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.

Guest favourite

Flat 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.

12–19 Nov

₹6,702 per night
Guest favourite

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.

27 Jan – 3 Feb

₹13,403 per night
Guest favourite

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.

24–31 Jan

₹7,023 per night

Popular amenities for Highland holiday 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 holiday rentals in Highland

Guest favourite

Home in Munster

4.97 out of 5 average rating, 30 reviews

Entire home: Private, Cozy Oasis in Quiet Locale

18–25 Jan

₹10,635 per night
Guest favourite

Home in Lansing

4.83 out of 5 average rating, 59 reviews

Easter at The Walter Experience

10–17 Aug

₹8,411 per night
Guest favourite

Home in Munster

4.93 out of 5 average rating, 69 reviews

Cozy three bedroom home in Munster , Indiana.

24–31 Dec

₹14,271 per night
Guest favourite

Home in Gary

4.97 out of 5 average rating, 37 reviews

Private 5 Star 2 bedroom modern city farmhouse

10–17 May

₹10,915 per night
Superhost

Cabin in Gary

4.95 out of 5 average rating, 20 reviews

Rustic 2 bedroom cozy and quiet!

27 Jul – 3 Aug

₹10,225 per night
Superhost

Home in Munster

4.94 out of 5 average rating, 16 reviews

Happy Days

5–12 Mar

₹17,139 per night
Guest favourite

Home in Munster

4.9 out of 5 average rating, 81 reviews

Cozy House with Gazebo

26 May – 2 Jun

₹14,868 per night
Guest favourite

Home in Crown Point

5.0 out of 5 average rating, 22 reviews

Little Pink House Downtown

1–8 Aug

₹14,962 per night
Guest favourite

Home in Hammond

4.8 out of 5 average rating, 87 reviews

Spacious home 28 miles from Downtown Chicago

21–28 Jul

₹23,676 per night
Guest favourite

Home in Gary

4.88 out of 5 average rating, 40 reviews

Butterfly Bungalow near Casino, Beach & Chicago!

26 Oct – 2 Nov

₹10,978 per night
Guest favourite

Flat in Homewood

5.0 out of 5 average rating, 38 reviews

Charming Garden Apartment

14–21 Feb

₹9,078 per night
Guest favourite

Flat in Crown Point

4.95 out of 5 average rating, 62 reviews

Lovely 2 bedroom just a few blocks from the square

1–8 May

₹9,506 per night

Destinations to explore

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