Holiday rentals in Chicago Heights

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Top-rated holiday rentals in Chicago Heights

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

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Top guest favourite
A private outdoor gazebo houses a spacious jacuzzi, accompanied by soft lighting and a view of the surrounding greenery. Nearby, a wooden deck features a dining area with a table and chairs, inviting relaxation in a peaceful setting.
Guest house in Merrillville
4.94 out of 5 average rating, 158 reviews

Romantic Spa Getaway -Private Jacuzzi, Sauna, Pool

Romantic Getaway | Private Suite w/ Jacuzzi, Sauna, Pool & Gym Indulge in a luxurious, private retreat designed for couples! This beautifully styled guesthouse suite is attached to the main house but completely private—you’ll have your own private entrance for total seclusion. Enjoy spa-like relaxation with a jacuzzi, sauna, pool access, and a fully equipped gym. Perfect for honeymoons, anniversaries, or weekend escapes, our space blends comfort, privacy, and elegance for an unforgettable stay.

Top guest favourite
Flat in Hegewisch
4.91 out of 5 average rating, 239 reviews

Handicap accessible apartment w/Level-2 EV Charger

Just 12.5 miles from downtown in the extremely quiet Chicago neighborhood of Hegewisch. Walking distance to the South Shore train line, which can easily get you to Chicago museums and entertainment, or attractions in NW Indiana. Private parking in back also gives you the option of driving anywhere and then walking directly to your door, and outside cameras are present for security. Banks, restaurants, grocery, convenience, and liquor stores are all 1 block of the apartment for all your needs.

Guest favourite
A well-appointed bedroom features a spacious bed adorned with a soft blush and white blanket. A bedside lamp and decorative elements are present. Natural light filters through a window dressed with sheer curtains, creating a cozy ambiance. A small chair complements the interior design.
Flat in Hammond
4.85 out of 5 average rating, 170 reviews

1Plant MOOD FREE Wi-Fi Parking Washer/Dryer

PLEASE READ THE ENTIRE LISTING BEFORE BOOKING! LATE CHECKINS WELCOME! Enjoy FREE Washer/Dryer Full Kitchen + MORE! This special place is close to everything, making it easy to plan your visit. • I80, 294, 94 highways/tolls, etc. • Chicago • Shopping galore • A fun array of restaurants AND A LOT OF FREE PARKING! I’m extremely close to MUNSTER, HIGHLAND, SCHERERVILLE, DYER and many more Indiana locations! I’m extremely close to LYNWOOD, LANSING, CALUMET CITY, and many more Illinois locations!

Guest favourite
The modern kitchen features white cabinetry with marble countertops and stainless steel appliances. A window allows natural light to brighten the space, which includes a sink and a gas stove. Kitchen utensils and a dish rack are neatly organized within arm's reach.
Flat in Steger
4.95 out of 5 average rating, 19 reviews

Private Deluxe Apartment Clean, Safe & Affordable

Furnished modern apartment. Our new addition in our 4 unit complex for traveling professionals or visiting. New appliances, fully stocked kitchen, fresh linens & towels. Laundry room. Safe suburban location. 30 mi. to Chicago. Private off street parking up to 2 vehicles (even a bike parking) Clean, bright and organized. Strong Wifi (Xfinity Blast). Comfortable queen size bed, reclining sofa. 2 big screen TV's. Professionally cleaned spotless prior to arrival. Dozens of 5-Star reviews.

Guest favourite
A vibrant garden area is filled with a variety of lush green plants and colorful flowers. Stone elements lead to a small water feature, surrounded by dense foliage. The peaceful setting offers a natural retreat, inviting exploration or relaxation.
Flat in Homewood
4.92 out of 5 average rating, 104 reviews

Charming Garden Apartment

Make yourself at home in a charming apartment with all the amenities! Lose yourself birding or reading a book surrounded by lush gardens. Take a short walk to downtown Homewood to enjoy shopping & dining or catch the train to Chicago. 🏳️‍🌈 BLM Safe space! After a day of exploring, a king-sized sleep number bed & lush bathroom features will pamper you! A fold-down sofa creates an additional bed. Dogs welcome! This suite has a kitchenette with a convection toaster oven & induction cooktop.

Guest favourite
A spacious living area features a comfortable sofa and a grand piano, complemented by a decorative area rug on polished wooden floors. A window allows natural light to illuminate the room, and a small bookshelf adds a touch of warmth. A small dog with a scarf rests nearby.
Home in Homewood
4.93 out of 5 average rating, 105 reviews

Boulderstrewn: Historic Homewood home

Charming and historic Sears Catalog House on 2/3 acre wooded lot. Less than 10 minute walk to shops and restaurants in downtown Homewood to Metra rail (and Amtrak) station with express service to Hyde Park and University of Chicago (less than a half hour) and Chicago's 3 magnificent downtown waterfront stations (~40 minutes). Fire pit in yard can be used to enjoy summer nights. No cable, but several digital antenna channels available as well as Netflix, XBox and DVDs.

Superhost
A cozy living area is displayed with a pair of beige sofas, accented by decorative pillows. Framed wall art complements the decor. A soft rug is positioned on the wooden floor, while a lampshade on a side table adds subtle illumination.
Home in Blue Island
4.82 out of 5 average rating, 219 reviews

Warm and comfortable inviting Suburban home !

160 year old land mark community, Framed cedar bevel siding 2 story home, front porch , 10 ft high ceilings, kitchen canned lighting home. 6 feet fence In closed yard, whole house water filtration system , Quite neighborhood with sidewalks . 19 miles to downtown Chicago , Metra train station and bus route, in walking distance . driving to the city of Chicago 5 minutes to major expressways . Host is willing to be available for any and all information 24/7.

Top guest favourite
A charming single-story home is surrounded by lush greenery and colorful landscaping. The house features a light exterior with dark shutters and a welcoming front porch. A small tree adds a splash of color to the neatly manicured lawn.
Home in Munster
4.95 out of 5 average rating, 129 reviews

Cozy three bedroom home in Munster , Indiana.

Plan your next escape to Indiana or Illinois and stay in this beautifully renovated and thoughtfully appointed 3 bedroom and 1 bath home. Located in the quiet and safe suburb of Munster, Indiana, the property is just a 3 minute, easy access to the I-94 Highway. Exciting Downtown Chicago is just 30 minutes away! Walk to Riverside Park and take in the scenic view while enjoying a morning croissant and coffee from one of the quaint neighbourhood cafés.

Top guest favourite
The exterior of a private guest house is shown, featuring a detached two-story structure. A driveway leads to a garage with a white door, while a wooden staircase ascends to the entryway. The surrounding area includes greenery and paved walkways.
Guest suite in Crown Point
4.94 out of 5 average rating, 263 reviews

IT'S THE WRIGHT PLACE

Private guest house newly remodeled. One bedroom queen bed, bath w/shower, full kitchen stocked, including microwave and Keurig coffee maker pods included, family room TV, and WIFI. No matter if you are in town for work, sport competition, family or just vacationing we offer all the comforts of home. Air Mattress available upon request. Please treat as your own home, follow all house rules. No party or gatherings. This is a no smoking home.

Guest favourite
Home in Chicago Heights
5 out of 5 average rating, 10 reviews

The Heights of Chicago

Bring the whole family to this great place with lots of room for fun. Redesigned home with space for everyone! This property is located near walking trails, parks, close to shopping, food, and all the enjoyment’s that surround Chicago! Centrally located right outside of Chicago, close to the newest casino in the Chicagoland area! It’s the perfect place to bring friends and family

Guest favourite
The living area features a navy blue sofa and two matching armchairs positioned around a wooden coffee table. Natural light enters through large windows, adorned with sheer blue curtains. A cozy rug lies beneath the seating, enhancing a comfortable and inviting space.
Flat in Chicago
4.84 out of 5 average rating, 132 reviews

2 bedroom lovely spacious Suite

This stylish place to stay is perfect for any event. 420 friendly. Come and let us pamper you. Come and enjoy are tree lined community in the historical Beverly community. This Suite has all the latest amenities and beautifully furnished. Make some memories at this unique and family-friendly place.

Top guest favourite
A sunlit room features exposed brick walls and a sloped ceiling with a skylight. A spacious bed is centered against the wall, with light-colored bedding. A cozy armchair with a maroon cushion is placed nearby, alongside a light-colored area rug decorated with floral patterns.
Guest house in Edgewater
4.96 out of 5 average rating, 472 reviews

Cozy Coach House

Stairs lead up to a spacious, sunny, private living space, separate and peaceful- an oasis in the city on a quiet side street. Many public transit options to downtown Chicago or Evanston. Walk to Andersonville restaurant and shopping district.

Popular amenities for Chicago Heights holiday rentals

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