Lake house vacation rentals in Lake View

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Top-rated lake house rentals in Lake View

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Guest favorite

A stylish living area features a combination of striped and solid-color chairs, a plush area rug, and a modern coffee table. Large windows provide natural light, while a decorative fireplace adds to the cozy ambiance of the space.

Home in Lake View

4.88 out of 5 average rating, 143 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 favorite

A charming brick duplex is depicted, featuring a well-maintained front yard with green shrubs and stone steps leading to the main entrance. Two simple outdoor chairs provide a welcoming touch, while sunlight highlights the architectural details of the building.

Home in Evanston

4.97 out of 5 average rating, 37 reviews

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.

Guest favorite

Home in Near North Side

4.99 out of 5 average rating, 76 reviews

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.

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Home in Chicago

4.87 out of 5 average rating, 45 reviews

Executive Contemporary Duplex

Discover a newly remodeled, stylish, & spacious 2-bedroom garden home nestled in the historic Bronzeville neighborhood. This beautiful residence boasts enchanting décor and well-appointed living spaces that promise a memorable stay. Its minimalist charm and comfortable setup reflect a contemporary/modern aesthetic, making it an irresistible choice for guest. Just 6 mints from the downtown, 20 mints from Midway Airport, and 4 mints from McCormick Place & UOC, it's perfect for any length of stay.

Guest favorite

An open living area features a stone-finished fireplace and a large area rug. Two blue sofas, one with decorative cushions, frame the space. A wooden coffee table sits on the rug, with green plants enhancing the setting. Light flows in through nearby windows leading to the dining area.

Home in Old Town

4.87 out of 5 average rating, 145 reviews

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!

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Home in South Side

4.8 out of 5 average rating, 5 reviews

Bronzeville 42: Art & Hospitality Mins to Downtown

Bronzville 42 (B42) is a vibrant space where art meets hospitality! Featuring captivating artwork from the owner's collection, B42 is beautifully decorated and conveniently located just 12 minutes from Downtown and minutes to Hyde Park, the lakefront beach, and the upcoming Obama Presidential Center (opening spring 2026). Dining: - Table seats 6 - Kitchen seats 4 Accommodations: - Sleeps 8 Bedrooms: 1. BR1: King bed 2. BR2: 2 Twin beds 3. BR3: 2 Queen beds Bathrooms: 2 Full Bathrooms

Guest favorite

The exterior of the home is showcased, featuring a light-colored brick facade and large windows that invite natural light. Lush greenery and flowers adorn the front yard, providing a welcoming touch. A small fence and steps lead to the entrance, enhancing the home's charm.

Home in Old Town Triangle

4.98 out of 5 average rating, 86 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. Pet friendly This home is perfect for business and pleasure!! Event allowed with host approval.

Top guest favorite

A spacious living area is illuminated by natural light, featuring large windows that frame views of greenery outside. A modern sofa and armchair sit around a round coffee table, while a sleek fireplace adds warmth to the elegant decor.

Home in Gold Coast

5 out of 5 average rating, 42 reviews

Gold Coast Home|Rooftop |PoolTable |Parking |Views

Luxurious Gold Coast Townhome – Offers Indoor Games, Rooftop, Parking & More! Experience the best of Chicago in this stunning 4,000 sqft Gold Coast residence. Perfect for groups of up to 12, this home features 4 spacious bedrooms, 4.5 bathrooms, and a ceiling-length window with incredible views. Enjoy a variety of indoor games and make use of the convenient rooftop. Whether you're here for leisure or work, this property offers modern amenities and unforgettable comfort in the heart of City

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Home in Humboldt Park

4.89 out of 5 average rating, 63 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 and between Wicker Park and Logan Square, this is a perfect location for family and just a few minutes from downtown Chicago. Luxury linens, bedding, and touches abound. Explore the elevated 606 trail, excellent restaurants within walking distance, and a work desk, 4K monitor, and playroom. And secret beach!

Guest favorite

A sunny view of a street corner is visible, framed by a wrought-iron fence. Green trees line the streets, providing shade to the area. Nearby buildings exhibit a mix of architectural styles. Paved roads and parked cars contribute to a lively neighborhood ambiance.

Home in Lake View

4.9 out of 5 average rating, 158 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!

Guest favorite

The exterior of a charming two-story home is featured, surrounded by well-maintained landscaping. A pathway made of pavers leads to the front entrance, framed by vibrant green shrubs and trees. The house showcases a gabled roof with dormer windows and yellow front door.

Home in Skokie

4.87 out of 5 average rating, 99 reviews

Luxe-Haus of Love—The 1938 Cape Cod |Heated FLRS |

20 mins from popping downtown Chicago and tucked within one of the Northside’s finest tree-line streets—The Haus of Love: A modern wood burning fireplace, new hardwood floors, and a bright airy space greets you in this newly renovated Kosher inspired design Spacious Eat-In Kitchen w/ double everything. Separate Formal Dining. Wetbar. High End Quartz Countertops 3Bd 3.5Bath Master BD w/Heated Floors, 10-ft ceiling, skylights, and a huge 8-ft tub.

Guest favorite

Home in Old Town Triangle

4.99 out of 5 average rating, 70 reviews

Old Town Cosmopolitan Four Bedroom, Four Bath

Elegant 5 Bedroom, 4 Bath Home in the Historic Old Town Neighborhood of Chicago. Just north of the Gold Coast, walking distance to the Lake, Beach, Lincoln Park Zoo, Parks, DePaul University, the Chicago History Museum and Countless Restaurants, Coffee Shops and Boutiques. Excellent Public Transportation. Easy Parking. Posh yet comfortable, the home boosts a gorgeous gourmet kitchen which opens up to a sitting room.