Holiday houses in Highland

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Highland

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

0 of 0 items showing

1 of 3 pages

Guest favourite

Farm stay in La Porte

4.99 out of 5 average rating, 443 reviews

Cabin on Swede Hill

Welcome to "Cabin on Swede Hill". Our family has farmed this land since 1871. My great grandparents, Swan and Johanna Johnson immigrated to America in the 1860's, found this land which was similar to Sweden. They raised their family here. Approximately 65 Swedish families settled in this community, became to be know as the "Swede Hills". We just received the Hoosier Homestead Award from Indiana celebrating the Sesquicentennial Award. We invite you to come...... and experience country life.

Guest favourite

Apartment in Chicago

4.91 out of 5 average rating, 170 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 Portage

4.92 out of 5 average rating, 151 reviews

Newly Renovated with Finished Basement

This beautiful house is located near Lake Michigan in Northwest Indiana, less than 10 minutes from the expressway and toll road. There is a stainless steel kitchen, spa bathroom, finished basement and bar with sleeping capacity to accommodate two families. This is a smart home with Ring db, lights and thermostat controlled by your voice. We are less than an hour drive from downtown Chicago, and there are many great beaches nearby. Shopping and great dining options are also within a close drive.

Guest favourite

Farm stay in De Motte

4.94 out of 5 average rating, 114 reviews

Cozy barn loft on organic vegetable farm

Find peace and restoration in this beautiful barn loft at Perkins' Good Earth Farm. The loft has a bedroom, separate shower and toilet spaces, work area, sitting room, kitchen space, and heating/cooling fresh air system. Located above our farm store, the loft provides privacy for you while giving you access to fresh fruits & veggies, locally sourced meats, homemade soups & salads from our farm kitchen, and so much more. You can also walk our farm trails, visit the veggies, or enjoy a campfire.

Guest favourite

Apartment in Chebanse

4.96 out of 5 average rating, 485 reviews

Cathy's Little Farm Loft

Cathy's Little Farm loft is a new 500 sq ft apartment inside a storage barn on a wooded country acre. Fully appointed two story space offers peace and quiet. It is located close to I57, Walmart, Community College, Airport, Fair Grounds, National Guard Training Center, 15 minutes from Olivet, 60 miles south of Chicago. King size bed and twin size sofa sleeper upstairs, full size sleeper sofa in living room. Well equipped full size kitchen and laundry. Large lawn and garden area to enjoy.

Guest favourite

Cottage in Gary

4.97 out of 5 average rating, 118 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

Barn in Rensselaer

5.0 out of 5 average rating, 281 reviews

The Loft at Virgie

You don't have to be born in a barn to vacation in one. Trade in the city for millions of stars in the night sky! As you enter thru the French doors you will be greeted by an open concept room decorated with a barn/industrial motif. Knotty pine car-siding and galvanized steel, wood floors along with a reclining leather couch and love seat fill the room A full kitchen with granite counter tops await you. There is plenty of natural lighting for the evenings.

Guest favourite

Home in De Motte

4.95 out of 5 average rating, 211 reviews

Country Cottage

Looking for week-end get away? Traveling through Northwest Indiana on I-65 and looking for a quiet place to stay for the night? Situated on 6 acres and with convenient (2 mile) access to I-65, our cozy Country Cottage is a great choice! Enjoy the cottage feel of this recently renovated (new cabinets, flooring, appliances) and charmingly decorated home, located in close proximity to local attractions! Our 650 square foot cottage is ideal for 1 - 4 guests.

Guest favourite

Guest suite in Crown Point

4.93 out of 5 average rating, 209 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.

Superhost

Home in Whiting

4.8 out of 5 average rating, 227 reviews

Whiting Getaway

Nicely situated in the quiet and safe city of Whiting IN, near the bustling Whihala Beach on Lake Michigan, just down the street from Wolfe Lake and the Wolfe Lake Pavilion, within 2 miles of The Horseshoe Casino and just 20 minutes (17.5 miles) from downtown Chicago, this house offers a perfect location for a complete vacation. Come and enjoy all that the 'region' has to offer

Guest favourite

Cottage in Merrillville

4.89 out of 5 average rating, 188 reviews

The Hideaway

This cozy cottage (lodging only, renters only) located 30 minutes from Chicago is located on a private 3 acre property. It’s a private detached cottage that sleeps four. One king size bedroom (sheets supplied), large full bathroom with deep tub (towels supplied), full kitchen (dishes, pots and pans ect supplied) and private parking. Also has its own fire pit for enjoyment.

Guest favourite

Home in Cedar Lake

4.85 out of 5 average rating, 213 reviews

Vacation home on south end of Cedar Lake

Private two story fully furnished older vacation home on the south side of cedar lake. Both bedrooms and half bath are upstairs. Main level has living room/dining room combo, kitchen and full bath. Short drive to marinas with kayak/boat rentals, public beach and boat launches. Within walking distance is a bar/restaurant with kayak rental.

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Highland holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Stay near Highland's top sights

Cracker Barrel Old Country Store3 locals recommend

Langel's Pizza4 locals recommend

Sip Coffee House and Artisan Cafe3 locals recommend

Other great holiday rentals in Highland

Guest favourite

Home in Munster

4.95 out of 5 average rating, 38 reviews

Entire home: Private, Cozy Oasis in Quiet Locale

Superhost

Apartment in Hammond

4.81 out of 5 average rating, 94 reviews

Plant MOOD FREE parking, washer & dryer!

Guest favourite

Home in Lansing

4.8 out of 5 average rating, 66 reviews

The Walter Experience

Guest favourite

Home in Gary

4.95 out of 5 average rating, 41 reviews

Private 5 Star 2 bedroom modern city farmhouse

Guest favourite

Home in Munster

4.93 out of 5 average rating, 71 reviews

Cozy three bedroom home in Munster , Indiana.

Guest favourite

Home in Munster

4.91 out of 5 average rating, 86 reviews

Cozy House with Gazebo

Guest favourite

Home in Highland

5.0 out of 5 average rating, 6 reviews

2 King 1 Queen Relaxing Spa House

Guest favourite

Loft in Crown Point

4.97 out of 5 average rating, 63 reviews

Liz's Loft - 1 bedroom loft on 4 acres!

Show all

Quick stats about accommodation in Highland

Total rentals
10 properties
Local attractions
Cracker Barrel Old Country Store, Wicker Memorial Park and Strack & Van Til
Popular amenities
Kitchen, Wi-Fi and Pool
Wi-Fi availability
10 properties include access to Wi-Fi
Total number of reviews
120 reviews
Nightly prices starting at
$91 AUD before taxes and fees

Holiday houses in Highland

Top-rated holiday rentals in Highland

Farm stay in La Porte

Apartment in Chicago

Home in Portage

Farm stay in De Motte

Apartment in Chebanse

Cottage in Gary

Barn in Rensselaer

Home in De Motte

Guest suite in Crown Point

Home in Whiting

Cottage in Merrillville

Home in Cedar Lake

Holiday rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Highland holiday rentals

Stay near Highland's top sights

Other great holiday rentals in Highland

Home in Munster

Apartment in Hammond

Home in Lansing

Home in Gary

Home in Munster

Home in Munster

Home in Highland

Loft in Crown Point

Quick stats about accommodation in Highland

Total rentals

Local attractions

Popular amenities

Wi-Fi availability

Total number of reviews

Nightly prices starting at

Destinations to explore