Holiday rentals in Orland Park

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Top-rated holiday rentals in Orland Park

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

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Top 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, 153 reviews

Lockports Famous Hideaway ~ 2bdrm Guest House Flat

A history buff’s dream filled with antiques & artifacts relating to Lockport, Chicago, Joliet, I & M Canal & "Route 66"! If you have roots in Illinois or Lockport, the Hideaway is for you! 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. Family & Business Friendly. Private-entrance/self-check-in. *Can accommodate up to 6 guests. Extra charges apply after 2 guests. Have a 'historic' stay at the "Hideaway"

Guest favourite
A spacious artist loft features a living area with hardwood floors and large windows allowing natural light. A leather sofa is positioned in the center, with stylish chairs nearby. The open kitchen is visible in the background, along with a modern dining space under soft lighting.
Loft in Brookfield
4.91 out of 5 average rating, 134 reviews

1920s fully updated unique open artist loft space

True artist living loft space!!! One of a kind space in a safe area of the western suburbs close to the city and easy commute to shops stores. very close to trains buses and expressways. Private parking lot. No unit above or below. Quiet and private spacious updated wide open loft. Hardwood floors throughout forced heat and ac slated steel designer bathroom.. Double oven dishwasher electric cooktop sub zero fridge microwave and toaster oven. Ceiling fans two beds. Can sleep 6 for added cost

Guest favourite
A modern kitchen is presented, featuring stainless-steel appliances including a refrigerator and a gas range. Light wood cabinetry complements the white tiled backsplash, while a mat is placed in front of the sink area, enhancing the functional design.
Flat in Worth
4.88 out of 5 average rating, 24 reviews

Charming 1-Bedroom in Worth, IL

Welcome to your cozy retreat in Worth, IL! This newly remodeled one-bedroom apartment is perfect for a comfortable and convenient stay. Inside, you’ll find a spacious bedroom with a queen bed, fully equipped kitchen with brand-new stainless-steel appliances, an updated bathroom with modern fixtures, and two Smart TVs and highspeed Wi-Fi. Conveniently situated in the South Suburbs of Chicago near shops, parks, and dining, you’ll also have easy access to major highways and public transportation.

Superhost
A comfortable living area features a patterned sofa and armchair, positioned near a decorative fireplace. A small table is set with items, while a dining area is visible in the background. Natural light enters through the window, enhancing the cozy ambiance.
Flat in Lemont
4.86 out of 5 average rating, 81 reviews

Burr Oak

Nestled in the Palos Forest Preserve with access to many miles of hiking and biking trails . Spacious one bedroom basement apartment with private entrance. 6 minutes to The Forge, 7 minutes to Target, 8 minutes to downtown Lemont restaurants. 4 minutes to Little Red Schoolhouse, 7 minutes to Burr Ridge shopping and dining. 22 minutes to Midway 32 minutes to O'Hare. Half hour to the Loop. 20 minutes from Ikea and Bass Pro. Very quiet cabin like setting. Ask about our extended stay discounts.

Superhost
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
4.94 out of 5 average rating, 16 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 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
4.87 out of 5 average rating, 157 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.

Guest favourite
A spacious bedroom features a modern black metal bed with crisp white linens and decorative pillows. Soft, neutral colors enhance the space, complemented by a large mirror and a small desk. Natural light enters through a window covered with light curtains, creating a calm atmosphere.
Flat in Lockport
5 out of 5 average rating, 16 reviews

Bright Lockport Farmhouse: King Bed + Yard View

Discover your ideal getaway in our charming Lockport, Illinois, Airbnb! This inviting retreat features a full kitchen with stainless steel appliances, an island for prepping food, a coffee bar for your morning brews, and tons of sunlight! Unwind in the cozy living room, complete with a 65-inch Roku TV and board game wall. Enjoy the convenience of a shared on-site laundry room. Experience the perfect mix of modern comforts and rustic charm in Lockport. Secure your booking today!

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, 111 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.

Guest favourite
A walkway lined with pavers is framed by greenery, leading toward a fenced yard. Soft string lights illuminate the area beside the tiny house, creating a serene evening atmosphere. A cozy seating area is visible, inviting relaxation outdoors near the lush foliage.
Tiny home in Burr Ridge
4.9 out of 5 average rating, 405 reviews

Less is more! Pet friendly Tiny Home near Chicago!

Less is more--see for yourself how big 250 square feet can really feel! For those who would love to try tiny living and a minimalist lifestyle, this is the perfect getaway. This tiny house has everything you will need to fall in love with tiny living! There is a fenced yard, grass area for furry friends, free parking and is close to hiking trails, restaurants, shops, breweries, bars, and Chicago! Check us out on Insta: @LessIsMore_TinyHome

Top guest favourite
A cozy living area is featured with two large windows allowing natural light to fill the space. A hanging chair adds a unique touch, while a dark sofa and a coffee table sit on a patterned rug. A television is positioned on a stand nearby.
Flat in Blue Island
4.94 out of 5 average rating, 308 reviews

Charming Unique 2 Bdrm Apartment in Victorian Home

My place is close to the excitement and culture of the beautiful city of Chicago. It is a short walk to Metra trains with a 25 minute ride downtown. You’ll love my place because of the diverse, comfortable, quiet, tree lined neighborhood where you can relax and feel secure. It is close to expressways, golf courses and a local park with walking path. The apartment is not available to guests without previous positive reviews.

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
4.92 out of 5 average rating, 166 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
Guest suite in Oak Lawn
5 out of 5 average rating, 11 reviews

Oak Lawn remote workers retreat

Discover the perfect blend of comfort and convenience in this newly remodeled walkout basement studio, located in the prestigious Midlothian Country Club neighborhood. This charming rental offers a separate entrance and access to the main floor laundry, ensuring your privacy and ease of living. Perfect for Medical Professionals and Relocators: A great fit for those in the medical industry or those relocating.

Popular amenities for Orland Park holiday rentals

Quick stats about holiday rentals in Orland Park

  • Total holiday rentals

    Explore 10 holiday rentals in Orland Park

  • Nightly prices starting at

    Orland Park holiday rentals start at € 26 per night before taxes and fees

  • Verified guest reviews

    Over 260 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    10 of Orland Park holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Orland Park rentals

  • 4.8 Average rating

    Orland Park stays are highly rated by guests – averaging 4.8 out of 5!

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