Holiday rentals in Highland

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Top-rated holiday rentals in Highland

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

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Guest favourite

Flat in Hegewisch

4.9 out of 5 average rating, 215 reviews

Handicap accessible apartment w/Level-2 EV Charger

Just 12.5 miles from downtown in the extremely quiet Chicago neighborhood of Hegewisch. Walking distance to the South Shore train line, which can easily get you to Chicago museums and entertainment, or attractions in NW Indiana. Private parking in back also gives you the option of driving anywhere and then walking directly to your door, and outside cameras are present for security. Banks, restaurants, grocery, convenience, and liquor stores are all 1 block of the apartment for all your needs.

Guest favourite

Home in Lansing

4.79 out of 5 average rating, 126 reviews

Cozy at The Walter

Just 35 minutes from Downtown Chicago Center in a quiet residential area. Close proximity to I-94 & I-80 ! 52 mins from Ohare Airport & 40 mins from Midway Airport-In normal traffic drive. Smaller Home(854 sqft) - Perfect for a Business Traveler, Couple, or Single person seeking a Private Uninterrupted Accommodation. Indiana state line > 1 mile ( 4 casinos within 20 minutes-often shows & events),Local restaurants & breweries, Shopping, Trails, Golf courses( Ravisloe Golf Club & Centennial).

Superhost

Cottage in Merrillville

4.87 out of 5 average rating, 246 reviews

The Hideaway

This Christian friendly cozy cottage, located 30 minutes from Chicago is located on a private 3 acre property. It’s a private detached cottage from main house that sleeps four. One king size bedroom (2 air mattresses) (sheets supplied), large full bathroom with deep tub w/ handle (towels supplied), full kitchen (dishes, pots and pans ect supplied) private covered parking and yard (directly in front of cottage) w/ its own fire pit for enjoyment. No plug for electric cars (station 2 m away).

Top guest favourite

Cottage in Gary

4.95 out of 5 average rating, 176 reviews

Neon Dunes Vista Beachfront Cottage

Neon Dunes Cottage is perfect for a romantic getaway. A newly renovated cottage with new kitchen, modern appliances and new bathroom all in a bright airy home. It is located in Indiana Dunes National Park/Miller Beach. Only 1.5 blocks to the beach, you can hike trails nearby and come back to relax in a unique, comfortable setting with ambiance and charm. It's perfect for summer/holidays. Wifi, onsite parking and self check in, allow you to enjoy our wonderful home in privacy and peace.

Guest favourite

Flat in Hammond

4.84 out of 5 average rating, 149 reviews

Plant MOOD FREE Wi-fi, parking, washer & dryer!

LATE CHECK-IN guest are welcome!!!! PLEASE READ MY FULL AIRBNB LISTING PRIOR TO BOOKINGS!!!! 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!

Superhost

Home in Hammond

4.77 out of 5 average rating, 57 reviews

Cozy, King/Queen bed, 2 bedroom.

UPDATE: Central Air unit installed 5/2025!! You can forget your worries in this spacious and serene space. Located in Hammond Indiana, just 40-45 mins drive to downtown Chicago. Get where you need to go safely and worry-free. This home is located 5 mins from the nearest Interstate and 10 mins from the train station. Plenty of thoughtful detail was given to ensure that you enjoy your stay. My hope is that you enjoy this space as I have for many years.

Top guest favourite

Home in Highland

4.96 out of 5 average rating, 24 reviews

2 King 1 Queen + Office Guest Suite

• Weekly & Monthly Discounts • 40min to Chicago Grant Park/Pier • Near Hard Rock, Wolf Lake, Indiana Dunes, Casinos, Purdue University Northwest • Tons of Shopping & Restaurants on nearby Indianapolis Blvd (41) • Close to 94, 41 and 912 • Very Safe/Quiet Neighborhood • Office/Guest Room w/separate entry door • Fenced-in side/back yard • Attached 1 car garage • New Kitchen & Baths • New HVAC • Memory foam gel, plush mattresses • USB charging ports by beds

Top guest favourite

Home in Munster

4.94 out of 5 average rating, 104 reviews

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.

Top guest favourite

Guest suite in Crown Point

4.93 out of 5 average rating, 242 reviews

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.

Guest favourite

Guest house in Merrillville

4.92 out of 5 average rating, 110 reviews

Romantic Getaway Guesthouse/ Jacuzzi/Sauna/Pool

Romantic Getaway | Private Suite w/ Jacuzzi, Sauna, Pool & Gym Indulge in a luxurious, private retreat designed for couples! This beautifully styled guesthouse/in-law suite offers ultimate relaxation with a private entrance, spa-like 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.

Superhost

Home in Gary

4.91 out of 5 average rating, 79 reviews

Laurna Dune

Welcome to Laurna Dune, your 2 bedroom carefree get away! Seamless checkout, no clean up required. Cute modern farmhouse decor in a quiet, friendly neighborhood, comfortably furnished with everything you may need! Located 2 minutes from the Hard Rock Casino with convenient access to the expressway, train, and airport. 15 minutes to just about anywhere you want to go!