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

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.

Flat in Hammond

4.85 out of 5 average rating, 167 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 favourite

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, 108 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.

Guest favourite

A vibrant garden area is filled with a variety of lush green plants and colorful flowers. Stone elements lead to a small water feature, surrounded by dense foliage. The peaceful setting offers a natural retreat, inviting exploration or relaxation.

Flat in Homewood

4.92 out of 5 average rating, 100 reviews

Charming Garden Apartment

Make yourself at home in a charming apartment with all the amenities! Lose yourself birding or reading a book surrounded by lush gardens. Take a short walk to downtown Homewood to enjoy shopping & dining or catch the train to Chicago. 🏳️‍🌈 BLM Safe space! After a day of exploring, a king-sized sleep number bed & lush bathroom features will pamper you! A fold-down sofa creates an additional bed. Dogs welcome! This suite has a kitchenette with a convection toaster oven & induction cooktop.

Top guest favourite

A modern farmhouse is showcased, featuring a covered front porch with comfortable seating. Lush greenery surrounds the entrance and a small outdoor seating area with a table and chairs is visible. The structure is complemented by large windows that invite natural light.

Home in Crown Point

4.96 out of 5 average rating, 93 reviews

Quiet Farmhouse Retreat

Looking for a tranquil farmhouse destination? Get away at Wadsworth Acres- a Scottish Highland hobby farm! This modern farmhouse is the perfect space to relax. Complete with a very spacious primary suite, large eat-in kitchen, exercise room, and space to play outside- you’ll never have to leave! Enjoy your morning coffee with breathtaking farm sunrises on the patio and evenings in the hammocks.Peaceful escape just 5 minutes from the highway, 10 from historical downtown, 35 from the Dunes!

Top guest favourite

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, 213 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 favourite

An open-concept living area showcases a dark leather sofa and recliner, complemented by a green coffee table. The kitchen features dark cabinetry and stainless steel appliances. A bookshelf stands against the wall, and natural light is provided by large windows with light curtains.

Home in Schererville

4.93 out of 5 average rating, 69 reviews

Luxury Home in Schererville-garage use included!

Located close to downtown, this spacious, new-construction, family-friendly home is the perfect getaway! Near unique shops, parks, restaurants, and local activities, there is plenty to do and see! A 45 minute drive to Chicago or a 45 minute drive to the beautiful beaches of Lake Michigan will add more fun things to do while visiting. Enjoy the comforts of modern living with a spacious 3-bedroom, 2.5 bath, 2-story home with numerous amenities and features.

Guest favourite

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 favourite

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, 123 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

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, 259 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.

Top guest favourite

A well-maintained exterior view of the cottage is displayed, featuring a neatly manicured lawn and bordered by trees. A private driveway leads to the entrance. The structure showcases a front porch area, and a fire pit is visible in the yard, inviting outdoor enjoyment.

Cottage in Merrillville

4.88 out of 5 average rating, 274 reviews

The Hideaway-An experience getaway!

NEW: Sauna & Jacuzzi! Welcome to your cozy cottage ESCAPE, a modern sanctuary 30 minutes from Chicago. This secluded private, detached cottage on a 3-acre property features a NEW SAUNA with Bluetooth & light therapy & JACUZZI (outdoor w/ privacy walls, a king-size bed, and a full kitchen. Enjoy your own yard, fire pit, and covered parking. A perfect blend of comfort and convenience. Single, or couples only.

Superhost

An entrance porch features a welcome sign above the door. Two folding chairs are positioned on a wooden floor, accompanied by a small table with a bowl of fruit. Soft white drapes frame one side, and outdoor string lights add a warm touch.

Home in Gary

4.84 out of 5 average rating, 95 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!

Superhost

Apartment in Lynwood

5 out of 5 average rating, 3 reviews

Luxury Modern Condo - Suburban Escape

Enjoy a luxury modern condo just 20 minutes from Chicago! Perfect for short-term stays or business travel, this stylish suburban retreat features 3 bedrooms, 2 full bathrooms, a full kitchen, TV, high-speed Wi-Fi, and in-unit laundry. Relax in a quiet neighborhood with free parking and quick city access — ideal for comfort, convenience, and productivity.