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
Guest suite in Omaha
4.87 out of 5 average rating, 117 reviews

Private Lakefront Retreat| Pool•Hot tub •Sauna•SPA

Private Lakefront Walk-out basement is perfect for families & business travelers Your own resort in the city. No parties allowed! Newly remodeled space with Pool, Hot tub & Sauna Spacious living room with foosball & pool table, sleeper sofas Full kitchen Cozy bedroom with king-size bed & TV 2 bathrooms Breathtaking backyard, various patio options, BBQ, dock for meditation & fishing Close to Dodge & Interstate, Topgolf, grocery stores & Costco, restaurants 15min to the Zoo, Airport & Downtow🏡

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.

Superhost
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, 162 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 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.

Superhost
Guest suite in Omaha
4.79 out of 5 average rating, 235 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!

Top guest favourite
A bright living area presents large windows allowing natural light to fill the space. Comfortable teal sofas and a wooden coffee table create a casual atmosphere. A dark wood TV stand supports a flat-screen television, while a soft rug lies underneath, adding texture to the floor.
Guest house in Blackstone
5 out of 5 average rating, 232 reviews

The Hidden Garden at Blackstone

Newly renovated second floor of a carriage house located on a historic property in the popular Blackstone District. Shares an acre of land with the main house, built in 1892 and occupied by the owners. Although situated in the middle of the city, the unit feels secluded from its urban environment and looks out onto a garden surrounded by trees, shrubs and flowers and is in walking distance to many restaurants and bars in both the Blackstone District and Midtown Crossing.

Top guest favourite
A cozy seating area features floral-patterned cushions on a built-in bench, complemented by an ornate coffee table. Natural light enters through a nearby window, and decorative wall hangings provide charm to the space. A polished wooden cabinet enhances the warm atmosphere.
Guest suite in Omaha
4.98 out of 5 average rating, 197 reviews

2000 sq ft-2 car garage-dog friendly-private entry

2000 sq ft. Private Floor. Bedroom has California king, second king bed with privacy curtains, queen pull out. All beds have TVs. Washer/dryer, Kitchenette, 2 car garage. WIFI, Cable. Gym with Treadmill, Bike, Weights, Foosball, Key board, record player, TV, etc. Enjoy greenhouse and outdoor eating area. Walkable neighborhood facing Happy Hollow Club, 2 minutes from I80. Continental breakfast included. Dogs enjoy run of fully fenced yard .

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, 124 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
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, 133 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.

Top guest favourite
Flat in Ralston
4.98 out of 5 average rating, 330 reviews

Highland Hideaway

Cozy apartment with fireplace; Enjoy a morning cup of coffee or an evening glass of wine on the patio. Located in the lower level of my home--Private entrance with key code entry and off-street parking. Easy access to I-80. The perfect setting for a romantic getaway, family visit, fun-filled girls' weekend, or business trip. Whoever you are and whatever your needs may be, I invite you to come enjoy my Highland Hideaway!

Top guest favourite
Townhouse in Omaha
4.92 out of 5 average rating, 107 reviews

Modern & Charming Home near Village Pointe

- Revel in a spacious home, perfect for families or groups seeking privacy. - Newly equipped kitchen with modern appliances and breakfast counter. - Prime location near shopping, dining, and major road access for convenience. - Quiet, residential area with easy access to Omaha's popular attractions. - Experience comfort and space today; book your stay with us now!

Popular amenities for Chicago holiday rentals

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