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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Guest favourite

Guest house in Evanston

4.94 out of 5 average rating, 117 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

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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.

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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 favourite

Flat in Chicago

4.92 out of 5 average rating, 226 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 favourite

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 favourite

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!

Private room in Chicago

4.76 out of 5 average rating, 167 reviews

Basic accomodation equipped for short terms stays.

I am renting out my extra bedroom in my 2 bed condo for 1 guest only. Guests have access to their bedroom and bathroom only. No kitchen or living room access. My space is not luxury, but it's sanitized and clean, the neighborhood is cute/safe where you can feel calm/ peaceful. I have a lovely park across the street you can lounge. I am in an area where there are good restaurants within walking distance. Apartment 1W edit: Do not book my place for someone else under your profile.

Villa in Chicago

4.63 out of 5 average rating, 51 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 favourite

Flat in Chicago

4.96 out of 5 average rating, 57 reviews

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

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.

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Flat 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!

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.