Vacation rentals in Chicago Heights

Luxury 4BR w/ Spa Tub Near UChicago & Obama Center

Discover Metra Haven, a luxury thoughtfully designed 4BR near Hyde Park, this home is ideal for bachelorette weekends, girls trips, family gatherings, professionals or large groups seeking cozy comfort Unwind in the spa-style bath tub, gather in the private backyard patio, with fire place for cozy evenings accommodating your group Steps from Metra station with a direct train to Downtown, 4mins away from the Obama presidential center in Jackson pack, museum of science & industry and the lake

The Ashlin House.

Stay at our family-friendly home on a quiet, cobblestone street on vacation or business. We've recently repainted the exterior and painted the master BR. Walking distance to quaint Downtown Whiting , Lake Michigan, Whihala Beach & Lakefront trails. The Horseshoe Casino, Wolf Lake & Pavilion, Hammond Sportsplex, Calumet College, PNW, IUN, U of Chicago, BP, & golf courses are a short drive. See Chicago's Skyline at Lakefront Park. Chicago's attractions & Hard Rock Casino are < 30 mins away.

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.

Home in Richton Park, Illinois

3 bedrooms: 1 King, 2 Queen size 4K Flat screen TV’s each bedroom 40 min to Chicago Fully Stocked kitchen w/ Coffee Tea & Hot Chocolate Station Microwave, Dishwasher, Oven Range, Refrigerator w/Ice maker, Stainless Steel Farm Sink. Elegant Living Room & Dining Combo 65" TV with Streaming Central Air/ Outdoor Mini Deck Full Bath w/ Glass Shower Doors 1 work space. Game Room w/ TV & Laundry Room Wi Fi included, NO PETS, NO PARTIES, NO SMOKING🚭 in unit or on deck PET FINE $500

Fun game-room suite with hot tub & optional Yurt

Activities includes: PS5 Disc w/TV Xbox Series X w/TV Outdoor heated Jacuzzi 27' above ground pool Pool and Air hockey table Arcade machine with 12 games Life Size Connect 4 Board games Basketball machine Electric fire place Queen & full size beds Full size sofa pull out sleeper Gazebo with two twin beds (seasonal) Fresh Eggs with chickens seasonal Gas Grill-propane included Romantic Robe for 2 (in colder months must request) Event Yurt add on $225 up to 25 additional guest

Homewood Oasis

Welcome to our Homewood Oasis, where relaxation meets family fun! As former residents of this charming town, we know the importance of a comfortable and enjoyable stay when coming back to visit. Our Airbnb is more than just a place to sleep; it's a carefully curated space designed for families like yours. As hosts who've experienced the need for a home away from home, we've put our heart into making this space welcoming and enjoyable for you. We look forward to hosting you!

Cozy & Lavish 2B/1B in Homewood!

Our Peaceful, Kid-friendly, and Centrally-located Duplex sits in the heart of Downtown Homewood. The choice of a 30 min drive or 7 min walk to the Metra going to Downtown Chicago awaits you! You can enjoy this vacation home while exploring the beautiful city! Our new Casino welcomes you! Enjoy the convenience of free parking, nearby pool club, skate park, shopping markets, walkable parks, and quick access quick to freeways. Long-Term Travel Stays are Welcomed!

Cottage Feel 2 bedroom Home!

Welcome to your home away from home! Relax and unwind in this cozy, peaceful space that’s thoughtfully maintained to make your stay comfortable and stress-free. While this isn’t a luxury home, it’s clean, inviting, and equipped with everything you need for a pleasant visit. Conveniently located in the south suburbs of Illinois, you’ll be just minutes from great restaurants, shopping, parks, entertainment, and major highways.

Quiet Oasis: Cozy, Private, Fenced Yard & Office

Private, pet-friendly 2-bedroom single-level retreat near Chicago, ideal for 4 guests + infant. Features a dedicated remote workspace with 413 Mbps Wi-Fi, fully equipped kitchen, and a spacious private backyard with a gas grill. Perfect for remote workers, cycling enthusiasts, and brewery lovers, offering easy access to nature trails, 6 local breweries, and casinos. Enjoy a quiet escape just 30 minutes from the city.

Two Bedroom Apartment Walk to Metra

Cozy private lower-level apartment in Homewood, just a 5-min walk to the Metra for easy access to Chicago. Features 2 bedrooms (king & queen), pullout sofa, 2 full baths, and seating for 6. Enjoy a backyard fire pit and full front driveway parking. Walk to a playground, with a skate park across the street and the casino just a short drive away. Quiet, comfortable stay in a convenient location.

Escape to relax in peace

Reconnect with nature at this unforgettable escape nestled on a working 82 acre family farm. Upon arrival you will receive fresh eggs from our free range chicken eggs and honey from our honey bees . You might see Casey our farm manager from Poland. He takes care of the animals daily. Enjoy the fire pit and a barbecue for dinner while star gazing at night. Then rest in peace.

Romantic Escape ~ Adult Playhouse w Exotic Dungeon

“What a great time we had, reconnecting and enjoying each other. We came back home in such a better place than we where when we left.” 🌹More than a stay — a private, immersive romantic experience crafted exclusively for adult couples who want something unforgettable, intimate, and truly one-of-a-kind.