Vacation rentals in Highland

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Top-rated vacation rentals in Highland

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

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Top guest favourite

Home in Munster

4.94 out of 5 average rating, 86 reviews

Entire home: Private, Cozy Oasis in Quiet Locale

30 minute drive from Chicago's Grant Park. Near Little Calumet and Monon trails. Appeals to nature enthusiasts, cyclists, remote workers and brewery aficionados. This 2 bedroom, 1 bathroom retreat offers comfort and convenience. Full kitchen, private backyard and comfortable living space. 3 casinos, 6 breweries: 3 Floyds, 18th Street, Fuzzyline, Byway, New Oberpfalz & Wildrose within 7 to 20 min drive. Early check-ins offered/subject to availability. Feel free to inquire on availability.

Guest favourite

Home in Dyer

5 out of 5 average rating, 15 reviews

Chicago-ish Travels

If you want a cozy home in a quiet suburb fairly close to Chicago, this is a great option. 45 minute drive to downtown Chicago,(4 minute drive to train station that takes you downtown Chicago), 30 minutes from the Indiana dunes state park, and 5 minutes from the busiest street with plenty stores and restaurants in all of north west Indiana. A spacious townhouse to accommodate 6 people with one covered garage for one car plus space for two more uncovered spaces. No parties or gatherings.

Superhost

Cottage in Merrillville

4.87 out of 5 average rating, 251 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).

Guest favourite

Home in Gary

4.93 out of 5 average rating, 28 reviews

Hard Rock Haven!

Escape to this delightful house in the heart of Northern Indiana. Whether you're here on business, or just to relax this is the perfect place to escape the hustle and bustle of regular world. With 3 cozy bedrooms including 2 queen beds and 2 twin beds. The living room even offers 2 murphy beds for extra sleeping space. Enjoy the convenience of amenities like heating/AC, WiFi, Washer/Dryer, huge HD TV, Dog washing station, and covered back patio. Across the street from the Hard Rock casino!

Superhost

Apartment in Highland

4.76 out of 5 average rating, 17 reviews

Cozy Stays

Kick back and relax in this calm, stylish, 2bdrm apartment located just 25 minutes outside of Chicago. It’s on the 1st floor. . A very quiet community. Secured gated parking, Very convenient ‼️ Parking just steps away from the main door entry. Surrounded by nice restaurants, shopping centers, movie theaters, and workout facilities . A MUST SEE‼️ come savor the experience of a dwelling that feels very personal to your very own home. PRIVACY & CLEANSINESS IS TOP PRIORITY.

Guest favourite

Apartment in Hammond

4.85 out of 5 average rating, 157 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!

Guest favourite

Home in Highland

4.96 out of 5 average rating, 25 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

4.95 out of 5 average rating, 112 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.

Guest favourite

Guest suite in Crown Point

4.93 out of 5 average rating, 246 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

Guesthouse in Merrillville

4.92 out of 5 average rating, 118 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 Hammond

4.76 out of 5 average rating, 62 reviews

Cozy, King/Queen bed, 2 bedroom.

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.

Guest favourite

Townhouse in Munster

4.8 out of 5 average rating, 15 reviews

Townhome Near Munster/Hospital/BP Refinery

Duplex Home near the South Shore Line for a quick and easy commute to Chicago or close to all the hospitals and BP refinery. This place is intended for the corporate traveler. 30 night minimum stay required. Detached 2 car garage, fenced in yard, close to all the local restaurants and shopping, bike trail and park within walking distance.