Holiday houses 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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Guest favourite
Apartment in Lockport
4.93 out of 5 average rating, 102 reviews

Fully Equipped Studio w/ Kitchen & Laundry Access

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 Frankfort
4.98 out of 5 average rating, 46 reviews

House in Frankfort quiet family neighborhood

Thank you so much for considering to stay at our home. My husband and I take extreme pride in being great hosts and providing a clean and comfortable home to stay in. We make sure to have everything you need to keep you comfortable so you can relax in your home away from home. I am extremely responsive so if you happen to have any questions, please do not hesitate to reach out. Relax with the whole family at this peaceful place to stay. 3 bedroom home newly remodeled and all new furnishings 2024

Guest favourite
A single-story ranch-style home is depicted, featuring a brick and siding facade. A two-car garage is positioned on the right side, with a well-maintained lawn and neat landscaping in the front yard. Clear skies and scattered clouds provide an inviting backdrop.
Home in Bolingbrook
4.92 out of 5 average rating, 155 reviews

Spacious Bolingbrook Retreat w/ Garage & Yard

Relax with the whole family at this peaceful and spacious 3-bedroom ranch home conveniently located near I-55 & I-355. Walking distance to Promenade Mall, restaurants, bars, shopping, Bass Pro Shop. Enjoy self check-in with smart lock, private attached 2-car garage, large backyard, patio, and grill. Perfect for families, work trips, or weekend getaways. Clean, safe, and only 30 minutes from downtown Chicago and major attractions. Self check-in Free parking Fast Wi-Fi Washer/dryer Backyard/patio

Guest favourite
A vibrant garden area is filled with a variety of lush green plants and colorful flowers. Stone elements lead to a small water feature, surrounded by dense foliage. The peaceful setting offers a natural retreat, inviting exploration or relaxation.
Apartment in Homewood
4.92 out of 5 average rating, 114 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 downtown Homewood to enjoy shopping & dining or catch the train to Chicago. 🏳️‍🌈 BLM Safe space! After a day of exploring, a king-sized sleep number bed & lush bathroom features will pamper you! A fold-down sofa creates an additional bed. Dogs welcome! This suite has a kitchenette with a convection toaster oven & induction cooktop.

Guest favourite
Home in Lockport
4.95 out of 5 average rating, 44 reviews

Stylish Lockport Home | King Bed + Coffee Bar

Welcome to your Lockport getaway! This spacious 3-bedroom, 2-bathroom home features a primary suite with a king bed and en-suite bathroom. Additional bedrooms come with queen beds. Gather in the stunning kitchen, showcasing a waterfall island with seating for three, stainless steel appliances, and a built-in wine fridge. Enjoy your morning brew at the fully stocked coffee nook with single-serve K-cups and a traditional carafe pot. Perfect for families or friends seeking comfort and style!

Guest favourite
Home in Tinley Park
4.91 out of 5 average rating, 23 reviews

Luxury Townhome in Tinley Park Near Shops & Train

Welcome to your luxury retreat in Tinley Park! This 3-level townhome features 3 spacious bedrooms, including a primary suite with en-suite, 2.5 bathrooms, a fully stocked kitchen, a large dining area, and an in-unit washer/dryer. Perfectly located near shops, restaurants, the Credit Union 1 Amphitheater, and just a short Metra train ride to downtown Chicago. Ideal for relaxation, business, or adventure—this space offers the perfect blend of comfort and convenience. Book your stay today!

Top Guest favourite
A spacious living area features a corner sectional sofa with soft cushioning and a cozy throw. Large windows provide natural light and city views. A simple coffee table sits in front, with light-colored carpet underfoot, enhancing the comfortable atmosphere.
Apartment in Aurora
4.98 out of 5 average rating, 254 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, 124 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
Home in Worth
4.86 out of 5 average rating, 176 reviews

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

This beautiful, newly remodeled, spacious, 3 bed 2 bath ranch style home is set back on a large lot. Located close to a major hwy, restaurants and a shopping. Just 15 minute to Midway Airport, 25 mins to O'Hare, and 25 mins to Downtown Chicago. Its a great spot to get to everything! Perfect for families, vacationers, and business travelers. You must be 21 or older to book. You must provide a valid photo of your D.L. or State ID upon request.

Top Guest favourite
Apartment in Warrenville
4.93 out of 5 average rating, 114 reviews

“The remote retreat”

We have a cozy one bedroom apartment that is available on the top floor of the home and has its own independent and separate entrance! Comes with free parking on premises; recently renovated; neighborhood is safe and quiet. Shopping center with grocery store, laundry mat and restaurant is available within walking distance! We are only 5 minutes from the expressway I-88 and 10 minutes from Naperville and the outlet mall in Aurora!

Top Guest favourite
Home in Lockport
4.96 out of 5 average rating, 175 reviews

Lockports Famous Hideaway ~ 2bdrm Guest House Flat

A history buff’s dream filled with antiques & artifacts relating to Chicago, Joliet, Lockport, the I & M Canal & "Route 66"! Family & Business Friendly. 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. Private-entrance/self-check-in. Have a 'historic' stay at the "Hideaway"! Can accommodate up to 6 guests.

Guest favourite
An outdoor patio area is featured, illuminated by string lights overhead. A hammock is suspended between two posts, offering a place to relax. Two comfortable chairs are arranged around a fire pit, situated on a lawn surrounded by tall hedges and trees.
Home in Worth
4.94 out of 5 average rating, 113 reviews

Worth It! 3 bedroom ranch home

Relax with the whole family at this peaceful place to stay. Just minutes from walking parks, outdoor concert venue, golfing, and down town! Comfy and inviting Ranch style home offers 3 bedrooms, a fully equipped kitchen, flat screen TVs, and large windows. The private backyard has a patio, and bbq grill. A real home away from home, we look forward to your new booking.

Popular amenities for Orland Park holiday rentals

When is the best time to visit Orland Park?

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Avg. price$347 NZD$270 NZD$253 NZD$283 NZD$310 NZD$320 NZD$426 NZD$217 NZD$216 NZD$310 NZD$271 NZD$393 NZD
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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Orland Park?

    Orland Park has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Orland Park?

    Experience the best of Orland Park with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Orland Park?

    Four-legged friends are welcome in Orland Park. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Orland Park?

    Yes! Work meets play with ease at over 10 vacation rentals in Orland Park featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Orland Park have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Orland Park. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Orland Park have a kitchen?

    Absolutely! We offer over 10 house rentals with a kitchen in Orland Park. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Orland Park have wifi?

    Absolutely! We offer over 10 house rentals with wifi in Orland Park. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Orland Park have free parking?

    Absolutely! We offer over 10 house rentals with free parking in Orland Park. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Orland Park

  • Total holiday rentals

    Explore 20 holiday rentals in Orland Park

  • Nightly prices starting at

    Orland Park holiday rentals start at $51 NZD per night before taxes and fees

  • Verified guest reviews

    Over 300 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Orland Park holiday rentals include Wi-Fi 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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