Vacation rentals in Chicago

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Top-rated vacation rentals in Chicago

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

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Top guest favorite
Camper/RV in Omaha
5 out of 5 average rating, 17 reviews

Dottie the 1969 Vintage Camper for Glamping

Enjoy our kitschy 1969 camper tucked away in the woods of a private neighborhood in the city, it's a vintage glamping dream! Cozy and comfortable with a cushy bed (A few inches shy of a double. 6ft 3in x 4ft), it's a playhouse for grownups! The camper sits in its own corner of our property, surrounded by 1 acre of beautiful gardens. Tucked near a creek and trees with a fire pit and hammock, it's a perfect couple's get-a-way close to coffee shops, dining and shopping. Ceiling hight is 70" inside.

Top guest favorite
A sign reading 'Quirky Place' is prominently displayed against a light wood-paneled wall. Below the sign, a planter contains a variety of succulents, including a large cactus and smaller green plants, adding a touch of greenery to the entryway.
Place to stay in Omaha
4.94 out of 5 average rating, 209 reviews

Quirky Mid-Century Studio Near Omaha Favorites

Welcome to The Quirky Place a cozy, private Omaha studio with mid-century charm, modern touches, and personality. This comfortable space includes a Murphy bed with a super comfortable mattress, and a sofa bed, a 3/4 bath, fully stocked kitchen, driveway parking, space for up to 4 guests. Perfect for a quick getaway, work trip, concert, medical visit, family stay, or weekend get away. Cheerful, comfortable, a little unexpected, and easy to settle into...a bit more fun and a lot more interesting.

Guest favorite
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, 95 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 favorite
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, 172 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 favorite
Home in Benson
4.98 out of 5 average rating, 110 reviews

"Cozy Cottage" Getaway, Hot Tub & Fireplace Benson

Charming cottage nestled in Omaha's vibrant Benson neighborhood, near 60th & Manderson. 15 mins Downtown, Convention center, ball park, Zoo & Museums Perfect for a quiet getaway, romantic retreat or extended work stay with a mix of privacy & convenience. Fully equipped kitchen, modern bath, comfortable bed, easy to use gas fireplace (off during hot summer months) and Hot tub for 2 on private deck. Benson is known for it's live music, unique restaurants, craft breweries and local shops.

Top guest favorite
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 West Omaha
4.92 out of 5 average rating, 130 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.

Superhost
Home in Chicago Precinct
5 out of 5 average rating, 3 reviews

Exquisite Elkhorn Experience

Come experience Elkhorn at its finest! Brand-new 5-bed, 3-bath ranch in the desirable South Elkhorn/Gretna area! This spacious home features an open-concept living, dining, and kitchen area, a finished basement, and a fenced backyard. Modern finishes and plenty of room to spread out make it the perfect home base for families, business travelers, medical stays, sports teams, and extended visits. Conveniently located near shopping, dining, parks, and easy access to Omaha.

Superhost
Home in Omaha
5 out of 5 average rating, 4 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 favorite
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, 136 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 favorite
The front exterior of a light-colored house is shown, featuring a well-kept lawn and stone pathway leading to the entrance. Flower beds with green foliage are visible beside the steps. Large windows allow natural light to enter, while neighboring homes are subtly discerned in the background.
Home in Omaha
4.88 out of 5 average rating, 33 reviews

Cheerful 3 bd home with easy access to interstate!

A fun home great for a family or multiple adults! 3 bed, 2.5 bath home, that sleeps 8. Located in a quiet, friendly family neighborhood in West Omaha. Located close to top notch outdoor shopping and fantastic restaurants (Village Pointe). Around the corner from the MARK family fun center and UBT sports center! 25 min drive to downtown Omaha. Amenities: Free Wi-Fi, 2 TV's, Patio, Grill, Spacious Back Yard, 2 car garage, Full Kitchen, Laundry.

Top guest favorite
A vibrant living area features contemporary furniture, including a leather sofa and multicolored chairs around a glass dining table. A striking abstract painting adds color to the wall, while natural light streams in from two window panes framed by light curtains.
Tiny home in Omaha
4.93 out of 5 average rating, 246 reviews

Contemporary Furnished Home

A cozy place with contemporary furnishing. A home away from home of your own with gated concrete driveway. Tennis court area welcomes you each day for your daily exercise. Full kitchen and laundry are among the amenities provided for your additional comfort. Grocery stores and restaurants are just minutes away to satisfy your cravings early morning or late nights. Multiple gas stations & churches are are just around the corner.

Guest favorite
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
4.94 out of 5 average rating, 144 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.

Popular amenities for Chicago vacation rentals