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.

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
Home in Valley
4.94 out of 5 average rating, 17 reviews

Private Waterfront Lake House | Near Omaha

Modern lakefront retreat in Valley, minutes from Omaha, the Elkhorn Athletic Association, DC West, and wedding venues such as Countryside and A View West Shores, plus Village Pointe. Located on a peaceful no-wake lake, this home features open living, water views, a king suite, queen bedroom, full-over-full bunk room, and loft sleeping area. Ideal for weddings, tournaments, school events, and weekend getaways. Enjoy sunset views and a relaxing lakeside setting with direct backyard lake access.

Guest favorite
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!

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.

Top guest favorite
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, 113 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 Chicago Precinct
5 out of 5 average rating, 4 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.

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.

Top guest favorite
Apartment in Ralston
4.98 out of 5 average rating, 354 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!

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