Beachfront holiday 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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Top guest favourite

Guest house in Evanston

4.94 out of 5 average rating, 122 reviews

Historic Coach House in Evanston Near Beach & Town

Stay in the Coach House of this exquisitely restored Historic Landmark Manor House, one block to Lake Michigan's beaches and close to town and NU. Enjoy the entire coach house which is renovated and includes a large bedroom with king bed and desk, a sun-filled living room/dining room, a full bath with claw-foot soaking tub and shower and a kitchen with amenities. The space can be equipped with an air mattress for an extra guest. Also available is a 3rd floor guest suite in the main house . Extra

Top guest favourite

Flat in Chicago

5 out of 5 average rating, 14 reviews

Buena Vida Casa

Welcome to Buena Vida House. Step into a beautifully updated oasis where every detail has been thoughtfully designed to create a peaceful, stylish getaway. This all-new unit features fresh finishes, modern comforts, and a unique blend of beachy and boho vibes. Wake up just steps from the lakefront, ideal for morning jogs or simply soaking in the beauty of Chicago shoreline. This one-of-a-kind space offers comfort, charm, and convenience in one of Chicago’s most walkable and scenic neighborhoods

Superhost

Townhouse in Chicago

4.83 out of 5 average rating, 214 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!

Guest favourite

Flat in Chicago

4.92 out of 5 average rating, 246 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.

Superhost

Apartment in Chicago

4.87 out of 5 average rating, 197 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!

Guest favourite

Private room in Evanston

4.82 out of 5 average rating, 79 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!

Top guest favourite

Flat in Chicago

4.97 out of 5 average rating, 72 reviews

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

FREE GARAGE PARKING! Garage Clearance 6ft. 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.

Flat in Chicago

4.54 out of 5 average rating, 118 reviews

Entire APT in heart of Lincoln Park&Lake and beach

This home is located In the heart of Lincoln Park near Old Town Triangle and near the beach in the core of Chicago. Ideal people who want to stay in the vibrant beautiful city. Close to parks, beach, lake, subway station, shops, restaurants and night life! Entire one bedroom apartment with spacious (850 sqft) and beautiful interior design. As you can pick up the key from self check-in box, you can check in and out anytime. Check in time is 2pm and check out is 11am. R22000082349

Superhost

Villa in Chicago

4.64 out of 5 average rating, 53 reviews

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.

Superhost

Flat in Chicago

4.85 out of 5 average rating, 60 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!

Flat in Chicago

New place to stay

Sunny Lakeside Apartment in Rogers Park

Relax in this sunny, tranquil 1BR apartment just steps from Lake Michigan! Enjoy easy beach access, walk to local cafés and shops, or hop on the train—downtown is just 20–30 minutes away. Loyola University is a 15-minute walk, and Northwestern is a 15-minute drive. Bright, peaceful, and fully equipped, this cozy space is perfect for a weekend getaway, work trip, or campus visit. Feel at home by the lake in one of Chicago’s most vibrant neighborhoods!

Home in Chicago

4.85 out of 5 average rating, 33 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.