Holiday rentals in Orland Hills

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Top-rated holiday rentals in Orland Hills

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

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Guest favourite
A modern kitchen features sleek white cabinetry and stainless steel appliances. A central island serves as a dining space, complemented by two navy blue stools with gold accents. Pendant lights provide illumination, enhancing the contemporary feel of the room.
Home in Chicago
4.88 out of 5 average rating, 171 reviews

Boho Chic Coach House 30Min to downtown W/ Parking

Whether your looking to stay near family or be close to Downtown. This place has it ALL! This coach house is located in Mt greenwood which is one of the safest neighborhoods in the City of Chicago. It is home to many police, firefighters and teachers. Downtown is a quick 30 minute drive and there are also many bars and restaurants in walking distance. The home has been totally renovated and stocked with all the essentials. All you need to do now is pack your bags and enjoy your vacation.

Top guest favourite
A living area showcases a wooden entertainment center with a TV, flanked by a decorative console table and two lamps. The space features hardwood floors and a neutral color palette, complemented by a circular wall mirror. A staircase in the background leads to the upper level.
Apartment in Clarendon Hills
5 out of 5 average rating, 115 reviews

Apartment in Clarendon Hills.

Newly renovated Suite in multi family home in Clarendon Hills. Main level: fully equipped kitchen/island, dining area, living room & family room with fireplace. Upper level: Bedroom 1 - king size bed, walk in closet​, private bathroom/shower.​ Bedroom 2 - queen bed​, closet.​ Bedroom 3 - size bed​, closet. Living room has a pull-out sofa bed​. Family room with gas fireplace, access to deck/outdoor area.​ Easy access to restaurants, shopping (Oak Brook Mall minutes away), Metra, O’Hare.

Guest favourite
A cozy bedroom features a comfortable bed with a quilted cover and decorative pillows. A colorful textile art piece depicting Route 66 is displayed on the wall. A side table with a lamp adds to the charm, complemented by a vintage photograph hanging above.
Home in Lockport
4.96 out of 5 average rating, 164 reviews

Lockports Famous Hideaway ~ 2bdrm Guest House Flat

A history buff’s dream filled with antiques & artifacts relating to Chicago, Joliet, Lockport, the I & M Canal & "Route 66"! *Note: Pricing is based on "Double Occupancy". Extra charges per person apply after 2 guests. Can accommodate up to 6 guests. Family & Business Friendly. The entire upstairs 1,500 sq ft vintage 2-bedroom house apartment is all your own space. The flat is NOT shared with other guests/host. Private-entrance/self-check-in. Have a 'historic' stay at the "Hideaway"!

Guest favourite
A spacious living area is furnished with a large gray sectional sofa, accented by a black ottoman in the center. Natural light filters through the vertical blinds of two windows, while a round mirror adds a decorative touch to the wall.
Home in Tinley Park
4.9 out of 5 average rating, 21 reviews

Luxury Townhome in Tinley Park Near Shops & Train

Welcome to your luxury retreat in Tinley Park! This 3-level townhome features 3 spacious bedrooms, including a primary suite with en-suite, 2.5 bathrooms, a fully stocked kitchen, a large dining area, and an in-unit washer/dryer. Perfectly located near shops, restaurants, the Credit Union 1 Amphitheater, and just a short Metra train ride to downtown Chicago. Ideal for relaxation, business, or adventure—this space offers the perfect blend of comfort and convenience. Book your stay today!

Guest favourite
A spacious living area features a corner sectional sofa with soft cushioning and a cozy throw. Large windows provide natural light and city views. A simple coffee table sits in front, with light-colored carpet underfoot, enhancing the comfortable atmosphere.
Flat in Aurora
4.98 out of 5 average rating, 232 reviews

Penthouse In The Historic Hobbs

Experience luxury and historic charm at the Penthouse in the Historic Hobbs. Built in 1892, and restored in 2023, this new one bedroom corner unit offers a panoramic view of the Aurora skyline. Cook a delicious meal in the fully stocked kitchen. Dine at the bespoke table in the window bay under the iconic onion dome. Relax on the cozy sofa and enjoy a movie on the big screen TV. Rest in the plush king-sized bed. This urban retreat is near coffee, shopping, art and entertainment.

Top guest favourite
A sitting room features a beige sofa and a cream-colored armchair, positioned near a wooden desk. Two lamps provide soft lighting, while several framed photographs and artwork adorn the walls. Large windows allow natural light to fill the space, complemented by neutral-colored carpeting.
Guest suite in Orland Park
4.97 out of 5 average rating, 115 reviews

Private Guest Suite 2 Cozy Rooms

Private guest suite with separate entrance. Sitting room, kitchenette, bedroom w/queen bed, private bath, plus twin sofa bed in sitting room. Great alternative to hotel for business trip or visiting the area. Conveniently located in southwest suburbs of Chicago, 40 minutes from downtown by car (non rush hour) or Metra lines a few miles from the house. Set near a golf course and forest preserve, nearby to multiple restaurant and shopping districts less than 10 minutes away.

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
4.81 out of 5 average rating, 220 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.

Guest favourite
Flat in Lockport
4.96 out of 5 average rating, 99 reviews

Lockport Farmhouse: Private Entry+Parking By Door

Welcome to our charming Airbnb retreat in Lockport, Illinois! Enjoy the convenience of a full kitchen equipped with sleek stainless steel appliances. Kick back and relax in the cozy living room with a 55-inch smart TV featuring Roku for your entertainment needs. Convenience meets comfort with access to our on-site laundry room. Experience the perfect blend of modern amenities and rustic charm during your stay in Lockport. Book now for a delightful getaway!

Guest favourite
A corner jacuzzi whirlpool tub is positioned against a wall, featuring multiple jets for relaxation. A white toilet and a small wooden stool are visible nearby. Light gray walls are complemented by a window covered with a light-colored curtain, allowing natural light to filter in.
Home in Chicago Ridge
4.9 out of 5 average rating, 187 reviews

Quiet cul-de-sac with huge fenced in backyard

3 bedroom, 2 bath ranch home on a quiet cul-de-sac. Big fenced in backyard for the kids, dog, & adults to play during the day, then relax by the fire at night. Walking distance (50 ft.) to the bar/restaurant with private entrance. 15 miles (25 mins) from downtown Chicago. And for you couples, come back home from your busy day, sit back and relax in the 8 jet jacuzzi whirlpool tub that will comfortably fit both of you.

Guest favourite
A cozy living area is shown, featuring a blue leather couch with decorative pillows. An artistic fish sculpture adorns the wall beside colorful, patterned wallpaper. A small dining table with stools is visible, along with a refrigerator and natural light streaming through the window.
Home in Lockport
4.88 out of 5 average rating, 117 reviews

Island Time - Murals and more

Our charming and crooked, tropical-themed house🌴 is located one block from lively historic downtown Lockport. We are two blocks from train tracks, I & M Canal, and The Public Landing Restaurant. Near to Dellwood Park, Illinois State Museum, Lewis University, Joliet Junior College, Silver Cross Hospital, Chicagoland Speedway, and 30 miles southwest of Chicago. Minutes away from I-80, I-55, and I-355.🌿

Top guest favourite
A bright living room is showcased with a tan leather sofa and light-colored armchairs arranged around a coffee table. A TV is positioned on a wooden console. Natural light enters through sliding glass doors, leading to a small outdoor patio area.
Home in Manteno
4.99 out of 5 average rating, 102 reviews

Newly renovated modern home.

You will be comfortable in this newly remodeled two bedroom, two bathroom home. âś¶ 6.7Miles to Olivet Nazarene University âś¶ 8.4Miles to Riverside Medical âś¶ 11Miles to Kankakee River State Park âś¶ 43Miles to Midway Airport The home FEATURES: *Safe, quiet, walkable neighborhood *2 Bedroom; 2 King, 1 full Murphy bed *Spacious fully equipped kitchen with coffee station *Washing Machine, Dryer & Dishwasher

Top guest favourite
A ranch-style home is showcased with a welcoming facade of brick and siding. Large windows provide ample natural light, while a well-maintained garden features a variety of colorful flowers. A manicured lawn and sidewalk lead to the entryway, enhancing the inviting exterior.
Home in Worth
4.94 out of 5 average rating, 106 reviews

Worth It! 3 bedroom ranch home

Relax with the whole family at this peaceful place to stay. Just minutes from walking parks, outdoor concert venue, golfing, and down town! Comfy and inviting Ranch style home offers 3 bedrooms, a fully equipped kitchen, flat screen TVs, and large windows. The private backyard has a patio, and bbq grill. A real home away from home, we look forward to your new booking.

Popular amenities for Orland Hills holiday rentals

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Orland Hills