Holiday rentals in Chicago

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Top-rated holiday rentals in Chicago

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

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Top guest favourite
Camper van/Motorhome in Omaha
5 out of 5 average rating, 15 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.

Top guest favourite
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, 206 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.

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
4.87 out of 5 average rating, 92 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 favourite
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 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
4.81 out of 5 average rating, 16 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!

Guest favourite
Home in Valley
5 out of 5 average rating, 11 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.

Guest favourite
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 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, 110 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!

Guest favourite
A comfortable living room space features a sectional sofa with decorative pillows. A large window allows natural light to fill the room, while a round coffee table sits in front. A dining area with sleek chairs is visible in the background, alongside a stylish wall clock.
Home in West Omaha
4.94 out of 5 average rating, 53 reviews

Stylish W. Omaha House. Shopping. King Suite.

This spacious 3 bedroom, 2.5 bath house rental is the ideal space for groups and families. Tucked away in a peaceful residential neighborhood, you can enjoy a tranquil and private stay while still having quick and easy access to the city's main road, W. Dodge (US Hwy 6). Plus, with the popular Village Pointe shopping mall just a short 5-minute drive away, you can indulge in some retail therapy or treat yourself to a delicious meal at one of the many restaurants in the area.

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, 32 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.

Top guest favourite
Home in Omaha
4.9 out of 5 average rating, 50 reviews

Your Home Away from Home

Experience comfort, convenience, and style in this beautifully maintained home perfect for families, couples, or business travelers. Located in a quiet, safe neighborhood, this fully furnished space offers everything you need for a relaxing stay — spacious bedrooms, a fully equipped kitchen, high-speed Wi-Fi, smart TVs, and cozy living areas.Freshly painted and new carpet installed.

Guest favourite
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
4.95 out of 5 average rating, 141 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.

Popular amenities for Chicago holiday rentals

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