Beachfront vacation rentals in Cook County

The two-story house is nestled among lush greenery, showcasing a two-tone exterior with a combination of light and dark colors. Large windows illuminate the front, complemented by a well-maintained lawn and selective landscaping. A garage is visible on the right side of the structure.

4.62 out of 5 average rating, 164 reviews

Miller Beach Dune House

In the summer sit on the screened 2nd floor front porch and watch the forest sway in the breeze. Only a 5 minute walk to the miles-long Lake Michigan beach. Hike in the dunes; walk to the local restaurants and bars on Shelby (6 blocks). 8 minutes to downtown Miller, 1 hour to Chicago by train or car; quiet neighborhood, resident-only parking. In winter, great wood fireplace and forest views from the second floor living area. Cottage is older but clean and comfortable. Wifi. Full kitchen.

The modern two-story house is surrounded by landscaped grounds, featuring a mix of wood and dark paneling. A spacious deck extends from the upper level, with seating and hanging planters. A pathway leads to the outdoor dining area, bordered by vibrant flower pots.

4.96 out of 5 average rating, 101 reviews

Steps from the beach and a mile from National Park

Perfect for family or friends to relax and enjoy Indiana’s Dunes National Park! The Holliday House is a 2022 custom built home with lake views and a beach path just STEPS from the front door! This 2000 sq ft open concept design features 3 bedrooms and 3 bathrooms, 16’ ceilings, open great room with beautiful indoor/outdoor kitchen, custom dining seating for 8, and loft hammock. Hosts live next door and are easily available if needed! Everything is on the 1st floor except for the 3rd bedroom.

4.98 out of 5 average rating, 112 reviews

An outdoor seating area features a cushioned sectional sofa and a wooden coffee table, overlooking a heated in-ground pool. Lounge chairs are positioned nearby, surrounded by trees, with a view of Lake Michigan in the background.

Guest suite in Gary

Beachfront- Lake Michigan-Hot Tub-Heated Pool

Lake Michigan - Beachfront w/Heated In-Ground Pool- Hot Tub - Indiana Dunes National Park - Private Basement Guest Suite - 2 Bedroom/2 Bathrooms - Beautifully Decorated This guest suite has everything you need for a comfy and relaxing stay. Enjoy the 3-person hot tub, perfect for unwinding after a day of adventure. In the summer months, enjoy the heated, in-ground pool. Hiking, beaches and so much more await—and less than an hour’s drive to Chicago. Heated Pool Open from Mid-May to Mid-Oct.

An open living space features vaulted wooden ceilings and large floor-to-ceiling windows, providing views of Lake Michigan. A cozy fireplace is situated against a stone wall, and a dining area is highlighted by a round table surrounded by four chairs.

5 out of 5 average rating, 22 reviews

Beachfront-Lake Michigan-Indiana Dunes-5BD/3BR

🌊 Stunning Lakefront Getaway in Miller Beach | Sleeps 10 | Indiana Dunes National Park Welcome to your dream lakefront escape! This thoughtfully curated mid-century modern home is nestled within the boundaries of Indiana Dunes National Park, offering breathtaking views of Lake Michigan, the relaxing sound of the waves, and a peaceful setting that’s ideal for making lasting family memories. 🛏️ 5 Bedrooms | 7 Beds | Sleeps 10 🛁 3 Full Bathrooms 🧺 Washer/Dryer 🏖️ Access to A Secluded Beach

Guest favorite

The townhouse stands elegantly among lush greenery, featuring a classic facade with black-framed windows and a welcoming entrance. A wrought-iron fence complements the landscaped front area, while a tree provides shade along the sidewalk.

Townhouse in Chicago

4.84 out of 5 average rating, 231 reviews

Historic luxury townhouse on Chicago's Gold Coast

Welcome to our stunning Townhouse located in the lavish Gold Coast of Chicago—one of the most sought-after locations in the city! Located on one of Chicago’s famous streets, you’ll be a 5-minute walk from the historic Gold Coast beach and intimate views of Lake Michigan. The property is also within walking distance of the subway, where you can connect to the L trains, and the Magnificent Mile. It is the perfect place to stay for adventurous travellers and those who fancy a beach in the City!

4.92 out of 5 average rating, 274 reviews

The historic stone façade of the building features intricate architectural details, with large arched windows and a welcoming entrance. Flower pots are displayed on the balcony, and a wrought iron fence surrounds the property, adding to the charm of the exterior.

Apartment in Chicago

Stone Mansion Sleeps 10-20 Free parking & TV

Giant, 4 bedroom, 2,300 square feet apartment on 2nd floor, near Red Line Train, bars, cafe's, shopping, restaurants, Lakefront and everything else Chicago has to offer. Large living room with bar area, TV and fridge for socializing before hitting the town. Dining room has a large table and 8 chairs. 4 bedrooms with 2 private rooms with king beds and one with a double bed. 4 futons for in the living room for extra sleeping space two (2) parking spots in the west facing garage on premises.

Guest favorite

A spacious living area features a large sectional sofa facing a media unit with a TV, accompanied by a coffee table. A dining table with four chairs sits nearby. Floor-to-ceiling windows provide bright natural light and a view of adjacent buildings.

Condo in Chicago

4.86 out of 5 average rating, 207 reviews

2BD/2BA MAG MILE MASTERPIECE (+Rooftop)

Welcome! Guests love our home because: - You're SECONDS from the LAKE and MAGNIFICENT MILE - You're steps away from the famous Drake Hotel and Oak Street Beach. - Walk to every popular attraction that makes Chicago so great! - Newly remodeled interior with an open floor plan layout - Tranquil rooftop overlooking the Lake - Fast WIFI - Super comfy beds! - Custom chef kitchen - Located on a quiet street - Lake Michigan view from our floor-to-ceiling windows We look forward to hosting you!

Home in Chicago

New place to stay

Historic Gilded Age Gold Coast Mansion w/ Deck

RENT WITH CONFIDENCE FROM SUPERHOST WITH OVER 800 FIVE STAR REVIEWS One-of-a-kind opportunity to rent a historic Gilded Age Chicago Gold Coast mansion. All modern amenities meet Romanesque Revival style at this huge 5-bedroom Graystone. Steps away from Rush St restaurants, Division St nightlife, Oak Street Beach, and Michigan Avenue shopping. Enjoy central air & heat, 3 fireplaces, a fully stocked kitchen, balcony and an attached garage. Pets are welcome. What else could you possibly need?

4 out of 5 average rating, 3 reviews

Apartment in Chicago

A Sunny, Well-Kept & Comfy Studio in Gold Coast

Stay in a cozy, clean, and bright Gold Coast studio right in Chicago’s most iconic neighborhood. Rest comfortably in the well-furnished space, complete with a seating area and a full kitchen for convenient cooking. The bathroom is stocked with fresh towels and essential toiletries. With Oak Street Beach, Michigan Avenue shops, dining, nightlife, and public transit only moments away, getting around is effortless. Perfect whether you’re here for a quick trip or an extended visit.

4.66 out of 5 average rating, 56 reviews

A grand piano occupies the foreground, showcasing a polished surface that reflects light. Behind it, a spacious area is visible with a row of blue chairs and a ceiling adorned with modern chandeliers, highlighting the open and elegant design of the indoor space.

Villa in Chicago

Rooftop | Villa | Events

Gorgeous designer space, a mini Villa but large throughout making it light, bright, airy with feelings of calm and tranquility. Party Backyard/Rooftop Indoor features Luminaire Chandeliers, 10 feet ceilings, Grand Piano, Music Box etc. Huge backyard offer spaces to entertain. You’re booking a private residence: Three levels of home exclusive to your guests/party. Guest can view cameras of all entrances; Roof deck, Front, Back & Alley via Monitor (HDMI-1) 24/7 record.

4.96 out of 5 average rating, 408 reviews

An open studio space features a black leather sofa alongside a wooden coffee table on a textured rug. Colorful wall art adds vibrancy, with a light fixture illuminating the area. A chair with a unique design offers additional seating, enhancing the contemporary aesthetic.

Guest suite in Gary

Miller Mermaid Suite-100 yds from the beach!

100 yds from the beach, the cozy MERMAID SUITE is best for a young family or 2-3 adult friends. This artsy basement/studio includes: private entrance, kitchenette, unique art, cozy reading/sleeping nook. There is one small window with no lake view but you can see the lake from the upstairs deck. BBQ on the grill. Visit local restaurants, shops & galleries. Hike wooded trails & swim by sandy, dune-grass beaches. . House-trained dogs welcome! Sorry no cats (allergies)

Guest favorite

An in-ground pool is surrounded by lush greenery and outdoor seating areas. Sun loungers are positioned near the clear blue water, and a shaded patio area features red umbrellas. The pool area is well-maintained, inviting relaxation after a day by the beach.