Holiday rentals in Chicago

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Top-rated holiday rentals in Chicago

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Top guest favourite
A panoramic view captures a serene lakefront scene with sandy beach and calm waters. Colorful umbrellas shade outdoor seating arrangements near the water's edge, while paddle boards can be seen on the lake. Lush greenery surrounds the landscape, offering a tranquil retreat.
Guest suite in Waterloo
4.98 out of 5 average rating, 109 reviews

Lake Life (Something For All Ages & Seasons)

Beautiful private lower level, walk-out lake front in a quiet neighborhood. Spacious living quarters. Fireplace, full kitchen, bar, dining area, big screen TV. Bedroom has a queen bed. 2nd TV area has a queen Murphy bed. Bathroom has 2 sinks & a shower. Laundry room has a washer/dryer. Outdoor space includes a covered patio & hot tub, outdoor kitchen with chef's grill, refrigerator & fire pit. Kayaks, paddle boards, 2-person canoe, floats & fishing poles are available. Event Fee varies.

Guest favourite
A covered patio area features wooden posts supporting a slatted roof. Comfortable seating is arranged around a wooden table. A view of the lush green lawn leads to a wooded area beyond, providing a sense of privacy and connection to nature.
Guest suite in Omaha
4.89 out of 5 average rating, 158 reviews

Private Suite with Nature Views-Full Washer/Dryer

Backing to a wooded creek this home away from home is sure to be the relaxing place you are waiting for. This is a separate entrance lower level walkout apartment complete with kitchen, laundry, spacious bedroom, and 3/4 bath. Amenities include fiber gigabit high speed internet, smart TV (w/ Netflix), coffee bar able to brew ground coffee or K Cups, and dedicated off street driveway parking for two vehicles parked tandem. Please reach out if you have special requests or accommodations in mind?

Guest favourite
An open living area showcases a dark gray sofa and a comfortable recliner. A blue throw blanket is draped over the ottoman. A wall-mounted TV is positioned across from the seating, while windows allow natural light to fill the space.
Guest suite in Benson
4.93 out of 5 average rating, 148 reviews

Comfortable, Convenient, Private Basement!

You will be close to everything when you stay at this centrally-located place. Enjoy the privacy of having the basement to yourself! I have a 1 Bedroom 1 Bathroom fully finished basement. The bedroom has a King Sized bed. With a Twin XL bed in the living area! You will have a convenient private entrance/exit through the walk out basement. As well as your own driveway on the property. The living area is open, comfortable, and provides a 43' Smart TV with all the common streaming services.

Guest favourite
The living area features a warm, orange sofa facing a dark, low coffee table. A large Smart TV rests on a modern console across from the seating. Natural light filters through the double glass doors leading to a small balcony. Wooden floors add to the inviting atmosphere.
Flat in Omaha
4.8 out of 5 average rating, 56 reviews

Charming Dundee Fairview Apartment #9

Discover an inviting 1B/1B apartment nestled in the historic Dundee neighborhood of Omaha, within the iconic Fairview apartments designed by Henry Frankfurt in 1917. This inviting residence provides a central location with a beautifully updated interior and an outdoor balcony with courtyard views. You are a short walk from Dundee's finest restaurants and shops, 1.5 miles to the University of Nebraska Medical Center & 2.1 miles to Creighton University Medical Center. Come enjoy this space!

Top guest favourite
A two-story home is framed by lush green trees and shrubbery. The exterior features a mix of dark siding and a steep roof. An inviting pathway leads to the front porch, where soft lighting highlights the entrance. A well-maintained lawn enhances the curb appeal.
Guest suite in Omaha
4.9 out of 5 average rating, 107 reviews

Private Space, Walk-Out Basement of suburban home.

Our cozy, quiet, home backs to walking trail, creek & prairie. Easy access to interstate, restaurants & shopping. You have private access to our walk-out basement w/bedroom, living room, bathroom, and kitchenette, + board games, books, ping pong, our backyard and a nearby park. The bedroom has a Cal King bed & dark, cool sleeping. The family room includes two twin beds and a twin mattress on floor, plus our large comfy sofa and floor to ceiling windows showcasing our green space.

Guest favourite
A living area features a teal sofa with a yellow accent pillow, complemented by a tan lounge chair. A rectangular white coffee table occupies the center, placed on a patterned area rug. Light-colored curtains frame the window, and two bedside tables are positioned beside the sofa.
Home in Aksarben - Elmwood Park
4.75 out of 5 average rating, 149 reviews

Colorful Mid-Mod in Aksarben - 1 Mile from UNO!

-Triplex -Located in the Historical Aksarben neighborhood, just a few Blocks from Baxter Arena, Aksarben Village, University of Nebraska at Omaha, and Creighton University Medical Center (Bergan Mercy)! -Short 5-10min Uber/Lyft to Midtown, Blackstone and Downtown! -Professionally Decorated -WiFi -Roku Smart TV with Netflix and Sling TV access for streaming channels -Secured Coded Entry -Fully equipped kitchen for cooking w/ gas range -Limited on-site parking/no oversized vehicles

Top guest favourite
A cozy room features a spacious bed with a striped comforter and decorative pillows. A comfortable couch sits beside a bedside table and lamp, creating a welcoming area. A dresser is positioned against the wall, and soft lighting gives the space a warm feel.
Flat in Papillion
4.95 out of 5 average rating, 341 reviews

Coastal Retreat Getaway, Secluded, Off 370/I-80

Step into a private and cozy space. Relax watching TV in bed or on the couch. This place is part of our walk out basement, so you may hear day to day living upstairs. For your safety there is a Ring camera installed at the entrance and will light up the entryway when it’s dark. Parking is on the well lit public street. Easily walk up our dedicated Airbnb sidewalk, no steps, walk around to the back of the house. You’ll be in a serene space that makes you feel right at home.

Superhost
Guest suite in Omaha
4.79 out of 5 average rating, 228 reviews

Nestled in Nature

A mother-in-law suite perfect for individuals to families looking to stay in the prestigious Millard area. We are steps away from gorgeous Lake Zorinsky, golf courses, shopping, and other amenities. You can expect a friendly neighborhood, a full kitchen, gas fireplace, and natural light! Our shared backyard has a large fire pit, outdoor dining, and the gorgeous NE sunset. Lastly, check in is 6p and check out is 10a. *Please expect some noise from the main residence, above*

Guest favourite
A spacious modern home is displayed at dusk, with a well-defined driveway leading to a symmetrical facade that features two garage doors. The entrance is illuminated, highlighting the welcoming atmosphere. Dry grass surrounds the structure, offering a contrast to the warm hues of the setting sky.
Home in Omaha
4.92 out of 5 average rating, 25 reviews

Spacious Retreat in West Omaha 2 King 3 Queen Beds

Experience the best of Omaha from this spacious West Omaha retreat! This beautifully designed home features 5 bedrooms along with 3 FULL bathrooms and driveway parking. Located in a prime area, you're close to top dining, shopping, and entertainment, with easy access to all of Omaha. Perfect for families, business travelers, or groups looking to explore the city in comfort. Enjoy a stylish and fully equipped stay for a memorable visit!

Top guest favourite
Home in Omaha
4.96 out of 5 average rating, 23 reviews

Your Home Away from Home

Experience comfort, convenience, and style in this beautifully maintained home perfect for families, couples, or business travelers. Located in a quiet, safe neighborhood, this fully furnished space offers everything you need for a relaxing stay — spacious bedrooms, a fully equipped kitchen, high-speed Wi-Fi, smart TVs, and cozy living areas.Freshly painted and new carpet installed.

Top guest favourite
A spacious living area showcases a large, L-shaped sectional sofa in a rich brown hue. A wooden coffee table is centered on a textured area rug, with light streaming in through multiple windows. A television and entertainment unit complement the cozy space.
Home in Elkhorn
4.98 out of 5 average rating, 124 reviews

Private Basement Unit in West Omaha

Unwind and relax in our contemporary and spacious basement unit located in the suburbs of Omaha. The home is located in the Grove neighborhood, which is very safe and has a park, splash pad, and walking paths. The neighborhood is minutes from Village Pointe shopping area, twenty minutes from Old Market and the downtown area, and half an hour from the airport.

Top guest favourite
The exterior of a two-story villa features a light blue facade with white accents. A large tree with pinkish leaves stands nearby, and a driveway leads to a garage. The front entrance is framed by a small set of steps and a welcoming porch.
Home in Omaha
4.93 out of 5 average rating, 117 reviews

2 bedroom villa with garage in quiet neighborhood

2 bedroom villa in a popular SW Omaha neighborhood. Near Village Point and lakeside shopping areas. Also close to many dining venues, movies, hospitals and more. 2 large bedrooms and a pull out couch in the lower level. Garage available for parking. Patio is open to the common area . Close to walking paths and park. Fully furnished with all necessities.

Popular amenities for Chicago holiday rentals

  1. Airbnb
  2. United States
  3. Nebraska
  4. Douglas County
  5. Chicago