Holiday rentals in Chicago

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Top-rated holiday rentals in Chicago

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

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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, 110 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, 159 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?

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.

Top guest favourite
A ranch-style home is depicted with a well-maintained lawn and shrubs. A two-car garage is visible on the left, and large windows provide natural light to the living areas. The clear blue sky enhances the inviting appearance of the welcoming exterior.
Home in Omaha
4.92 out of 5 average rating, 167 reviews

Inviting Place To Call Home For A While

This is a lovely home, in a very family oriented neighborhood. The rooms are all good sized. My home has been freshly painted. I have the carpet cleaned, and also top to bottom, thorough cleaning done on a regular basis. I am not in the airbnb business. Two of my children live in Nebraska, everyone else is in NJ. So we go back and forth. Our home is located in Western Omaha, a very quiet area, yet within 20/30 minutes of everything. Including the zoo, downtown, and the outlets.

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, 347 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, 230 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*

Top guest favourite
The exterior of a two-story house is depicted, featuring a light brown siding and a brown shingle roof. A concrete driveway leads to a garage, while steps invite entry to the front door. Lush greenery surrounds the home, enhancing the inviting appearance.
Home in Waterloo
4.9 out of 5 average rating, 101 reviews

Comfortable, 3-bedroom home on a quiet cul-de-sac

Welcome to a home away from home, conveniently located in the "backyard" of Omaha! All of our guests have full access to the entire home, located on a large corner lot in a quiet cul-de-sac. Less than 30 minutes from downtown (think Omaha Zoo, Century Link Center, etc.). Less than 20 minutes from I-80 and popular Omaha neighborhoods like Aksarben Village, and Midtown Crossing are only 15-20 minutes away. Only blocks away from some of the best restaurants around as well!

Guest favourite
A modern kitchen corner features light-colored cabinetry with dark knobs. A red coffee maker sits on the counter next to a decorative sign that reads 'rise & shine it's coffee time.' Stylish potted plants and colorful bowls add charm to the space.
Home in Gretna
4.95 out of 5 average rating, 180 reviews

Charming Gretna Bungalow Between Omaha and Lincoln

Relax with your family at this small-town home, 30 minutes between Omaha and Lincoln. Built in 1890, the house is full of charm and character, with unique built-ins and vintage art. Close to shopping, restaurants, coffee shops, hiking, and family-friendly activities: Vala’s Pumpkin Patch, Nebraska Crossing Outlet Mall, Strategic Air Command & Aerospace Museum, and Lee G. Simmons Wildlife Safari. Minutes to top-rated state parks and golf courses.

Top guest favourite
A spacious living area is filled with natural light from large windows. A teal sectional sofa is complemented by light-colored armchairs and a round coffee table. A textured area rug covers the hardwood floor, while a decorative plant and wall clock add subtle accents.
Home in Omaha
4.95 out of 5 average rating, 123 reviews

Light & Bright 4 bedroom Home in West Omaha

Cheerful family friendly 4 bedroom home in the heart of Southwest Omaha. Close to great restaurants and shopping. All Brand new furniture/decor and super comfy memory foam beds will have you basking in these boho modern vibes. 1 mile to Zorinsky Lake with beautiful walking trails and fishing. 2 miles to Legacy village with Lifetime Fitness & great food options. 5 miles to Village Pointe for many more shopping and dining options. You'll Love it!!

Superhost
A bright kitchen features white cabinetry and sparkling granite countertops. Stainless steel appliances, including a dishwasher and stove, are present. A window offers a view of the outdoors, and modern lighting fixtures provide illumination. Ample storage is available in the surrounding cabinets.
Home in Omaha
4.81 out of 5 average rating, 199 reviews

Family Home

Experience the ultimate comfort and relaxation in this charming four-bedroom, two-bath Airbnb nestled in the serene Millard area. This cozy retreat offers easy access to major streets and Interstate 80, making it an ideal choice for travelers. Sink into plush beds adorned with luxurious linens, providing a restful night's sleep. In the heart of the home, a fully equipped kitchen awaits, with top-of-the-line appliances and ample counter space.

Top guest favourite
A comfortable living area is shown, featuring a light gray sofa adorned with patterned cushions. Two side tables with lamps are positioned beside the seating. A textured area rug lies underfoot, and art prints are displayed on a wall shelf, enhancing the serene ambiance.
Home in Gretna
4.94 out of 5 average rating, 132 reviews

Cozy 3-bedroom home in Gretna on quiet street

Have fun and relax in this cute and comfortable home. Perfect for families, small groups, or couples this home will provide a serene place to recharge while away. Close to shopping, restaurants, coffee shops, hiking, and family-friendly activities: Vala’s Pumpkin Patch, Nebraska Crossing Outlet Mall, Strategic Air Command & Aerospace Museum, and Lee G. Simmons Wildlife Safari. Minutes to top-rated state parks and golf courses.

Guest favourite
Home in Omaha
5 out of 5 average rating, 6 reviews

West Omaha Townhouse

Relax in this bright, 3-bed, 2-bath Whitehawk gem! Enjoy an open floor plan, tasteful decor, and a sunny eat-in kitchen with stainless appliances that opens to a deck with green space views. The spacious primary suite features a walk-in closet, and the 2-car garage adds convenience. Located near a lake, trails, parks, and top dining and shopping—this is Omaha comfort at its best!

Popular amenities for Chicago holiday rentals

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