111 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!

Oct 15 – 22

G$72,745 GYD per night

Guest favorite

Home in Carol Stream

4.9 out of 5 average rating, 89 reviews

LAKE HOUSE HotTub/Kayak/Billiards/Pets/Fenced Yard

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)

Apr 2 – 9

G$43,366 GYD per night

Superhost

Home in Chicago

4.85 out of 5 average rating, 115 reviews

Huge Home * Yard * Parking * Best Location

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, and nightlife; 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, pets welcome - what else can you possibly need? Space is expandable from a smaller family to a group of 22.

Dec 18 – 25

G$176,038 GYD per night

Guest favorite

Home in Chicago

4.83 out of 5 average rating, 138 reviews

Historic Old Town, Fabulous 4 Bedroom Home

Lovely Historic 4 Bedroom, 3 bathroom home in Old Town, walking distance of restaurants, boutiques, coffee shops, the lake front and excellent public transportation. 2nd Fl. Master Bedroom has a King size bed and Twin plus private bath with bathtub, walk in shower, w/d; 2nd Fl. two room "suite" with a Queen size bed in each room and private bathroom. 1st Fl. bedroom with Queen bed and private bathroom. Off Street Parking and Private Deck!

Jan 20 – 27

G$75,176 GYD per night

Guest favorite

Home in Evanston

4.88 out of 5 average rating, 24 reviews

Sleepy sanctuary

A spacious, modern and comfortable 2 bedroom, 1 bathroom flat situated in the quiet and relaxing Evanston neighborhood, Kingsley. This corner property comfortably sleeps up to 6 so whether you and your sweetheart need a change of scenery or the family wants a getaway spot close to Lake Michigan beaches, we can accommodate a variety of guest sizes. Includes a laundry room, garage parking for one vehicle, two work spaces, and large backyard.

Jul 17 – 24

G$63,616 GYD per night

Superhost

Home in Chicago

4.87 out of 5 average rating, 15 reviews

Hot Tub Logan Family Designer Home

Enjoy a beautiful family home designed by one of NYC's top designers -- with abundant art, lots of space for kids, and a hot tub! Freshly redesigned, this is between Wicker Park and Logan Square, a perfect location for family and just a few minutes from downtown Chicago. Luxury linens, bedding, and touches abound. Explore excellent restaurants within walking distance, and a dedicated work desk, monitor, and playroom.

May 20 – 27

G$49,119 GYD per night

Superhost

Home in Des Plaines

4.83 out of 5 average rating, 167 reviews

Exotic House - Few minutes from O'Hare and Chicago

Located in the heart of Des Plaines and close to Chicago, not only is the house comfortable but it is also convenient due to the accessibility to various locations including O’Hare International Airport, Downtown Chicago, I-90 and I-294 Expressways, Rivers Casino, Allstate Arena, Fashion Outlets of Chicago, a chain of restaurants within 2-mile radius, Des Plaines Metra Station, Lake Park and Lake Opeka, etc.

Jan 19 – 26

G$45,434 GYD per night