Vacation rentals in Chicago

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Top-rated vacation rentals in Chicago

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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.

Top guest favorite
Camper/RV in Omaha
5.0 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 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?

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, 94 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 spacious living room is highlighted by a comfortable sectional sofa adorned with various pillows. A large painting of clouds and a peaceful landscape is mounted on the wall. Natural light filters in through sliding glass doors that lead to a deck.
Home in West Omaha
4.97 out of 5 average rating, 92 reviews

West Omaha Townhouse with GYM, Shopping, King Bed

5 min drive to Village Pointe! Welcome to your perfect group or family getaway! Newly built in 2022, located in a lovely residential neighborhood, this charming home invites you to experience the best of both worlds - relaxation and exploration. Just a quick drive or rideshare away, you'll find shopping, restaurants, and vibrant night life. Conveniently situated off West Dodge Rd (US Hwy 6), making it easily accessible from anywhere in town. This rental includes 3 beds/3 baths, and a home gym.

Guest favorite
Home in Valley
4.94 out of 5 average rating, 16 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.

Top guest favorite
Home in Benson
4.98 out of 5 average rating, 108 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.

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, 112 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
New place to stay

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.

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.

Popular amenities for Chicago vacation rentals