Lake house holiday rentals in Lake View

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.

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.

Amazing Location! Spacious Duplex Getaway

Welcome to your perfect getaway! This beautifully renovated duplex is ideally located, just steps away from charming coffee shops, local restaurants, and Lake Michigan. Only 2 blocks from Metra and CTA stops, you will have convenient access to downtown Chicago, Wrigley Field, Northwestern University and much more. With a free off-street parking spot, comfortable king-sized beds and fast wi-fi, whether you're here to explore or just relax, you'll love the convenience and comfort this home offers.

*New* Luxury Wrigley Penthouse, Free Parking

✨ NEW Guest Favorite in Chicago Wrigleyville! SPACIOUS 3BR, 2.5BA DUPLEX, UP TO 12 GUESTS w/ NEW FURNITURE, BEDS & GAME ROOM ✨ A standout stay in Chicago — nothing else like it! Just a 5-min walk to Chicago Red Line Station (10 mins to Downtown Chicago!) & only 5 mins to Wrigley Field. Walk to cafes, shops, parks & more. Includes FREE parking, fast Wi-Fi, foosball & arcade games. Perfect for friend groups, families, corporate housing, and digital nomads! A perfect score in the heart of Chicago!

Private Downtown Retreat with Rooftop Oasis

Welcome to your exclusive retreat in the heart of the city, where urban sophistication meets unparalleled comfort. Nestled in between Magnificent Mile and Gold Coast, this luxurious Airbnb offers a haven of style and tranquility amidst the hustle and bustle. The rooftop patio offers incredible views of the city skyline, with touches of lush greenery. The spacious living areas boast oversized windows that flood the space with natural light. Each bedroom is a sanctuary where luxury meets comfort.

Huge Downtown Gem *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!

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. Pet friendly This home is perfect for business and pleasure!! Event allowed with host approval.

Oakwood Beach Lake & SkylineViews+CuldeSac+Parking

Modern luxury awaits you in this Urban Oasis in North Kenwood/ McCormick area. New construction with all new finishes and stylish decor. Great natural light, free parking, views of Lake Michigan and the Chicago Skyline, nestled on a culdesac. Take advantage of countless attractions that the Windy City has to offer. A few minutes from Navy Pier, Downtown, White Sox Stadium, Museum Campus, University of Chicago, 31st Street and Oakwood Beach Perfect for photos and filming!

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!

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! License Pending.

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 with monitors, and large backyard.

Luxury Home - Pool Tbl/Bar/Patio

This unique place has a style all its own. Fully remodelled to wow you and your guest! Cozy, yet spacious environment for you and your friends to rest, cook, play pool by the bar or sit outside in the patio with a wood fire! You will be extremely close to downtown Chicago, O’Hare airport, Wrigley Field, many shopping attractions all while being in a safe neighborhood. Easy self checkin process!