Vacation rentals in Highland

Lakeside Dome Retreat w Hot Tub Near Indiana Dunes

Welcome to Valparaiso Lakeside Retreat a private getaway on Long Lake featuring a one-of-a-kind outdoor geodesic dome (11 feet), hot tub, fire pit, & kayaks. 20 minutes from Indiana Dunes National Park. Perfect for couples, remote workers & nature lovers seeking a tranquil escape. Enjoy stunning Long Lake views from your private backyard & dome. Long Lake public beach access is just around the corner. Perfect for kayaking, swimming, or a morning walk to the water. Book this unique stay today!

Couples Getaway, Jacuzzi, Sauna, Pool is Open

Couples Getaway | Private Suite w/ Jacuzzi, Sauna, Pool & Gym Indulge in a luxurious, private retreat designed for couples! This beautifully styled guesthouse suite is attached to the main house but completely private—you’ll have your own private entrance for total seclusion. Enjoy spa-like relaxation with a jacuzzi, sauna, pool access, and a fully equipped gym. Perfect for honeymoons, anniversaries, or weekend escapes, our space blends comfort, privacy, and elegance for an unforgettable stay.

1Plant MOOD FREE Wi-Fi Street Parking Washer/Dryer

PLEASE READ THE ENTIRE LISTING BEFORE BOOKING! LATE CHECKINS! Enjoy FREE Washer/Dryer Full Kitchen/STREET PARKING! This special place is close to everything, making it easy to plan your visit. • I80, 294, 94 highways/tolls, etc. • Chicago • Shopping galore • A fun array of restaurants AND A LOT OF FREE PARKING! I’m extremely close to MUNSTER, HIGHLAND, SCHERERVILLE, DYER and many more Indiana locations! I’m extremely close to LYNWOOD, LANSING, CALUMET CITY, and many more Illinois locations!

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.

La Petite •Piano•Serene Organic•Long Stay Discount

Welcome home to the heart of Merrillville — where everything you need is right at your fingertips. Minutes from South Lake Mall, great restaurants, and hospitals, with the South Shore Line just 10 miles away. Unwind in the second living area overlooking the surrounding greenery, or enjoy the open space of your private backyard. With a fully equipped kitchen, quiet neighborhood, it's easy to decompress the moment you walk through the door. DM us to plan your stay!

Cozy three bedroom home in Munster , Indiana.

Plan your next escape to Indiana or Illinois and stay in this beautifully renovated and thoughtfully appointed 3 bedroom and 1 bath home. Located in the quiet and safe suburb of Munster, Indiana, the property is just a 3 minute, easy access to the I-94 Highway. Exciting Downtown Chicago is just 30 minutes away! Walk to Riverside Park and take in the scenic view while enjoying a morning croissant and coffee from one of the quaint neighbourhood cafés.

IT'S THE WRIGHT PLACE

Private guest house newly remodeled. One bedroom queen bed, bath w/shower, full kitchen stocked, including microwave and Keurig coffee maker pods included, family room TV, and WIFI. No matter if you are in town for work, sport competition, family or just vacationing we offer all the comforts of home. Air Mattress available upon request. Please treat as your own home, follow all house rules. No party or gatherings. This is a no smoking home.

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.

Dunes Escape

Stay at Dunes Escape! This newly renovated 3 bedroom, 1 bathroom home comfortably sleeps 6 and is professionally staged and designed for short-term rental guests. Extend your stay and enjoy your “work at home” space! We offer full access to the home and backyard, where you will find a patio, charcoal grill, and a large fire pit area for you to gather.

Comfy 3BR 2BA, Liv+Fam Rm, Prime, 3-Car Parking

Welcome to your home away from home! Whether you're visiting for business, a family vacation, or a weekend getaway, this home offers the perfect blend of comfort, convenience, and relaxation. Everything is thoughtfully set up to ensure a smooth and enjoyable stay. Book your stay today and make yourself at home!

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.

Farm Themed Guesthouse!

Take it easy at this unique and tranquil getaway. You will be situated on a small hobby farm including livestock with a fishing pond and private deck! 5 minutes to Hard Rock Casino and 25 minutes from Chicago. I have equipped this home with everything you should need for a comfortable at home like stay.