Vacation rentals in Orland Hills

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Top-rated vacation rentals in Orland Hills

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Guest favorite

Home in Lockport

4.95 out of 5 average rating, 117 reviews

Historic Hideaway ~ Vintage 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 favorite

Cottage in Merrillville

4.86 out of 5 average rating, 216 reviews

The Hideaway

This cozy cottage (lodging & renters only) located 30 minutes from Chicago is located on a private 3 acre property. It’s a private detached cottage from main house that sleeps four. One king size bedroom (2 air mattresses) (sheets supplied), large full bathroom with deep tub w/ handle (towels supplied), full kitchen (dishes, pots and pans ect supplied) private covered parking and yard (directly in front of cottage) w/ its own fire pit for enjoyment. No plug for electric cars (station 2 m away)

Guest favorite

Condo in Palos Hills

4.84 out of 5 average rating, 176 reviews

~Home Comforts, Roku SmartTV, Fast WiFi~

Enjoy the comforts of home in this first floor, private 2-bedroom condo in the SW Chicago Suburbs. We offer all the amenities you need. There are two queen beds, plus a full-size futon, full-size sofabed, and a very comfy couch your sleeping comfort. Enjoy the luxury of hotel quality sheets and plush towels, plus lots of pillows and blankets. We are near Moraine Valley Community College, Stagg High School, Palos Community Hospital, many forest preserves & trails, golf courses, and much more...

Guest favorite

Rental unit in Chebanse

4.96 out of 5 average rating, 543 reviews

Cathy's Little Farm Loft

Cathy's Little Farm loft is a new 500 sq ft apartment inside a storage barn on a wooded country acre. Fully appointed two story space offers peace and quiet. It is located close to I57, Walmart, Community College, Airport, Fair Grounds, National Guard Training Center, 15 minutes from Olivet, 60 miles south of Chicago. King size bed and twin size sofa sleeper upstairs, full size sleeper sofa in living room. Well equipped full size kitchen and laundry. Large lawn and garden area to enjoy.

Guest favorite

Home in Chicago

4.88 out of 5 average rating, 116 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 favorite

Guest suite in Naperville

4.95 out of 5 average rating, 371 reviews

Lake facing cozy little studio with private entry

This is a luxurious cozy little studio facing the lake, featuring a private entrance that is attached to a single family home. The studio is equipped with a top quality queen bed, an in-suite kitchenette including a mini fridge, microwave, and induction top, as well as a luxurious full bathroom. The studio is situated in the safest and friendliest neighborhoods in Naperville conveniently located close to cafes, restaurants, markets, a biking trail, and just minutes away from I88.

Guest favorite

Home in De Motte

4.95 out of 5 average rating, 231 reviews

Country Cottage

Looking for week-end get away? Traveling through Northwest Indiana on I-65 and looking for a quiet place to stay for the night? Situated on 6 acres and with convenient (2 mile) access to I-65, our cozy Country Cottage is a great choice! Enjoy the cottage feel of this recently renovated (new cabinets, flooring, appliances) and charmingly decorated home, located in close proximity to local attractions! Our 650 square foot cottage is ideal for 1 - 4 guests.

Guest favorite

Rental unit in Hammond

4.82 out of 5 average rating, 130 reviews

Plant MOOD FREE Wi-fi, parking, washer & dryer!

LATE CHECK-IN guest are welcome!!!! PLEASE READ MY FULL AIRBNB LISTING PRIOR TO BOOKINGS!!!! 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!

Superhost

Rental unit in Whiting

4.84 out of 5 average rating, 141 reviews

NEW! |Studio Apartment Whiting IN, United States#2

Welcome to the Charming town of Whiting! The charming town of Whiting is located on the southern shore of Lake Michigan. Whiting is neighbor to Hammond IN & Chicago IL. This space is only 2 minutes away from the skyway with easy access to the city of Chicago & only two blocks down from the Hammond Horseshoe Casino. These newly renovated units also offer a comfortable and convenient stay for those who would like to travel and explore both cities.

Guest favorite

Tiny home in Burr Ridge

4.92 out of 5 average rating, 339 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

Guest favorite

Rental unit in Blue Island

4.93 out of 5 average rating, 285 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 favorite

Rental unit in Palos Hills

4.94 out of 5 average rating, 164 reviews

Aunt Linda's Apartment with a View in Palos

Sunny, quiet, modest first floor 2 bedroom apartment in owner occupied 4-Flat apartment building. It is located in the Southwest corner of Chicago’s Cook County. It will easily accommodate 4 adults and 2 children [Note: long term stays are available.] The building's eastern view overlooks the southern suburbs of Chicago Ridge, Oak Lawn and Bridgeview.