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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Guest favourite
A spacious living area features two grey sofas, one with an attached chaise lounge, arranged around a rustic wooden coffee table. Soft lighting is provided by a ceiling fan above, while a textured area rug adds warmth to the tiled floor.
Cabin in Waterloo
4.87 out of 5 average rating, 90 reviews

Charming riverfront house

This quiet & serene riverfront house is the perfect setting for a family, nature lovers, fishermen, anniversaries, friends retreats, or honeymooners! Newly remodeled in 2018, we can sleep up to 12. Located just a couple of miles outside of Elkhorn & directly on the Elkhorn River, this is a nature-lovers haven! Local restaurants, shopping & other amenities in Elkhorn, Omaha & Waterloo are within a few minutes drive! Our place is a smoke & pet free home! Smoking is allowed in outdoor areas only.

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 West Omaha
4.88 out of 5 average rating, 171 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
Home in Omaha
4.95 out of 5 average rating, 55 reviews

Family Fun Basement Retreat w/ Hot Tub Near Dining

Spacious Basement Retreat – Private Entrance This rental is for the basement level only, with a private entrance and a locked door separating it from the upstairs. 2 private bedrooms, a daybed with trundle, 1 full bath, living room with TV, and bar area that seats 4. Fun extras: foosball table, shuffleboard, hot tub, outdoor TV, and board games. The backyard backs up to trees, offering a peaceful and quiet escape. Just minutes from local attractions, dining, shopping, and family fun!

Guest favourite
The modern kitchen features wooden cabinetry paired with a white countertop. Four padded stools are arranged along the kitchen island. A stainless steel microwave and a light-filled door lead to the exterior. A mirror reflects the natural light from the window.
Home in Omaha
4.96 out of 5 average rating, 47 reviews

“The Duke” in Charming Old Towne Elkhorn

The Duke, is a roomy, stylish downtown Elkhorn retreat. Comfortably sleeps up to 8 with a king suite, a queen bedroom, & a third room with two full beds. 6 person Hot Tub Cook & bake to your heart’s content in a fully stocked kitchen (grill-ready tools included). Step outside onto the deck, enjoy fully fenced yard w/ morning coffee or evening drinks, & enjoy access to the shared hot tub for a relaxing soak after a day exploring Elkhorn. Perfect for families, groups, or weekend getaways.

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, 171 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
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
4.91 out of 5 average rating, 109 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!

Superhost
Home in Omaha
5 out of 5 average rating, 3 reviews

Millard/Elkhorn Whole house, 4 bedrooms!

Relax with the whole family at this homey place to stay. With 4 bedrooms, 5 beds, two living spaces, two dining spaces, a full kitchen, kitchenette, and plenty of parking, the whole family can enjoy all the fun Omaha has to offer, whether you are here to visit our world famous zoo, enjoy the College World Series, or visit nearby family and friends. Overlooking a wooded area, the deck with grill allows access to a large open backyard and is a peaceful place to relax!

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, 131 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!!

Top guest favourite
Home in Omaha
4.9 out of 5 average rating, 50 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.

Guest favourite
A screened-in patio is visible, providing a serene outdoor space for relaxation. The area includes a small table and two chairs. A grassy lawn extends in front, with a flower blooming near the patio entrance and large windows in the background allowing light into the home.
Home in Omaha
4.95 out of 5 average rating, 193 reviews

Private basement apartment w/ separate entrance

My place is close to I-680. 15 minutes to downtown, 10 minutes to Benson and 17 minutes to airport..Close to Immanuel Hospital and Omaha Country Club. You’ll love my place because of Private entrance, nice quiet country feel on the edge of town. You enjoy the screened in patio, your own bath and kitchen.. My place is good for couples, solo adventurers, and business travelers.

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 Omaha
4.95 out of 5 average rating, 138 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, 125 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