Holiday houses in Chicago

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Top-rated holiday rentals in Chicago

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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
4.88 out of 5 average rating, 96 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.

LocationFamilyWi-Fi

Guest favourite
A spacious outdoor deck overlooks the serene lake, featuring comfortable seating arrangements. A fire pit is positioned at the center, surrounded by metal chairs and a large umbrella for shade. The wooden deck is bathed in natural light, with trees framing the view.
Home in Waterloo
4.85 out of 5 average rating, 20 reviews

Surfer-Themed Lakefront Home

Peaceful Lakefront Getaway on Riverside Lake Escape to tranquility at this beautiful lakefront duplex on the serene 80-acre Riverside Lake. Wake up to peaceful water views, relax on the sandy beach just steps from your door, and enjoy the perfect balance of relaxation and adventure. Whether you’re sipping coffee on the patio, paddling on the lake, or roasting marshmallows by the fire pit, this home offers a peaceful retreat for couples, families, or solo travelers. Enjoy beach, firepit & fun!

FamilyLocationBeach

Top Guest favourite
A modern, single-story home features a welcoming front porch with two chairs positioned on a neatly landscaped lawn. The exterior combines sleek white siding and stone accents, complemented by a spacious driveway and a dark-colored garage door.
Home in Omaha
4.98 out of 5 average rating, 111 reviews

King Bed- Pool Table- Arcade Games - West Omaha

This luxurious West Omaha Home has everything you need for the perfect family Vacation. Featuring smart TVs in every room (both living room TV's are 85" & 75" with sound bars), board games, pool table with ping pong table topper, 14' trampoline, corn hole, large kids play-set W/ swings, BBQ and outdoor seating, double water heater, whole home filtration & a reverse osmosis system. The kitchen is fully stocked and we provide extra cooking appliances in the pantry. Minutes to parks & rec areas.

LocationValueGetting around

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
4.93 out of 5 average rating, 175 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.

ValueFamilyNearby

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, 116 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!

FamilyValueSleep quality

Superhost
Home in Chicago
5.0 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.

AccessHospitalityIndoor spaces

Top Guest favourite
Home in Omaha
5.0 out of 5 average rating, 42 reviews

Happily Home 4BR West Omaha/Elkhorn Retreat

Welcome to our West Omaha/ Elkhorn 4 bed 2 bath retreat nestled in a safe neighborhood just 5 minutes to premier shopping, tournament sites, and easy access to Downtown, Zoo, Vala's. Comfy, 5-Star Clean, and freshly remodeled, this home has all amenities, spacious gathering areas, and separate spaces when its time to recharge. -Fenced Yard, deck, grill, fire pit, garage parking, -Pet and Family Friendly. Woof woof -Walk to park w/pickleball, play structures

FamilyLocationPets

Guest favourite
An outdoor pool area features a large swimming pool with a waterslide. Surrounding the pool are multiple lounge chairs arranged for relaxation. An outdoor bar with high seating and a TV is visible under a covered patio, complemented by landscaped greenery in the background.
Home in West Omaha
4.92 out of 5 average rating, 190 reviews

👙☀️🏊‍♀️HEATED POOL | PRIVATE ESTATE | OUTDOOR BAR🌹🌺🌳

Great for events and big groups- My place ~ 6k sq ft, close to Dodge, 680/80. It is a quick drive to zoo, malls, airport, parks, Costco, grocery, restaurants, bars, regency, and more . You’ll love the outdoor space, seasonal pool (open after frost in March until mid October) & outdoor bar for entertainment, the ambiance, the neighborhood, and the comfy beds. My place is good for couples, business travelers, families (with kids), and small to big groups.

LocationFamilyHospitality

Guest favourite
Home in Omaha
4.98 out of 5 average rating, 94 reviews

Executive Rental 5BR+5BA | Arcade, GYM, Grill

Discover this completely renovated, fully furnished executive rental in West Omaha. This stunning 2-story home features gorgeous curb appeal and a light, airy feel. With 5 beds, 5 baths, a 3-car garage, and over 4300 sqft, it offers ample space for the whole family. Every bedroom has access to its bathroom. The home is fully furnished with all modern new furniture. The open foyer with soaring ceilings and a grand staircase leave a lasting impression.

LocationValueGetting around

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, 137 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!!

FamilyValueLaundry

Guest favourite
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.

LocationFamilyBarbecue

Guest favourite
A spacious modern home is displayed at dusk, with a well-defined driveway leading to a symmetrical facade that features two garage doors. The entrance is illuminated, highlighting the welcoming atmosphere. Dry grass surrounds the structure, offering a contrast to the warm hues of the setting sky.
Home in Omaha
4.93 out of 5 average rating, 41 reviews

Spacious Retreat in West Omaha 2 King 3 Queen Beds

Experience the best of Omaha from this spacious West Omaha retreat! This beautifully designed home features 5 bedrooms along with 3 FULL bathrooms and driveway parking. Located in a prime area, you're close to top dining, shopping, and entertainment, with easy access to all of Omaha. Perfect for families, business travelers, or groups looking to explore the city in comfort. Enjoy a stylish and fully equipped stay for a memorable visit!

LocationFamilyBathroom

Popular amenities for Chicago holiday rentals