Holiday rentals in Chicago

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chicago

Guests agree: these stays are highly rated for location, cleanliness and more.

%{current} / %{total}1 / 1
Superhost
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 Omaha
4.89 out of 5 average rating, 165 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 favourite
A tranquil outdoor space features a decorative pond surrounded by a stone border, with colorful pots containing flowers and plants. Two green chairs with patterned cushions are positioned nearby. The background displays a cozy guest house and vibrant greenery, providing a peaceful retreat.
Guest house in Benson
4.91 out of 5 average rating, 115 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.

Top guest favourite
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 Omaha
4.9 out of 5 average rating, 110 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 favourite
A rustic farmhouse is seen in the distance, surrounded by green fields and a neatly plowed crop area. A large barn and a silo are positioned on the property, with trees lining the background under a clear blue sky.
Farm stay in Glenwood
4.98 out of 5 average rating, 239 reviews

Ellington Place

A rustic farmhouse retreat on a crop producing farm, which means we could be planting or harvesting during your stay. Ellington Place has a furnished kitchen, updated bathroom and washer and dryer. Along with excellent outdoor entertainment, complete with a fire pit, porch for sitting and open area for short walks. The property is located 25 minutes from the Omaha metro area as well as less than 10 minutes from the Wabash Trace, a bike trail that travels through Mills County.

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
4.9 out of 5 average rating, 102 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 favourite
A bright living area presents large windows allowing natural light to fill the space. Comfortable teal sofas and a wooden coffee table create a casual atmosphere. A dark wood TV stand supports a flat-screen television, while a soft rug lies underneath, adding texture to the floor.
Guest house in Blackstone
5 out of 5 average rating, 243 reviews

The Hidden Garden at Blackstone

Newly renovated second floor of a carriage house located on a historic property in the popular Blackstone District. Shares an acre of land with the main house, built in 1892 and occupied by the owners. Although situated in the middle of the city, the unit feels secluded from its urban environment and looks out onto a garden surrounded by trees, shrubs and flowers and is in walking distance to many restaurants and bars in both the Blackstone District and Midtown Crossing.

Top guest favourite
A cozy seating area features floral-patterned cushions on a built-in bench, complemented by an ornate coffee table. Natural light enters through a nearby window, and decorative wall hangings provide charm to the space. A polished wooden cabinet enhances the warm atmosphere.
Guest suite in Omaha
4.98 out of 5 average rating, 198 reviews

2000 sq ft-2 car garage-dog friendly-private entry

2000 sq ft. Private Floor. Bedroom has California king, second king bed with privacy curtains, queen pull out. All beds have TVs. Washer/dryer, Kitchenette, 2 car garage. WIFI, Cable. Gym with Treadmill, Bike, Weights, Foosball, Key board, record player, TV, etc. Enjoy greenhouse and outdoor eating area. Walkable neighborhood facing Happy Hollow Club, 2 minutes from I80. Continental breakfast included. Dogs enjoy run of fully fenced yard .

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, 126 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 favourite
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 Keystone
4.94 out of 5 average rating, 232 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 favourite
A comfortable living area is shown, featuring a light gray sofa adorned with patterned cushions. Two side tables with lamps are positioned beside the seating. A textured area rug lies underfoot, and art prints are displayed on a wall shelf, enhancing the serene ambiance.
Home in Gretna
4.94 out of 5 average rating, 136 reviews

Cozy 3-bedroom home in Gretna on quiet street

Have fun and relax in this cute and comfortable home. Perfect for families, small groups, or couples this home will provide a serene place to recharge while away. Close to shopping, restaurants, coffee shops, hiking, and family-friendly activities: Vala’s Pumpkin Patch, Nebraska Crossing Outlet Mall, Strategic Air Command & Aerospace Museum, and Lee G. Simmons Wildlife Safari. Minutes to top-rated state parks and golf courses.

Top guest favourite
Flat in Ralston
4.98 out of 5 average rating, 332 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!

Top guest favourite
Townhouse in Omaha
4.92 out of 5 average rating, 107 reviews

Modern & Charming Home near Village Pointe

- Revel in a spacious home, perfect for families or groups seeking privacy. - Newly equipped kitchen with modern appliances and breakfast counter. - Prime location near shopping, dining, and major road access for convenience. - Quiet, residential area with easy access to Omaha's popular attractions. - Experience comfort and space today; book your stay with us now!

Popular amenities for Chicago holiday rentals

  1. Airbnb
  2. United States
  3. Nebraska
  4. Douglas County
  5. Chicago