Beachfront vacation rentals in North Side

Find and book unique beachfront homes on Airbnb

Top-rated beachfront rentals in North Side

Guests agree: these beachfront homes are highly rated for location, cleanliness, and more.

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Superhost

A historic manor house is seen adorned with lush greenery and beautiful landscaping. The structure features multiple balconies and large windows, highlighting the charm of its architectural design. A manicured lawn stretches in front, creating a serene setting.

Guest suite in Evanston

4.82 out of 5 average rating, 100 reviews

Historic Manor House Private Guest Suite Evanston

Stay in the Guest Suite of this exquisitely restored Historic Landmark Manor House, one block to Lake Michigan's beaches and close to town and NU. Enjoy the entire third floor, which includes 3 bedrooms, a private bath with claw-foot soaking tub and shower, private kitchen with full amenities, and the original ballroom which serves as a living and dining room. Air mattress for 1 extra guest. Available as separate rental, is a 2nd floor bedroom for 2 extra guests or a coach house which sleeps 2.

Superhost

A view from a second-floor porch showcases a mix of residential rooftops and lush green trees, creating a serene natural backdrop. The sky is partly cloudy, enhancing the tranquil ambiance. Brick buildings can be seen alongside the greenery.

Private room in Evanston

4.88 out of 5 average rating, 72 reviews

NU/Lake Evanston quiet/cozy semi private

SEMI private room divided from my bedroom by a half wall and nature tapestry: (photo from my room looking in.) NOT sound proof but visually private, with separate entrance and large desk with lovely window. Also a block from Whole Foods and the library. Four blocks from Davis street train station, Trader Joe’s, numerous restaurants, shops and landmarks very near. Bike, divvys available. Free breakfast. Room CANNOT be locked from the outside because it is against fire regulations, but all safe.

Guest favorite

Townhouse

4.84 out of 5 average rating, 199 reviews

Historic lux Townhouse on Chicago's Gold Coast

Welcome to our stunning Townhouse located in the luxurious Gold Coast of Chicago. Perhaps the BEST location in Chicago! Located on one of the desirable & famous streets in Chicago, this property is a 5 min walk from the Gold Coast beach where you will see Lake Michigan in all of its glory. Not to mention the proximity of this property to the subway and within walking distance of Magnificent Mile. It is the perfect place to stay for the adventurous and also those who fancy a beach in the City!

Guest favorite

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

4.92 out of 5 average rating, 227 reviews

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.

Top guest favorite

The spacious bedroom features a queen bed dressed in white bedding against a deep blue wall. Large windows with sheer curtains allow natural light, complementing the traditional furnishings, including a wooden dresser, a desk with a lamp, and a television.

Private room in Chicago

4.98 out of 5 average rating, 42 reviews

Sunny,Comfortable,CleanTop Location at Lake,Beach

Comfortable, large, sunny bedroom. Perfect for relaxation, work, study. Many amenities: wifi, desk, tv, coffee maker, small refrigerator. Private bathroom with shower/tub. Friendly hosts will welcome you. Fabulous location, fifteen minutes from downtown Chicago. Within 1/2 block of public transportation, Lake Michigan, beach, park, tennis courts. Six blocks to Loyola University. 3.5 miles to Northwestern U. Wonderful neighborhood, stores, restaurants, theaters, coffee shops, grocery.

Top guest favorite

A charming Tudor home is surrounded by a lush garden filled with vibrant greenery and colorful flowers. The front entrance features a distinctive design with a porch that invites guests in. Sunlight filters through the surrounding trees, enhancing the tranquil setting.

Private room in Evanston

4.84 out of 5 average rating, 68 reviews

1 Room for up to 3, Near NU & Old Orchard Mall

Close to fabulous shopping at Old Orchard. Avoid the traffic! Walk or jump on the bus for OO, NU. Can host 1 couple or up to 3 people in one room; 2nd room available for 2 additional guests. Charming art-filled Tudor home, beautiful garden setting near NU, lake, downtown Evanston. Large private room, queen bed + twin, updated bathroom. Free street parking. Perfect spot for visiting NU, many North Shore sights, local retirement communities. Easy access to trains to city. Great restaurants!

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

4.63 out of 5 average rating, 52 reviews

Rooftop | Villa | Parking

Meet up with group at this gorgeous designer space, a mini Villa but large throughout making it light, bright, airy with feelings of calm and tranquility. Indoor features Luminaire Chandeliers, 10 feet ceilings, Grand Piano, Music Box etc. Huge backyard offer spaces to entertain. You’re booking a private residence: 3 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

Guest favorite

A private patio provides a cozy seating area featuring a 3-seater sofa and two accent chairs. A round coffee table sits in the center, with the urban street view visible beyond the wrought iron railing.

Apartment in Chicago

4.96 out of 5 average rating, 57 reviews

Gold Coast Pristine 3BD|2BR| Patio |Parking| Views

FREE GARAGE PARKING! Step into luxury in this modern loft with 3 bedrooms, 2 bathrooms and a private patio with breathtaking views. Experience the feeling of being at home in a bright and spacious haven amidst Chicago's most sought-after neighborhood "Gold Coast" This centrally located gem is situated within walking distance of much of Chicago Downtown's exquisite dining, upscale boutiques, popular tourist destinations, and just a stone throw away from Oak Beach.

Superhost

A cozy living area features a brown sofa adorned with patterned cushions, paired with two armchairs. A round coffee table sits centrally, surrounded by natural light from windows. A large artwork of a roaring tiger dominates one wall, while a potted plant adds a touch of greenery.

Apartment in Chicago

4.82 out of 5 average rating, 51 reviews

Woodlawn Oasis

Welcome to Woodlawn Oasis! Come and enjoy the charm and warmth of this fully remodeled and furnished apartment with original artwork! Just 5 minutes from our beautiful Chicago lakefront, the prestiges University of Chicago, and soon to be Tiger Woods golf course and President Obama library. Also, 10 minutes from Chicago museums, Soldier Field (Chicago Bears), Guaranteed Rate Field (Chicago White Sox) and the fabulous night life of Downtown Chicago!

A charming gray two-story home features a welcoming yellow front door. The porch is adorned with potted flowers, and large windows allow natural light to enter. The surrounding landscape includes well-maintained shrubs, creating an inviting approach to the entrance.

Home in Chicago

4.84 out of 5 average rating, 32 reviews

Only Urban Beach House in Chicago

Why stay in a hotel or dorm when you can have your own house! The Urban Beach House of Rogers Park, Chicago’s only urban beach house, has 4 bedrooms, 3 full baths, and is loaded with features that make it the perfect place for vacationers, students, faculty, family and gatherings of all kinds. Steps from the sandy beaches of Lake Michigan, walking distance from dozens of restaurants and shops, and minutes from 3 train stations and a Divvy bike station.