Vacation rentals in Orland Park

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Quick stats about vacation rentals in Orland Park

  • Total vacation rentals

    Explore 20 vacation rentals in Orland Park

  • Nightly prices starting at

    Orland Park vacation rentals start at G$8,365 GYD per night before taxes and fees

  • Verified guest reviews

    Over 280 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Orland Park vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Orland Park rentals

  • 4.9 Average rating

    Orland Park stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated vacation rentals in Orland Park

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Superhost
A well-lit sleeping area features a cozy bed with soft linens and decorative pillows. Natural light filters through two windows, complemented by light-colored curtains. A wooden bench and a small desk enhance the space, while a stylish area rug adds warmth to the hardwood floor.
Apartment in Lockport
4.92 out of 5 average rating, 105 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 favorite
A modern living room features a brown, tufted sofa and two blue armchairs set around a decorative area rug. Natural light enters through a large window adorned with light curtains and a door nearby leads outside. Framed wall art decorates one side of the room.
Home in Frankfort
4.96 out of 5 average rating, 54 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

Superhost
Home in Country Club Hills
4.91 out of 5 average rating, 32 reviews

Cul De Sac Jacuzzi home | Near Chicago

✨ Unwind, Recharge, and Escape Near Chicago ✨ Looking for a relaxing getaway without traveling far? Our cozy retreat offers the perfect blend of comfort, entertainment, and relaxation—just 35 minutes from downtown Chicago. After a day of exploring nearby forest preserves, shopping, dining, or city attractions, sink into the private jetted tub and let the stress melt. Whether you're planning a romantic weekend, vacation, or just a getaway, this home is designed to help you relax and reconnect.

Superhost
A modern living area features a gray sectional sofa adorned with plush pillows. A sleek coffee table sits atop a light area rug. A large television is positioned against a wall, and a kitchen bar with three stools is visible in the background, showcasing a stylish kitchen layout.
Home in Lockport
4.87 out of 5 average rating, 55 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 favorite
Guest suite in New Lenox
4.87 out of 5 average rating, 23 reviews

The Blue Daisy - Charming Private Studio

Keep it simple and affordable in this peaceful and centrally-located studio apartment. Sleeps 4! Perfect for sports and business travelers. Fully functional with a queen-sized bed, plenty of closet & storage space, desk, full bathroom (shower), kitchenette, and a living space with a pull-out couch. Shared laundry. The private entrance to the space is off the home's well-lit back backyard patio. Safe & secure as the studio is locked from the main residence and security cameras are present.

Superhost
Home in Matteson
4.67 out of 5 average rating, 3 reviews

Creek Retreat on 1 acre | Game Room | Fire Pit

➜ Fully remodeled with stylish, modern finishes ➜ Private 1-acre lot, resort-style backyard in nature ➜ Peaceful creek with a private bridge & boardwalk ➜ Waterfall, fountain & fire pit ➜ Giant lawn checkers, & cornhole ➜ Pergola dining, multiple seating areas & gas grill ➜ Game room: pool table, foosball & board games ➜ Smart TVs in most rooms + fast Wi-Fi ➜ ~35–45 min to downtown Chicago; Metra, dining & casinos nearby ➜ A one-of-a-kind retreat to relax, reconnect & make memories

Superhost
Home in Worth
4.85 out of 5 average rating, 185 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.

Superhost
A corner jacuzzi whirlpool tub is positioned against a wall, featuring multiple jets for relaxation. A white toilet and a small wooden stool are visible nearby. Light gray walls are complemented by a window covered with a light-colored curtain, allowing natural light to filter in.
Home in Chicago Ridge
4.89 out of 5 average rating, 206 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.

Superhost
Home in Matteson
4.84 out of 5 average rating, 74 reviews

5-BR Home: 1.5-Acre Yard & Fire Pit

Welcome to your private oasis! - Spacious open concept with 5 bedrooms and 2 bathrooms. - Cozy downstairs living room with a wood-burning fireplace and lounge area. - Expansive backyard featuring BBQ grill, fire pit, and direct access to Butterfield Creek. - Large two-car garage and abundant parking space for guests. - Relax in nature on 1.5 acres while being minutes away from shopping and dining.

Top guest favorite
A cozy bedroom features a comfortable bed with a quilted cover and decorative pillows. A colorful textile art piece depicting Route 66 is displayed on the wall. A side table with a lamp adds to the charm, complemented by a vintage photograph hanging above.
Home in Lockport
4.96 out of 5 average rating, 188 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 favorite
Home in New Lenox
4.86 out of 5 average rating, 7 reviews

Relaxing Home Away From Home

Enjoy a relaxing stay with the whole family in this spacious, stylish home featuring 3 bedrooms and 4 full bathrooms. Plenty of room to spread out, plus a 2-car garage and private driveway for easy parking. Located in a quiet area just minutes from downtown New Lenox, close to shops, dining, and conveniences. Clean, comfortable, and thoughtfully designed for a stress-free stay.

Top guest favorite
A ranch-style home is showcased with a welcoming facade of brick and siding. Large windows provide ample natural light, while a well-maintained garden features a variety of colorful flowers. A manicured lawn and sidewalk lead to the entryway, enhancing the inviting exterior.
Home in Worth
4.94 out of 5 average rating, 118 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 vacation rentals

When is the best time to visit Orland Park?

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Avg. priceG$43,078 GYDG$33,458 GYDG$31,367 GYDG$46,842 GYDG$57,088 GYDG$59,598 GYDG$52,906 GYDG$26,976 GYDG$26,767 GYDG$38,477 GYDG$33,667 GYDG$48,724 GYD
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Frequently Asked Questions

  • What are the best places to stay in Orland Park?

    Visitors often stay near the village’s shopping districts or in quiet residential neighborhoods close to parks. These areas make it easy to access local attractions and dining.

  • What are the best things to do in Orland Park with kids?

    Kids enjoy exploring Centennial Park’s play areas, splashing at the aquatic center, and skating at the nearby rink. Indoor adventure zones and local libraries are also frequently suggested for families.

  • What are some of the best things to do in Orland Park?

    Explore trails at Orland Park Nature Center, enjoy parks, or catch a show at the local cultural center. Shopping and dining at the village’s bustling mall area are also often recommended.

  • How is the weather in Orland Park?

    Orland Park has cold winters with temperatures as low as 19°F (-7°C), and warm summers reaching around 85°F (29°C). Rain is spread throughout the year, and the area sees snow and seasonal shifts, so packing for varied weather is wise.

  • When is the best time to visit Orland Park?

    Late spring through early fall is often recommended, when temperatures are milder, flowers bloom, and outdoor events take place. Winter has a distinct character, with snow and festive community traditions.

  • What are the best places to visit in Orland Park?

    Many enjoy Centennial Park for its scenic lake and recreation facilities, as well as the Orland Park Nature Center for quiet trails. The local mall is popular for shopping, dining, and indoor entertainment.

  • What are some hiking trails in Orland Park?

    Orland Park has walking paths at Centennial Park and scenic trails at Orland Grassland, where you can experience native prairie landscapes. The village’s nature centers also feature loop trails suited for various ages and abilities.

  • What are some family activities we can do in Orland Park?

    Families often explore Centennial Park with its playgrounds and walking paths, or cool off at the nearby aquatic center in warmer months. Indoor play spaces and bowling alleys around the area add more options for a fun-filled day.

  • What are some of the best day trip ideas from Orland Park?

    Visitors frequently explore nearby forest preserves for hiking and wildlife, or travel toward Lake Michigan for beaches and museums. Historic sites in surrounding towns add depth to a day’s itinerary.

  • Are there any pet friendly accommodations available in Orland Park?

    Many vacation rentals and some neighborhood stays in Orland Park welcome pets. Parks and several recreational trails make it easier for visitors to explore with their dogs.

  • What are some local tips for visiting Orland Park?

    Orland Park has several nature trails; comfortable walking shoes help you experience them fully. Locals suggest layering clothing in case of changing temperatures, and sampling a mix of locally owned and global cuisine throughout the neighborhoods.

  • What is Orland Park known for?

    Orland Park is known for its expansive parks, vibrant shopping districts, and community festivals. The area draws visitors with its recreational trails and diverse local dining options.

  • What are the best hidden gems to explore in Orland Park?

    The Orland Grassland preserve has peaceful walking trails where prairie landscapes and local birds can be spotted. Art displays tucked inside the civic center, and small family-run bakeries, frequently surprise visitors.

  • What are the best foods to try in Orland Park?

    Locally, pizza and classic Chicago-style hot dogs are often suggested, along with global cuisine ranging from Mediterranean to Asian flavors. Bakeries and small diners bring distinct homemade treats to the community’s food scene.

  • What should I bring for a trip to Orland Park?

    Pack layers, a waterproof jacket, and sturdy shoes—winters can be brisk with snow, while summers are warm and humid. Bringing a reusable water bottle and sunscreen helps for outdoor activities.

  • What is the nightlife in Orland Park like?

    Orland Park’s nightlife focuses on casual lounges, sports bars, and live music in local pubs. Many gather at spots with outdoor seating during warmer months, and some venues host trivia nights or dancing.

  • What are the most popular events or festivals in Orland Park?

    Orland Park has seasonal festivals and farmers markets, with outdoor concerts commonly held in summer. Community celebrations around national holidays, like Independence Day and Labor Day weekend, often draw visitors.

  • Are there family friendly vacation rentals in Orland Park?

    Orland Park has family-friendly vacation rentals that include amenities like full kitchens, multiple bedrooms, and easy access to parks. Neighborhoods near community centers and schools are popular among families.