Holiday rentals in Diversey Harbor

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Top-rated holiday rentals in Diversey Harbor

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

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Top guest favourite
A spacious living area showcases a comfortable L-shaped leather sofa adorned with decorative pillows. A glass coffee table is positioned on an elegant area rug, while framed art pieces decorate the walls. A floor lamp provides soft lighting next to a small side table with a decorative plant.
Townhouse in Chicago
4.98 out of 5 average rating, 323 reviews

Beautiful Lincoln Park/ De Paul Complimentary Parking Permit

Located in the heart of Lincoln Park's Armitage/Halsted shopping district, one of Chicago's most desirable and walkable neighborhoods, steps from boutiques, cafés and public transit are all within a short walk. This is an urban, pedestrian friendly neighborhood where many visitors choose to explore on foot. Complimentary daily parking permits included. Please note that the apartment does not have an in-unit washer/dryer. For longer stays, laundry credit is provided for wash and fold service.

Top guest favourite
A spacious living area features a red sofa, a coffee table, and a flat-screen TV mounted on a brick wall. Large windows allow natural light to fill the space. Decorative plants are positioned near the windows, accentuating the room's inviting atmosphere.
Apartment in Chicago
4.99 out of 5 average rating, 312 reviews

Pets OK | Walk Score 95 | Desk | 1,750ft² |W/D

• 1,750ft² / 162m² . My home is on the first floor of a four flat Itallian Brick Building . You have 1 flight of stairs to climb to enter. • Walk Score 95 (walk to cafes, bars, eating, nightlife, etc.) • Biker's paradise • Fully equipped + stocked kitchen • Extremely safe neighborhood • Free street parking with pass included • in Unit Washer + Dryer ➠ 5 min walk to the Lincoln Park ➠ 10 min drive to Downtown Chicago ➠ 30 min drive to O'Hare Chicago Airport Note: fireplace is not operational.

Guest favourite
Flat in Chicago
4.78 out of 5 average rating, 276 reviews

Rare 1BR Lincoln Park Apt, close to everything!

Historical charm with modern updates in this 1 Bedroom Lincoln Park Condo. This is the perfect place to stay while you're in Chicago with it being steps away from Chicago's largest park, one of the country's oldest free zoos, nationally acclaimed dining, lakefront trails, museums, DePaul University and more. While you're at home, relax in the cozy living room, cook dinner in the full and updated kitchen, rinse off with the rainfall shower head, or get some rest on the queen bed in the bedroom.

Superhost
A spacious studio presents a comfortable living area with a dark sofa and a coffee table on a decorative rug. The dining area features a table with four chairs. Large windows brighten the space, while exposed wooden beams add character to the ceiling.
Flat in Chicago
4.8 out of 5 average rating, 182 reviews

Spacious Studio in Prime Location

Enjoy all Chicago has to offer from this recently renovated studio in Lincoln Park - one of Chicago's most desirable neighborhoods. Steps away from great dining and nightlife, this unit has a prime location. To get downtown, or really anywhere on the North Side, the Brown Line and various bus lines are within walking distance. Cleanliness is taken very seriously here. You will also find a fully equipped kitchen, quality sheets, and premium toiletries. The perfect garden unit for your trip!

Guest favourite
Flat in Chicago
4.9 out of 5 average rating, 42 reviews

Cozy & Stylish Lincoln Park Gem

Located on the 2nd floor of a classic Chicago greystone, steps from the best of Lincoln Park. A short walk east brings you to North Pond and the lakefront, while Clark Street around the corner offers endless spots for dining, coffee, and shopping. The home has everything you need for a comfortable, convenient stay. Your hosts are hospitality industry veterans, so you can expect both professional care and the warmth of a cozy home base. We look forward to welcoming you to our home and city!

Top guest favourite
Townhouse in Chicago
4.96 out of 5 average rating, 123 reviews

Hidden Gem - 3 Story House & Pet Friendly!

Cozy & entertaining family -pet friendly property in the heart of Chicago - Lincoln Park. This Smart triplex has a fully-equipped kitchen. Large patio w/ sunset views. 3 bedrooms & 2.5 bathrooms. A Foosball table, 82' TV & BAR to enjoy a night in. This property is perfect to book w/ family or friends. Its spacious yet set up the right way to entertain in one floor, cook in another & sleep without having to deal with noise. Pets: Certain restrictions may apply. It is $35/night per pet

Guest favourite
The spacious bedroom features a large bed dressed in crisp white linens, framed by soft side tables with gold accents. A piece of abstract artwork adorns the wall above the bed, and natural light enters through a large window with unobstructed views.
Flat in Chicago
4.74 out of 5 average rating, 1,357 reviews

Kasa | Spectacular City Views | Chicago

When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

Guest favourite
Flat in Chicago
5 out of 5 average rating, 8 reviews

Modern& Bright 2BR | Near Downtown & CTA

Book with confidence — highly rated stay with consistent 5-star guest experiences! Located on N Seminary Ave in a desirable Lincoln Park / DePaul area Fresh, modern design, comfortable bedrooms, and a bright living space Ideal for families, large groups, couples, students, business travelers, long-term stays, and remote workers Surrounded by cafes, restaurants, and neighborhood shops Easy to find free street parking without permit in walking distance Near CTA Safe, walkable area

Top guest favourite
A cozy studio space features a sofa with blue cushions, complemented by a light wooden table and colorful accent wall. Natural light filters through the window, casting soft illumination. A television is positioned on a ledge, with a decorative statue nearby.
Flat in Chicago
4.84 out of 5 average rating, 341 reviews

Cozy Lincoln Park Studio - Steps to Zoo!

This cozy studio in the heart of Lincoln Park is just steps away from some of the best experiences that Chicago has to offer! Just a block from the Lincoln Park Zoo and near the great restaurants and bars of the neighborhood, there's something here for everyone. See a show at the world-famous Second City, take a quick ride up Clark St to see the Cubs play at historic Wrigley Field, or just stay in and relax, there's no wrong way to spend your time in the Windy City!

Top guest favourite
A stylish living space is highlighted by a brown leather sofa and a large area rug, with natural light streaming through the window. The modern kitchen is equipped with sleek black cabinetry and stainless steel appliances. Potted plants add a touch of greenery to the setting.
Home in Chicago
4.96 out of 5 average rating, 288 reviews

Division St Designer Home In Heart of Wicker Park

Stay in the best location in the heart of the East Village/Wicker Park neighborhoods! Located on a quiet tree-lined street, you’ll be only steps to the cafes, restaurants, bars, and shops that flank trendy Division Street; a short walk to the vibrant Chicago Ave and Milwaukee Ave restaurant & retail corridors. Just off the Division Blue Line “L” stop, we’re just a quick train ride to both the Downtown Loop (8 minutes) and O’Hare International Airport (35 minutes).

Guest favourite
Flat in Chicago
4.98 out of 5 average rating, 206 reviews

Elegant Suite in Gold Coast

Steps away from the Magnificent Mile, and the high-end boutiques of Oak and Rush Street, this generous one-bedroom apartment is perfectly situated in the middle of the action for your Chicago adventure. ***Please note that from March until the end of September 2026, there will be construction on the upper floors of the building that may cause noise during the daytime hours. Construction will not be happening on the weekends.***

Superhost
Flat in Chicago
4.86 out of 5 average rating, 117 reviews

LIVN West Loop Chicago Queen Studio Apartment

Experience modern city living at LIVN West Loop Chicago, a stylish loft-style apartment studio at 555 W Jackson Blvd in one of the city’s most connected neighborhoods. This newly renovated studio features a full kitchen, in-unit washer and dryer, and clean, modern interiors. Walk to Union Station and Willis Tower. You are minutes from top dining, offices, and transit, ideal for business trips, weekend stays, or longer visits.

Popular amenities for Diversey Harbor holiday rentals

  1. Airbnb
  2. United States
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  5. Chicago
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