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$8,367 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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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

Guest favorite
Home in Homer Glen
4.76 out of 5 average rating, 68 reviews

Homer Glen 5 bedroom home/ Close to Chicago

30 mi from Chicago. Close to Lemont, Orland , Lockport. 5 bedrooms, 2.5 baths, kitchen fully equip, family rm, living rm & fenced yard with grill. There are 2 king size beds, 3 queen sized beds as well as a baby portable crib. One bedroom is on main floor. Uber accessible in this area. Warning the home is not child proof, many items at child's reach. When the property is not rented this is our residence. NO PARTIES AS THIS IS IN A VERY QUIET NEIGHBORHOOD AND TOWN ORDINANCES ARE VERY STRICT.

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
4.88 out of 5 average rating, 58 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
A spacious living area is furnished with a large gray sectional sofa, accented by a black ottoman in the center. Natural light filters through the vertical blinds of two windows, while a round mirror adds a decorative touch to the wall.
Home in Tinley Park
4.91 out of 5 average rating, 33 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!

Guest favorite
Home in Tinley Park
4.82 out of 5 average rating, 38 reviews

Cozy/Private 3 BR nestled on an acre of Serenity

Freshly renovated 3 BR/1 Bath home with modern furnishings and serenity all around. Enjoy this private, cozy home nestled amongst the trees and guarded with private entry for a relaxing stay. Located less than a 1/4 mile from I80 give you easy access to all of Chicagoland . Enjoy the quaintness of Downtown Tinley Park and all of the vibrant shopping, cuisine and more it has to offer. Explore the big city and then come home to a park like retreat which offers seclusion and tranquility.

Guest favorite
Home in Matteson
4.8 out of 5 average rating, 5 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

Top guest favorite
A spacious dining area features a large wooden table with comfortable upholstered chairs, accommodating multiple guests. An elegant light fixture hangs above, providing soft illumination. The room connects seamlessly to the living area and kitchen, enhancing the open-concept design.
Bungalow in Beverly
4.96 out of 5 average rating, 45 reviews

Beverly Hills of Chicago Luxury Guest Favorite

Escape to luxury in this beautifully designed 5 bedroom, 3.5-bath home in Chicago's prestigious Beverly Hills neighborhood. Spacious living and high-end finishes, full finished basement have fun with air hockey, pool table, and video gaming, this entertainment space is for guests of all ages. Unwind on the private deck or enclosed front porch. explore retail shops and upscale dining. Metra train station provides a quick 15 minute downtown Chicago area. Close to downtown Chicago!

Superhost
Home in Worth
5.0 out of 5 average rating, 9 reviews

Modern Ranch Retreat | Near Metra & Chicago

Whether you're visiting family, staying for work, catching a flight from Midway, or exploring Chicago, you'll feel right at home in this newly remodeled 3-bedroom, 2-bath ranch. Enjoy a bright modern interior, dedicated dining room, fully equipped kitchen, fast WiFi, in-home laundry, a 2-car garage, and driveway parking for 2 more vehicles. Located in a quiet neighborhood just minutes from the Metra and Midway Airport.

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, 207 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
4.83 out of 5 average rating, 75 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.

Guest favorite
Home in New Lenox
4.89 out of 5 average rating, 9 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, 120 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$43,088 GYDG$33,467 GYDG$31,375 GYDG$46,853 GYDG$57,103 GYDG$59,613 GYDG$52,919 GYDG$26,983 GYDG$26,773 GYDG$38,487 GYDG$33,676 GYDG$48,736 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.