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Vacation rentals in Orland Hills

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Top-rated vacation rentals in Orland Hills

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Condo in Hickory Hills

4.92 out of 5 average rating, 59 reviews

Convenient Location near ammenities. KING size bed

Walking distance to restaurants, stores etc. 1st floor suite will be your relaxing retreat. King size bed with a foam mattress, down pillow/comforter set, blackout curtains will allow you a restful sleep. BR is equipped with 2 side tables, 2 dimmable touch control table lamps with 2 USB Ports & AC Outlet. Bath offers a tub, vanity & open shelving. LR features faux leather sofa, coffee table w/the lift-top & 70” streaming TV. LR opens up to an eat in kitchen equipped with standard dine-ware.

Dec 7 – 14

G$18,957 GYD per night

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.

Apr 4 – 11

G$17,588 GYD per night

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!

Jun 24 – Jul 1

G$21,313 GYD per night

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

G$24,682 GYD per night

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.

Oct 24 – 31

G$27,836 GYD per night

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 25 – Feb 1

G$31,013 GYD per night

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.

Nov 11 – 18

G$22,651 GYD per night

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

G$23,145 GYD per night

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.

Oct 9 – 16

G$15,976 GYD per night

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.

Dec 13 – 20

G$28,787 GYD per night

Home in Manteno

4.97 out of 5 average rating, 113 reviews

Updated, bright, and modern, 3 bedroom home.

You will be comfortable in this newly remodeled three bedroom, two bathroom home. ✶ 6.7Miles to Olivet Nazarene University ✶ 8.4Miles to Riverside Medical ✶ 11Miles to Kankakee River State Park ✶ 43Miles to Midway Airport The home FEATURES: *Safe, quiet, walkable neighborhood *3 Bedroom; 1 King, 1 Queen, 2 twin beds *Spacious fully equipped kitchen with coffee station *Washing Machine, Dryer & Dishwasher * Fast Wi-Fi

Mar 5 – 12

G$30,907 GYD per night

Cottage in Merrillville

4.89 out of 5 average rating, 184 reviews

The Hideaway

This cozy cottage (lodging only, renters only) located 30 minutes from Chicago is located on a private 3 acre property. It’s a private detached cottage that sleeps four. One king size bedroom (sheets supplied), large full bathroom with deep tub (towels supplied), full kitchen (dishes, pots and pans ect supplied) and private parking. Also has its own fire pit for enjoyment.

Aug 13 – 20

G$20,560 GYD per night

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Popular amenities for Orland Hills vacation rentals

Free parking on premises

Air conditioning

Other great vacation rentals in Orland Hills

Home in Chicago

4.91 out of 5 average rating, 87 reviews

Boho Chic Coach House 30Min to downtown W/ Parking

Jan 8 – 15

G$23,827 GYD per night

Home in Chicago Ridge

4.9 out of 5 average rating, 49 reviews

Quiet cul-de-sac with huge fenced in backyard

Feb 3 – 10

G$30,885 GYD per night

Home in Robbins

4.97 out of 5 average rating, 36 reviews

Comfy Updated 3 Bdrm/2Bth -Near SXU, MVC & MDW

Sep 18 – 25

G$26,980 GYD per night

Camper/RV in Willow Springs

4.98 out of 5 average rating, 42 reviews

Wander Willow Springs Glamping Retreat

Oct 2 – 9

G$21,298 GYD per night

Home in Oak Forest

4.91 out of 5 average rating, 75 reviews

Cheerful three bedroom, 2 full bath in Oak Forest

Aug 13 – 20

G$57,011 GYD per night

Home in Homewood

4.91 out of 5 average rating, 35 reviews

Charming Homewood Away from Home

Aug 30 – Sep 6

G$29,771 GYD per night

Home in Lockport

5.0 out of 5 average rating, 36 reviews

Private Hideaway House Apartment

Jun 11 – 18

G$30,765 GYD per night

Home in Munster

4.97 out of 5 average rating, 34 reviews

Entire home: Private, Cozy Oasis in Quiet Locale

Apr 14 – 21

G$28,008 GYD per night

Destinations to explore