Vacation rentals in Chicago

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Top-rated vacation rentals in Chicago

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Guest favorite
A cozy outdoor seating area overlooks the river, featuring two woven chairs with light blue cushions. The spacious yard showcases lush greenery and a firepit area, with subtle views of the tranquil river in the background. Shade is provided by surrounding trees.
Cabin in Waterloo
4.87 out of 5 average rating, 89 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
Guest suite in West Omaha
4.88 out of 5 average rating, 170 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
A serene outdoor space is illuminated by soft lighting, highlighting a stone path leading to a well-designed guest house. Lush greenery surrounds a tranquil pond, with colorful flowers adding a vibrant touch. Comfortable seating areas are visible, inviting relaxation in a peaceful setting.
Guesthouse in Benson
4.93 out of 5 average rating, 135 reviews

Urban Oasis Studio

Escape to our Charming Guesthouse a perfect blend of comfort and relaxation. Step outside to enjoy a peaceful patio with a soothing waterfall. Stay comfortable A/C and heating, and cozy up next to the beautiful fireplace. High-speed Wi-Fi and a large TV are provided for your entertainment. On a fenced 3/4 acre lot, access to an outdoor firepit perfect for evening relaxation. Located in the heart of Omaha, you’ll enjoy full city access while still retreating to a peaceful, private setting.

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
4.91 out of 5 average rating, 119 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
Home in Council Bluffs
4.98 out of 5 average rating, 412 reviews

Cheerful two bedroom home in peaceful neighborhood

Relax with the whole family at this peaceful two bedroom home. Beautiful quiet neighborhood close to interstates, sports fields, IWCC, Henry Doorly Zoo, bike/running trails, downtown Omaha, Old Market, CHI Center, Eppley Airfield, and more. Spacious tree filled private backyard, outdoor patio, and grill. Plenty of parking. Great WiFi and Netflix, YouTube TV and Discovery+. Washer/dryer available. Dog friendly but no cats please. No gatherings, events, or parties inside or outdoors.

Top 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, 169 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.

Superhost
Guest suite in Omaha
4.79 out of 5 average rating, 240 reviews

Nestled in Nature

A mother-in-law suite perfect for individuals to families looking to stay in the prestigious Millard area. We are steps away from gorgeous Lake Zorinsky, golf courses, shopping, and other amenities. You can expect a friendly neighborhood, a full kitchen, gas fireplace, and natural light! Our shared backyard has a large fire pit, outdoor dining, and the gorgeous NE sunset. Lastly, check in is 6p and check out is 10a. *Please expect some noise from the main residence, above*

Top guest favorite
An outdoor seating area features several wooden chairs and tables surrounding a central fire pit. The space is paved with bricks, providing a clean, defined gathering spot. Green grass and a fenced yard create a spacious and open atmosphere for relaxation.
Home in Waterloo
4.91 out of 5 average rating, 107 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
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, 130 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!!

Top guest favorite
A spacious living area is highlighted by a beautifully decorated Christmas tree adorned with lights. Expansive windows frame a view of the outdoors, while dark wood flooring adds warmth to the scene. A foosball table is visible in the background, enhancing the recreational appeal.
Home in Omaha
4.96 out of 5 average rating, 104 reviews

Hangar 1 with a river view

Large secluded home with a private drive and an amazing view! This three bedroom, three full bath home with an aviation theme, has plenty of space with a view of the Missouri River and a hot tub off of the master. Three queen beds, a twin with a twin trundle, and a pull out couch can sleep up to 10. Foosball and air hockey tables. There is a bike path at the end of the driveway and only a 7 min drive to Eppley Airfield.

Top guest favorite
Home in Omaha
4.95 out of 5 average rating, 315 reviews

*Romantic* Rose Cottage with Hot Tub in Benson

Romantic Rose Cottage, north Benson. Minutes from UNMC, Downtown, CWS, CHI Center, Zoo, Dundee & Benson Restaurants. Beautifully designed space, perfect for short getaways and comfortable for long term stays . Wood floors, Essential cooking items, Breakfast nook with table for dining/work space. Large off street parking for 2 cars. Washer & Dryer in basement. Furry family members welcome. Fully fenced back yard.

Popular amenities for Chicago vacation rentals

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