Vacation rentals in Chicago

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Top-rated vacation rentals in Chicago

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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, 90 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.

Top 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, 90 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 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!

Guest favorite
The modern kitchen features wooden cabinetry paired with a white countertop. Four padded stools are arranged along the kitchen island. A stainless steel microwave and a light-filled door lead to the exterior. A mirror reflects the natural light from the window.
Home in Omaha
4.96 out of 5 average rating, 47 reviews

“The Duke” in Charming Old Towne Elkhorn

The Duke, is a roomy, stylish downtown Elkhorn retreat. Comfortably sleeps up to 8 with a king suite, a queen bedroom, & a third room with two full beds. 6 person Hot Tub Cook & bake to your heart’s content in a fully stocked kitchen (grill-ready tools included). Step outside onto the deck, enjoy fully fenced yard w/ morning coffee or evening drinks, & enjoy access to the shared hot tub for a relaxing soak after a day exploring Elkhorn. Perfect for families, groups, or weekend getaways.

Guest favorite
Cabin in Waterloo
4.95 out of 5 average rating, 42 reviews

Private Country Cabin for 2 on 25 acres

Reconnect with nature at this peaceful escape for up to 2 guest! The perfect place to disconnect and relax. You are partly "in the woods," but also walking distance from the main house. Our property is 25 acres with walking trails, a private 5 acre lake w/ paddle boats and kayaks for your use, and beautiful sitting areas throughout, including along the Platte River. If you want the great outdoors of camping without any of the roughing it, this is your place! Come Experience Rest!

Guest favorite
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, 170 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.

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, 108 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 favorite
Home in Omaha
5 out of 5 average rating, 34 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

Top guest favorite
Home in Omaha
4.99 out of 5 average rating, 85 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.

Guest favorite
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
4.92 out of 5 average rating, 37 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!

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
4.96 out of 5 average rating, 136 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.

Top guest favorite
The exterior of a two-story villa features a light blue facade with white accents. A large tree with pinkish leaves stands nearby, and a driveway leads to a garage. The front entrance is framed by a small set of steps and a welcoming porch.
Home in Omaha
4.93 out of 5 average rating, 124 reviews

2 bedroom villa with garage in quiet neighborhood

2 bedroom villa in a popular SW Omaha neighborhood. Near Village Point and lakeside shopping areas. Also close to many dining venues, movies, hospitals and more. 2 large bedrooms and a pull out couch in the lower level. Garage available for parking. Patio is open to the common area . Close to walking paths and park. Fully furnished with all necessities.

Popular amenities for Chicago vacation rentals

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