Holiday rentals in Highland

4.9 out of 5 average rating, 216 reviews

Flat in Hegewisch

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.

4.8 out of 5 average rating, 298 reviews

Home in Chesterton

South Shore Studio Apartment {National Park}

I have to warn you definitely not a hook up spot or party house!!! typically rise with rooster on this 5 acre country setting with a small fishing pond. 420 friendly .. Quiet hours are 11 -8 generally some music playing, musicians are welcome !! if you happen to book on a Sunday i host an Open Mic in my Barn every Sunday ..... pretty relaxed. Upon arriving, turn into the driveway, and then right into the yard. Apartment is upstairs, the door is open with the keys inside. ✌️

4.79 out of 5 average rating, 126 reviews

Home in Lansing

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).

4.87 out of 5 average rating, 247 reviews

Cottage in Merrillville

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).

4.95 out of 5 average rating, 177 reviews

Cottage in Gary

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.

4.84 out of 5 average rating, 149 reviews

Flat in Hammond

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!

4.77 out of 5 average rating, 57 reviews

Home in Hammond

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.

4.96 out of 5 average rating, 24 reviews

Home in Highland

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

4.94 out of 5 average rating, 105 reviews

Home in Munster

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 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 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.

4.91 out of 5 average rating, 79 reviews

Home in Gary

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!

Holiday rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Highland holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Highland

Home in Munster

4.64 out of 5 average rating, 14 reviews

Munster on the River

AlRating, 5 stars1 week ago

Great location and excellent neighborhood! The home is large with plenty of room to spread out!

Home in Gary

4.8 out of 5 average rating, 15 reviews

Holiday Homestead - Clean - Cozy - Comfort (4Bd)

DaisyRating, 5 stars2 months ago

Really enjoyed our stay at this location. It was very clean and described perfectly well. Left a pot behind and the host helped me find a solution to get my property.

Home in Gary

4.78 out of 5 average rating, 65 reviews

Relax city

CeshawannaRating, 5 stars2 weeks ago

The place was lovely and looked just like the pics, I recommend a 10/10.

Home in Merrillville

5 out of 5 average rating, 5 reviews

Spacious Serene Escape~ 20 mins IN Dunes

TymeenRating, 5 stars1 week ago

Amazing place me & my family visited for a wedding it was 6 adults & 2 kids plenty of space

4.89 out of 5 average rating, 47 reviews

Tiny home in Gary

Super Comfy Luxurious Tiny Home!

MontanaRating, 5 stars1 month ago

Cruz was a friendly host, checking in to make sure check in went smoothly and always very quick to respond. The place itself was very modern and clean. Would definitely recommend staying here.

5 out of 5 average rating, 5 reviews

Apartment in Munster

NEW 1bd/2bth 2 Story Condo in Quiet Neighborhood

KiaraRating, 5 stars4 months ago

I loveeeee this place.. carianne was very helpful and friendly . This place was so spotless, decore was perfect. felt right at home. Anything u might forget at home no worries, she has them. me and my spouse needed a weekend get away not to far from home this was perfect. we will for sure be staying here again 100000/10

4.98 out of 5 average rating, 53 reviews

Home in Munster

Cozy Farmhouse in Munster

JenniferRating, 5 stars2 days ago

A wonderful cottage, it was tucked away in a quiet neighborhood. The “home away from home”, was nicely appointed with furniture, linens, kitchen tools and utensils. The hostess was very responsive, helpful and friendly. Check-in was smooth and directions were clear. Beds were comfortable and we thoroughly enjoyed our stay. When we have an opportunity to be in the area again we will definitely see if this house is available! Till next time!