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.

Top guest favourite
The spacious walk-out basement includes a queen bed and a bunk bed, with light beige linens complementing the warm décor. A seating area features a cozy sofa and a coffee table, while artwork and shelves add character to the room.
Guest suite in Omaha
4.92 out of 5 average rating, 60 reviews

Private Walkout Basement;FullWasher/dryer

Enjoy a private walk-out basement located in a West Omaha, family-friendly neighborhood! The house backs up to a beautiful walking path that runs parallel to the creek and a prairie reserve. We have two dogs, so if you bring a pet, please know the backyard is a shared space! Pets are certainly welcome! We are passionate about hosting guests and creating comfortable and cozy spaces. At our other Airbnb property, we get a lot of comments about the comfy beds, and we have the same kind here!

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
4.94 out of 5 average rating, 355 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, 232 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, 102 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
The exterior of the home is featured, showcasing a charming ranch-style design with a well-maintained lawn. A flagpole holds a waving American flag, while the driveway leads to a two-car garage. Lush greenery and landscaped stones frame the welcoming entrance.
Home in Omaha
5 out of 5 average rating, 12 reviews

Just like home!

Welcome to our cozy Millard home! This quiet, centrally located spot features a comfy kitchen for snacks or family meals. The master bedroom has a super comfy split king adjustable bed, while the guest room offers a two twin beds that can be moved together for a King. Relax in the living room with a reclining couch and loveseat, perfect for movie nights. Enjoy the deck with a warm fire pit or cook a meal outside. We hope you have a wonderful stay!

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, 181 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!!

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!

Top guest favourite
The living area features a blue couch with decorative pillows and a black reclining chair. A small footrest is placed in front of a patterned area rug. Natural light enters through a window with sheer curtains, while a standing fan enhances the comfort of the space.
Flat in Papillion
4.84 out of 5 average rating, 328 reviews

Bird Nest Hideaway, Cozy, Quiet, Downtown Papio

Cozy apartment located in the lower level of home; Private entrance with keyless code entry, and private driveway. Centrally located with easy access to I-80. The perfect setting for couples looking for a getaway, families visiting Omaha, people in town on business, or a fun-filled weekend. Whoever you are and whatever your need may be, I invite you to my Bird's Nest Hideaway!

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, 125 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, 119 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

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