Holiday rentals in Orland Park

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Top-rated holiday rentals in Orland Park

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Top guest favourite

Flat in Lockport

4.96 out of 5 average rating, 73 reviews

Full Kitchen, Near Hwy, Parking Nearby, Work Desk

Experience tranquility in this charming Lockport studio, blending vintage charm with modern comforts. The studio offers a cozy queen-size bed, premium amenities, and a smart TV. The sunlit kitchen, equipped with sleek appliances and a delightful coffee nook, invites culinary adventures. Step into the vast backyard, a serene haven for relaxation or play, complete with laundry facilities for convenient living. Located on Archer Ave, enjoy easy access to I-55 and I-355. Your perfect retreat awaits!

Top guest favourite

Home in Lockport

4.96 out of 5 average rating, 137 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

Flat in Worth

4.75 out of 5 average rating, 12 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.

Guest favourite

Flat in Lemont

4.91 out of 5 average rating, 68 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.

Top guest favourite

Guest suite in Geneva

4.99 out of 5 average rating, 659 reviews

A Suite within a Cozy cottage in Geneva Illinois.

Cozy private suite in the lower level. Guests have the suite to themselves. The bathroom is adjacent to the room and is private. There is a small fridge, a coffee maker, and a microwave oven. We are in Geneva, Illinois. We are LGBTQ+friendly. Our space is ideal for shorter stays and visitors on the go . Not suitable for staycations. Quiet area. Hosts live on the upper level and guests pass through our space to get to the suite. In a bind we can accommodate a 3rd guest and a pet. Welcome.

Top guest favourite

Flat in Aurora

4.99 out of 5 average rating, 155 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

Guest suite in Orland Park

4.98 out of 5 average rating, 98 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.

Top guest favourite

Yurt in Homewood

4.97 out of 5 average rating, 109 reviews

Glamping Yurt&RV-Game Room-Pool-Sauna-Hotub Court

Glamping Experience to the NEXT LEVEL! Opened April - Nov. Contact during off season. Mini Resort Includes: RV w/bathroom - 2 beds & sofa sleeper 20' Safari Yurt - 4 beds w/sofa sleeper Game Room w/bathroom 1 bed & sofa sleeper Gazebo w/2 twin beds Outdoor wooden Barrel-Sauna 27' above ground Pool 6-7 Person outdoor hot-tub Fresh Eggs seasonally Mini Golf lanes Basketball, Volleyball, Pickleball court Breakfast included is 1 dozen fresh eggs!

Guest favourite

Tiny home in Burr Ridge

4.9 out of 5 average rating, 377 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

Flat in Blue Island

4.94 out of 5 average rating, 298 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

Home in Chicago Ridge

4.92 out of 5 average rating, 139 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

Townhouse in Orland Park

5 out of 5 average rating, 26 reviews

Luxurious townhome

Welcome to our charming home in Orlando park- Ideal for both leisure and work. This comfortable house offers a perfect blend of relaxation and convenience. Located in a very safe and family-friendly community with numerous shopping plazas, restaurants, and activities. Only 30 minutes from Chicago's Midway airport and 3 minutes to the closest train station.

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Popular amenities for Orland Park holiday rentals

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Free parking on premises

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Other great holiday rentals in Orland Park

Guest favourite

Private room in Willow Springs

4.93 out of 5 average rating, 278 reviews

Private bedroom A in a quiet Chicago suburb.

RodrigoRating, 5 stars1 week ago

Had a nice time, was flexible about parking spots.

Top guest favourite

Home in Berwyn

5 out of 5 average rating, 13 reviews

The Architectural Haven - 15 min from Chicago!

TiffanyRating, 5 stars2 days ago

Stop looking and start booking‼️ This place is everything❤️the hosts are amazing. Me & my 5 sisters & photography enjoyed this place so much it was cozy, safe, clean, spacious, & well designed. We felt right at home. If you looking for a place look no further this is the best choice.

Guest favourite

Home in South Holland

4.77 out of 5 average rating, 26 reviews

Romantic Guest Favorite | Couples' Escape

AlexisRating, 5 stars1 week ago

Nicole was very helpful and friendly. Her place was clean and looked like the pictures posted. I would definitely recommend this listing.

Home in Homewood

4.88 out of 5 average rating, 40 reviews

The executive suite

GustavoRating, 5 stars1 week ago

The place was very nice if I come back to Chicago I will definitely be staying here again!

Guest favourite

Private room in Richton Park

4.85 out of 5 average rating, 241 reviews

Urbal retreat

RobertRating, 5 stars1 week ago

The host was great, we loved the cozy room and amenities. The shower was very clean and nice. Great spot for if you’re just passing through.

Cabin in Mokena

4.7 out of 5 average rating, 33 reviews

Gorgeous Log Home in Chicagoland!

PamelaRating, 5 stars3 weeks ago

My family stayed there for a long weekend. They said it was beautiful, clean and plenty of room for the six adults and one two year old.

Guest favourite

Private room in Woodridge

4.86 out of 5 average rating, 499 reviews

Private floor with Bedroom, bathroom, living rm

NecoleRating, 5 stars4 days ago

Taylor's place was very nice; she really thought of everything. Everything you could need was there; Taylor makes you feel right at home. The neighborhood is nice and you're close to a number of things. Oh and the shower pressure was great!

Guest favourite