Vacation rentals in Orland Park

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Top-rated vacation rentals in Orland Park

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Guest favorite

Loft in West Dundee

4.97 out of 5 average rating, 442 reviews

Hip Urban Loft - Small Town Charm - 124 LOFTS #2

Luxury one-bedroom loft in the heart of downtown Dundee. Newly renovated 125-year-old building with timber ceilings, exposed brick walls and beautifully restored hardwood floors. Tastefully decorated and features a king-size Beautyrest mattress, luxury bed linen, private bathroom, kitchenette with under counter refrigerator, Kuerig coffee maker and lightning fast Wi-Fi for streaming your favorite shows on the 60” LED smart TV. 124 LOFTS offers 4 separate luxury lofts. Loft 2 is our most spacious

Feb 2 – 9

ﺩ.ﺇ512 per night

Guest favorite

Farm stay in De Motte

4.94 out of 5 average rating, 113 reviews

Cozy barn loft on organic vegetable farm

Find peace and restoration in this beautiful barn loft at Perkins' Good Earth Farm. The loft has a bedroom, separate shower and toilet spaces, work area, sitting room, kitchen space, and heating/cooling fresh air system. Located above our farm store, the loft provides privacy for you while giving you access to fresh fruits & veggies, locally sourced meats, homemade soups & salads from our farm kitchen, and so much more. You can also walk our farm trails, visit the veggies, or enjoy a campfire.

Dec 27 – Jan 3

ﺩ.ﺇ316 per night

Guest favorite

Condo in Palos Hills

4.84 out of 5 average rating, 166 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...

Nov 16 – 23

ﺩ.ﺇ551 per night

Guest favorite

Apartment in Homewood

5.0 out of 5 average rating, 39 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 lovely downtown Homewood to enjoy shopping & dining or catch the train to Chicago. After a day of exploring, a king-sized sleep number bed and lush bathroom features will pamper you! A fold-down sofa creates an additional bed. Dogs are welcome! This suite has a kitchenette with a convection toaster oven, induction cooktop, and fridge!

Aug 29 – Sep 5

ﺩ.ﺇ333 per night

Guest favorite

Cottage in Gary

4.96 out of 5 average rating, 114 reviews

Neon Dunes Vista Beachfront Cottage

Neon Dunes Cottage is perfect for a romantic getaway. A newly renovated cottage with new kitchen, modern appliances and new bathroom all in a bright airy home. It is located in Indiana Dunes National Park/Miller Beach. Only 1.5 blocks to the beach, you can hike trails nearby and come back to relax in a unique, comfortable setting with ambiance and charm. It's perfect for summer/holidays. Wifi, onsite parking and self check in, allow you to enjoy our wonderful home in privacy and peace.

Dec 8 – 15

ﺩ.ﺇ561 per night

Guest favorite

Guest suite in Orland Park

4.99 out of 5 average rating, 71 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.

May 25 – Jun 1

ﺩ.ﺇ445 per night

Guest favorite

Home in Joliet

4.83 out of 5 average rating, 157 reviews

Cozy Private Cottage in the Cathedral District

Our cozy, 1920's home is located in the Cathedral district in Joliet. 3 minutes away from the Haley Mansion and 6 minutes away from the Jacob Henry Mansion. You get the whole main floor for yourself and your guest(s) with your own entrance through the front door that has a keypad door lock. I along with my two mini dachshund puppies stay in the basement. We have our own entrance through the back. You can park right outside on the street. So there is plenty of parking.

Sep 22 – 29

ﺩ.ﺇ506 per night

Guest favorite

Barn in Rensselaer

5.0 out of 5 average rating, 275 reviews

The Loft at Virgie

You don't have to be born in a barn to vacation in one. Trade in the city for millions of stars in the night sky! As you enter thru the French doors you will be greeted by an open concept room decorated with a barn/industrial motif. Knotty pine car-siding and galvanized steel, wood floors along with a reclining leather couch and love seat fill the room A full kitchen with granite counter tops await you. There is plenty of natural lighting for the evenings.

Jan 24 – 31

ﺩ.ﺇ557 per night

Guest favorite

Home in De Motte

4.96 out of 5 average rating, 207 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.

Oct 20 – 27

ﺩ.ﺇ407 per night

Guest favorite

Tiny home in Burr Ridge

4.92 out of 5 average rating, 239 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

Sep 29 – Oct 6

ﺩ.ﺇ408 per night

Guest favorite

Apartment in Lemont

4.96 out of 5 average rating, 23 reviews

Burr Oak

Nestled in the Palos Forest Preserve with access to many miles of hiking and biking trails . One bedroom 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.

Sep 22 – 29

ﺩ.ﺇ287 per night

Guest favorite

Apartment in Blue Island

4.93 out of 5 average rating, 264 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.

Oct 30 – Nov 6

ﺩ.ﺇ553 per night