Lake house accommodation & holiday rentals in Chicago

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Top-rated lakehouse rentals in Chicago

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Guest favourite

Home in Chicago

4.87 out of 5 average rating, 117 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 favourite

Home in Evanston

5.0 out of 5 average rating, 59 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!

Superhost

Home in Whiting

4.83 out of 5 average rating, 123 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 Highland Park

4.93 out of 5 average rating, 40 reviews

Witness Sunrise Over Lake Michigan

Mesmerizing views of Lake Michigan from nearly every corner of this recently renovated Mid-Century Modern home. The house is walking distance from Ravinia Festival, downtown Ravinia Restaurants, and glorious Rosewood Beach; a healthy walk or short drive from Metra Train Stn. to Chicago and from the Chicago Botanical Gardens. Of course, guests can always choose instead to relax fireside, on the roof deck, or at the home’s private beach. Perfect for 4 guests, it accommodates 6. 2K, 2Q, 2.5 baths.

Guest favourite

Home in Gary

4.9 out of 5 average rating, 21 reviews

Spacious MCM beach house with private yard!

Welcome to Birdie's Beach Retreat! A beautiful mid-century modern house with all the updated amenities you could need. Only a 10 minute walk from the beautiful Lake Michigan beaches and a five minute drive to year-round hiking and outdoor activities at the Indiana Dunes National Park. Enjoy our 3 bedroom, 2 bathroom house with a large, private fenced-in backyard and deck. Beautiful indoor and outdoor space makes this the perfect getaway. House-trained dogs welcome! Sorry no cats (allergies).

Guest favourite

Home in Barrington

5.0 out of 5 average rating, 28 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.

Superhost

Home in Gary

4.94 out of 5 average rating, 86 reviews

Sunset beach house

Super beach location ,3 bedroom , 2 bath house with amazing view of the lake, 6 person hot tub open Sep-Nov, Apr-Jun, beach access, 100 steps from water Bright, sunny, dining in a sun room with the view of the lake. First floor two large bedrooms, bathroom ,gourmet kitchen, large living room, gas fireplace, dining room. Lower level -large smart tv in family room with comfortable sofa , big bedroom, bathroom and washer/dryer , grill, fire pit Do not accept pets and ESP due to allergies

Guest favourite

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.

Guest favourite

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!

Superhost

Home in Chicago

4.85 out of 5 average rating, 116 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, 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.

Superhost

Home in Chicago

4.89 out of 5 average rating, 18 reviews

Hot Tub Logan Family Designer Home

Enjoy a beautiful family home on a quiet tree-lined street 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.

Guest favourite

Home in Chicago

4.82 out of 5 average rating, 139 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!