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 favorite
A private outdoor gazebo houses a spacious jacuzzi, accompanied by soft lighting and a view of the surrounding greenery. Nearby, a wooden deck features a dining area with a table and chairs, inviting relaxation in a peaceful setting.
Guesthouse in Merrillville
4.94 out of 5 average rating, 158 reviews

Romantic Spa Getaway -Private 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 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.

Top guest favorite
Apartment in Hegewisch
4.91 out of 5 average rating, 238 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 favorite
A well-appointed bedroom features a spacious bed adorned with a soft blush and white blanket. A bedside lamp and decorative elements are present. Natural light filters through a window dressed with sheer curtains, creating a cozy ambiance. A small chair complements the interior design.
Apartment in Hammond
4.85 out of 5 average rating, 170 reviews

1Plant MOOD FREE Wi-Fi Parking Washer/Dryer

PLEASE READ THE ENTIRE LISTING BEFORE BOOKING! LATE CHECKINS WELCOME! Enjoy FREE Washer/Dryer Full Kitchen + MORE! 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!

Top guest favorite
A spacious living area features a light-colored sectional sofa adorned with soft pillows, positioned beside a wooden coffee table. A decorative area rug adds warmth to the hardwood floor. Natural light enters through a window, complemented by dark curtains. A potted plant and lamps provide additional light.
Home in Munster
4.95 out of 5 average rating, 110 reviews

Entire home: Private, Cozy Oasis in a 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.

Top guest favorite
The cottage exterior showcases a single-story structure with a light grey facade and a newly roofed design. Large windows allow natural light to enter, framed by a lush green landscape. A welcoming entryway leads to the home, complemented by garden pots and a gentle pathway.
Cottage in Gary
4.95 out of 5 average rating, 216 reviews

Neon Dunes Vista Beachfront Cottage

Neon Dunes Cottage is a one bedroom 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 favorite
A modern bathroom features a sleek white vanity with a single sink and gold accents. A separate shower area displays a smooth glass door and decorative tile inlay. A hair and makeup station with a chair is positioned nearby, along with towels hanging neatly on a rack.
Home in Highland
4.91 out of 5 average rating, 32 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 favorite
A charming single-story home is surrounded by lush greenery and colorful landscaping. The house features a light exterior with dark shutters and a welcoming front porch. A small tree adds a splash of color to the neatly manicured lawn.
Home in Munster
4.95 out of 5 average rating, 129 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 favorite
The exterior of a private guest house is shown, featuring a detached two-story structure. A driveway leads to a garage with a white door, while a wooden staircase ascends to the entryway. The surrounding area includes greenery and paved walkways.
Guest suite in Crown Point
4.94 out of 5 average rating, 263 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 favorite
A spacious living room is featured with a cream-colored sectional couch facing a mounted flat-screen TV. Natural light pours in through large windows adorned with blinds. A stone accent wall adds texture, complemented by two decorative pieces and a ceiling fan.
Home in Munster
5 out of 5 average rating, 19 reviews

Munster hide away

Luxurious living, fully remodeled, upgraded features and that is meticulously kept raised ranch is quiet community of Munster. This hideaway offers 4-bedrooms, King, Queen (x2), and XL Twin beds, full finished basement. Seasonal ( Midwest pool season typically July - August),access to above-ground pool, oversized back yard, and patio deck.

Guest favorite
The kitchen features dark wood cabinetry and granite countertops, with a stainless steel refrigerator and a stove integrated into the design. A cozy living area is visible, showcasing a brown leather sofa and a small table adjacent to the kitchen island.
Guesthouse in Gary
4.86 out of 5 average rating, 83 reviews

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.

Guest favorite
The exterior of the log cabin displays warm, freshly stained wood siding. A white door, framed by a small window and a light fixture, leads into the cabin. Two wooden barrels sit on the ground near the entrance, adding rustic charm to the setting.
Cabin in Griffith
4.89 out of 5 average rating, 262 reviews

Beautiful Rustic Cabin for Two!

Gorgeous newly renovated log cabin for two on a working homestead just minutes from Hard Rock Casino! Stop on in for one night or twenty nights! **IMPORTANT: MAKE SURE TO CHECK OUT THIS LISTING ON VRBO TO SAVE $20+ PER NIGHT ON YOUR BOOKING!**

Top guest favorite
A comfortable living area features a plush sectional sofa adorned with decorative pillows and a central coffee table. Natural light enters through the window covered with decorative curtains. A flat-screen TV is positioned nearby, with decorative wall art enhancing the ambiance.
Guest suite in Crete
4.91 out of 5 average rating, 252 reviews

Comfy Apt Made For Professionals or Couples

Quiet apartment perfect for working professionals and couples who would like a cozy home away from home. It has everything you would need to make your stay comfortable with a washer, dryer, full kitchen, and cable TV. Easy commute to Chicago.

Popular amenities for Highland vacation rentals

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  2. United States
  3. Indiana
  4. Lake County
  5. Highland