Holiday houses in Near North Side

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Top-rated holiday rentals in Near North Side

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

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Superhost
Apartment in Old Town
5 out of 5 average rating, 6 reviews

Oldtown Stylish cute studio Near Gold Coast

Welcome to our stylish studio unit nestled in the heart of the city's charming old town area! This cozy space is perfect for solo travelers or couples seeking a comfortable retreat. The studio boasts a spacious bathroom, providing ample room for relaxation after a day of exploring.With its central location, you'll have easy access to the city's vibrant attractions, trendy cafes, and historic landmarks. Our studio unit offers the perfect blend of convenience and comfort for your stay in the city.

Guest favourite
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 Gold Coast
4.86 out of 5 average rating, 205 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!

Top Guest favourite
Private room in Lake View
4.95 out of 5 average rating, 133 reviews

Fantastic Location / Private Room

Enjoy easy access to everything from this perfectly located home base. Walking distance to Wrigley Field, The Vic, The Briar Street Theater (Blue Man Group), some of the cities best restaurants, bars and coffee shops, Advocate Illinois Masonic Medical Center, The CTA’s Red Line which takes you right downtown to the Loop, Depaul, Chinatown and a host full of other Chicago destinations. There’s really no need for a taxi or Uber with so much that is walkable or accessible from the red line.

Superhost
Private room in Chicago
4.82 out of 5 average rating, 532 reviews

Florence Room - 3min to CTA, Free Parking, Roomy

The Florence room is one of three rooms in the grotto. The room has a king size bed and full size sofa sleeper for a maximum guest count of 4. You will have access to the kitchen for the microwave, toaster, and stove, along with free Keurig coffee. There are multiple common areas on the 1st, 2nd, and 3rd floors including Dining, Living, TV, and Recreation rooms.There is a private mini fridge in your room for food storage. The house is one block from the Kedzie Green line rail station.

Top Guest favourite
Private room in South Loop
5 out of 5 average rating, 142 reviews

Urban Oasis Pilsen - guest room in townhouse

Experience the charm of Pilsen, one of Chicago's trendiest neighborhoods. Your private bedroom features a queen-size bed and an en-suite bathroom with a tub/shower. The room includes a small desk, ample storage space, and a TV with streaming services. Triple-paned windows provide plenty of natural light while minimizing noise from the nearby I-90/94 freeway. The room is located on the third floor (40 steps)! The second floor offers access to the kitchen, living room, TV den, and balcony.

Top Guest favourite
A spacious living area is presented with wood flooring and modern furnishings. A circular black leather sectional sofa is centered around a glass coffee table, complemented by an area rug featuring orange, black, and red patterns. A spiral staircase leads to an upper level, while large windows illuminate the space.
Private room in Chicago
4.94 out of 5 average rating, 181 reviews

Cozy Private Room in a unique Chicago Penthouse

Our three bedroom Penthouse apartment has a cozy guest room with detached private bathroom. It fits two and is centrally located on a quiet street near Du Paul University. Enjoy a gourmet kitchen, roof access and easy access to major subway lines, coffee shops, restaurants and movie theater are all in walking distance. You will share the apartment with us and our two cats. Your room is totally private and the bathroom is only used by you. The apartment is a walk up on the fourth floor.

Superhost
Apartment in Lincoln Park
4.61 out of 5 average rating, 66 reviews

Winter Escape• Modern 1BR • Walk to All

Prime Location: Lincoln Park Zoo, Lake Michigan, North Avenue Beach, top-rated local restaurants, cafés, and boutiques Spacious & Bright: Enjoy a large open living space with natural light Work-Friendly: Dedicated workspace and fast Wi-Fi, ideal for remote work or study Self Check-in w/ Secure Entry: Keypad code access Easy Transit: Close to CTA buses and trains for fast access to downtown, Wrigley Field, and more FREE to use washer/ dryer with detergents and cleaning supplies

Top Guest favourite
A spacious living area is highlighted by a comfortable gray sofa adorned with warm-toned pillows. A wooden coffee table with magazines rests in front. The walls are painted in a vibrant yellow, complemented by a rustic shelving unit and decorative accents around the room.
Private room in Lower West Side
4.91 out of 5 average rating, 483 reviews

Spacious & serene in hip spot. Sleeps 4.

Located in the heart of Pilsen, a vibrant neighborhood rich in Mexican arts/ culture, and an emerging hipsterville. Check out art gallery crawls, award winning restaurants and local taquerias. Thalia Hall (3 blocks away) w/ indie and major musicians. 7 mins via car to downtown or 2 blocks to train/bus. Mask wearing is optional. Guests are not required to wear masks. Chicago Registration #: R21000069179

Top Guest favourite
The bright living area features a blue sofa with decorative pillows, a wooden coffee table, and a desk chair facing a small workspace. Natural light enters through multiple windows, showcasing the hardwood flooring and modern decor elements, including a framed cityscape artwork.
Condo in Lake View
4.99 out of 5 average rating, 669 reviews

Urban Comfort in the Heart of Chicago

This is the PRIVATE first floor of our duplex condo, with your own entrance/exit, 75" flatscreen TV, central heat/air, and a newly remodeled en-suite bathroom. We are in the middle of Chicago's vibrant Northside while still having the benefit of coming home to a tree lined one lane residential street. Please contact us with any questions at all before you book your stay.

Superhost
Private room in Norwood Park
4.77 out of 5 average rating, 338 reviews

Chicago River Room, near Med Ctr

R+ My other listings can be found through my profile page. 7 minutes to O'Hare Airport See below for details. Highway entrance 1 block away, so you can easily drive anywhere. Walking distance to pharmacy, shopping mall (including grocery store), health club, train station, restaurants and a library. 0.6 miles to Harlem Blue Line. Prices are subject to change.

Top Guest favourite
A spacious living room features three large windows allowing natural light to fill the space. Comfortable seating includes a leather couch and an armchair. A television is mounted on the wall, and a decorative area rug lies beneath a wooden table set for dining.
Condo in Noble Square
4.97 out of 5 average rating, 854 reviews

Great location. Free parking.

Great location in Chicago's Wicker Park/Bucktown community. Fully furnished living room, bedroom with queen bed and bathroom. Internet, central heating/ac, small refrigerator, microwave, cable TV, dvd/Blu-ray, coffee maker. Small safe. Private free parking. One block from blue line (Division). From O’Hare via train – 35 min. 10 min to the city via blue line.

Top Guest favourite
A welcoming living room features a large wooden table surrounded by plants and comfortable seating. Natural light floods the space through expansive windows, enhancing the earthy tones of the decor. A cozy sofa and a vintage armchair create an inviting atmosphere for relaxation.
Private room in Hyde Park
4.96 out of 5 average rating, 526 reviews

Private room w/bath in urban canopy

Private bedroom w/attached private bath in a gorgeous 3-bedroom/2-bath apt on the only curvy street in Hyde Park. Common entrance and living spaces, shared with an artist who uses two bedrooms - one as studio. Enjoy the lush light-infused top floor of a turn-of-the-century urban tree house.

Popular amenities for Near North Side holiday rentals

When is the best time to visit Near North Side?

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Avg. price$278 NZD$283 NZD$303 NZD$343 NZD$442 NZD$509 NZD$478 NZD$456 NZD$401 NZD$367 NZD$353 NZD$307 NZD
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Quick stats about holiday rentals in Near North Side

  • Total holiday rentals

    Explore 1,670 holiday rentals in Near North Side

  • Nightly prices starting at

    Near North Side holiday rentals start at $17 NZD per night before taxes and fees

  • Verified guest reviews

    Over 47,750 verified reviews to help you choose

  • Family-friendly holiday rentals

    590 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 910 rentals that welcome pets

  • Holiday rentals with a pool

    780 properties feature pools

  • Rentals with dedicated workspaces

    900 properties have a dedicated workspace

  • Wi-Fi availability

    1,650 of Near North Side holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Near North Side rentals

  • 4.7 Average rating

    Near North Side stays receive an average rating of 4.7 out of 5 from guests

  • Nearby attractions

    Near North Side's top spots, include 875 North Michigan Avenue, Chicago Riverwalk, and Museum of Contemporary Art Chicago

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