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Vacation rentals in Orland Hills

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Orland Hills

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
4.97 out of 5 average rating, 37 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
A spacious living room area is displayed, featuring a large flat-screen TV mounted on a wooden accent wall. A modern dining table with dark chairs stands at the forefront, complemented by a decorative plant and round mirror nearby. Soft lighting is provided by recessed ceiling lights.
Apartment in Lockport
5 out of 5 average rating, 22 reviews

Lockport Farmhouse: King Bed + Parking by Door

Discover your ideal getaway in our charming Lockport, Illinois, Airbnb! This inviting retreat features a full kitchen with stainless steel appliances, a large bedroom with a massive king bed, a coffee bar for your morning brews, and tons of sunlight! Unwind in the large living room and watch your favorite shows on the 55-inch Roku TV. Enjoy the convenience of a shared on-site laundry room. Experience the perfect mix of modern comforts and rustic charm in Lockport. Secure your booking today!

Top guest favorite
A decorative tray is displayed on a neutral-toned couch, featuring a white vase filled with faux white foliage and a black candelabra holding two tall white candles. A wall art piece and a green plant can be seen in the background.
Townhouse in Orland Park
5 out of 5 average rating, 28 reviews

Luxurious townhome 30 days lease open for1-2 weeks

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. Please red carefully. Village of orland park has rules of 30 days minimum required lease with crime free housing addendum to be signed.

Guest favorite
A comfortable living area features a patterned sofa and armchair, positioned near a decorative fireplace. A small table is set with items, while a dining area is visible in the background. Natural light enters through the window, enhancing the cozy ambiance.
Apartment in Lemont
4.86 out of 5 average rating, 83 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.

Guest favorite
A modern kitchen features sleek white cabinetry and stainless steel appliances. A central island serves as a dining space, complemented by two navy blue stools with gold accents. Pendant lights provide illumination, enhancing the contemporary feel of the room.
Home in Chicago
4.88 out of 5 average rating, 161 reviews

Boho Chic Coach House 30Min to downtown W/ Parking

Whether your looking to stay near family or be close to Downtown. This place has it ALL! This coach house is located in Mt greenwood which is one of the safest neighborhoods in the City of Chicago. It is home to many police, firefighters and teachers. Downtown is a quick 30 minute drive and there are also many bars and restaurants in walking distance. The home has been totally renovated and stocked with all the essentials. All you need to do now is pack your bags and enjoy your vacation.

Top guest favorite
A cozy tiny home is situated beside vibrant organic vegetable fields, showcasing rows of leafy greens. The home features a combination of rustic wood and modern metal siding, with large windows and a welcoming porch area that includes chairs for outdoor relaxation.
Tiny home in De Motte
4.93 out of 5 average rating, 129 reviews

Tiny Home on Organic Veggie Farm

Place yourself right in the beauty of the land and nature in this cozy tiny home at Perkins' Good Earth Farm. The tiny home has a loft bedroom, bathroom with shower and composting toilet, kitchen, sitting area, and deck. You'll be surrounded by organic vegetable fields, 11 acres of woods, walking trails--and within perfect view of both the sunrise and sunset. You'll also have easy access to our farm store where you'll find fresh fruits & veggies, homemade soups & salads and so much more.

Top guest favorite
A sitting room features a beige sofa and a cream-colored armchair, positioned near a wooden desk. Two lamps provide soft lighting, while several framed photographs and artwork adorn the walls. Large windows allow natural light to fill the space, complemented by neutral-colored carpeting.
Guest suite in Orland Park
4.97 out of 5 average rating, 112 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 favorite
A spacious studio unit is showcased with exposed brick accents and hardwood flooring. A neatly made bed with light bedding is positioned near large windows, allowing natural light to fill the room. A dining area with three brown leather stools and a kitchenette is visible to one side.
Apartment in Frankfort
5 out of 5 average rating, 16 reviews

Studio 2B at The Kreger House

Stay in the heart of historic downtown Frankfort! This second level unit is situated in the Hallmark suburb of Frankfort. It is located in an immaculately restored 1863 building just steps away from fine dining, walking trails, parks, shopping, and quality entertainment. This upscale studio style unit has been completely restored. It features high end finishes throughout such a custom shower and heated tile bathroom floor. Come relax and enjoy Historic Frankfort!

Top guest favorite
Private room in Alsip
4.9 out of 5 average rating, 260 reviews

Safe clean charming close transportation Viva!

Hello world, The room is called la Dolce room, Inspired by my trip to Italy Rome The rug is like a fancy cake top , dark brown for tiramisu dessert, the walls is the color of cappuccino coffee ice cream, & some art Decour made to put you in sweet dream mode in a queen size bed. A beautiful Clean bathroom with clean linen to refresh your self. Have a second room for office space, to use a desk. Safe parking for your rental, close to the highway

Top guest favorite
Private room in Oak Forest
4.97 out of 5 average rating, 286 reviews

Cozy Cove on Chestnut

You will enjoy a private space with a private entrance on the lower level of our home located in a family oriented neighborhood. We are conveniently located near two Metra stations for easy travel into the city. We are less than 10 minutes away from the Hollywood Casino Amphitheatre, among other entertainment venues. We are lucky to have many neighborhood fests nearby such Gaelic Fest, Carribean Block party, RidgeFest, and many more.

Guest favorite
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
4.91 out of 5 average rating, 169 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.

The exterior of the home is displayed, featuring a welcoming entrance with a centered front door flanked by large windows. A well-maintained lawn and landscaped garden surround the home, with carefully arranged stones and shrubs leading to the entry. Trees offer shade in the yard.
Home in Orland Park
4.8 out of 5 average rating, 15 reviews

New! Modern Retreat with Private Pool & Yard

Discover the perfect blend of comfort and convenience at this stylish Orland Hills getaway! This spacious vacation home features a private backyard oasis complete with a sparkling pool, perfect for relaxing summer days or entertaining the family. The fully fenced yard offers both privacy and peace of mind, whether you're enjoying a quiet morning coffee or an evening cookout.

Popular amenities for Orland Hills vacation rentals

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