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.

Guest favorite

Apartment in Chicago

4.92 out of 5 average rating, 166 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.

Aug 16 – 23

G$22,496 GYD per night
Guest favorite

Home in Portage

4.92 out of 5 average rating, 145 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.

Jan 18 – 25

G$33,669 GYD per night
Guest favorite

Farm stay in De Motte

4.94 out of 5 average rating, 109 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.

Sep 26 – Oct 3

G$17,643 GYD per night

Popular amenities for Highland vacation rentals

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 vacation rentals in Highland

Guest favorite

Barn in Rensselaer

5.0 out of 5 average rating, 270 reviews

The Loft at Virgie

Nov 13 – 20

G$31,156 GYD per night
Guest favorite

Home in Munster

4.97 out of 5 average rating, 30 reviews

Entire home: Private, Cozy Oasis in Quiet Locale

Dec 3 – 10

G$26,715 GYD per night
Guest favorite

Home in Lansing

4.83 out of 5 average rating, 59 reviews

Easter at The Walter Experience

Aug 13 – 20

G$21,129 GYD per night
Guest favorite

Home in Munster

4.93 out of 5 average rating, 69 reviews

Cozy three bedroom home in Munster , Indiana.

Dec 24 – 31

G$35,849 GYD per night
Guest favorite

Home in Gary

4.97 out of 5 average rating, 37 reviews

Private 5 Star 2 bedroom modern city farmhouse

Feb 5 – 12

G$27,417 GYD per night
Superhost

Cabin in Gary

4.95 out of 5 average rating, 20 reviews

Rustic 2 bedroom cozy and quiet!

Nov 5 – 12

G$26,334 GYD per night
Superhost

Home in Munster

4.94 out of 5 average rating, 16 reviews

Happy Days

Jul 30 – Aug 6

G$48,071 GYD per night
Guest favorite

Home in Gary

4.88 out of 5 average rating, 40 reviews

Butterfly Bungalow near Casino, Beach & Chicago!

May 28 – Jun 4

G$19,483 GYD per night
Guest favorite

Home in Munster

4.9 out of 5 average rating, 81 reviews

Cozy House with Gazebo

Dec 11 – 18

G$36,886 GYD per night
Guest favorite

Home in Crown Point

5.0 out of 5 average rating, 22 reviews

Little Pink House Downtown

Jul 31 – Aug 7

G$37,585 GYD per night
Guest favorite

Home in Merrillville

5.0 out of 5 average rating, 16 reviews

Creekside Getaway

Aug 3 – 10

G$31,324 GYD per night
Guest favorite

Home in Hammond

4.8 out of 5 average rating, 87 reviews

Spacious home 28 miles from Downtown Chicago

Sep 5 – 12

G$59,473 GYD per night

Destinations to explore

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  4. Lake County
  5. Highland