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.
Apartment in Chicago
4.92 out of 5 average rating, 166 reviewsHandicap 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
Home in Portage
4.92 out of 5 average rating, 145 reviewsNewly 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
Farm stay in De Motte
4.94 out of 5 average rating, 109 reviewsCozy 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
Vacation rentals for every style
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Popular amenities for Highland vacation rentals
Other great vacation rentals in Highland
Barn in Rensselaer
5.0 out of 5 average rating, 270 reviewsThe Loft at Virgie
Nov 13 – 20
Home in Munster
4.97 out of 5 average rating, 30 reviewsEntire home: Private, Cozy Oasis in Quiet Locale
Dec 3 – 10
Home in Lansing
4.83 out of 5 average rating, 59 reviewsEaster at The Walter Experience
Aug 13 – 20
Home in Munster
4.93 out of 5 average rating, 69 reviewsCozy three bedroom home in Munster , Indiana.
Dec 24 – 31
Home in Gary
4.97 out of 5 average rating, 37 reviewsPrivate 5 Star 2 bedroom modern city farmhouse
Feb 5 – 12
Cabin in Gary
4.95 out of 5 average rating, 20 reviewsRustic 2 bedroom cozy and quiet!
Nov 5 – 12
Home in Munster
4.94 out of 5 average rating, 16 reviewsHappy Days
Jul 30 – Aug 6
Home in Gary
4.88 out of 5 average rating, 40 reviewsButterfly Bungalow near Casino, Beach & Chicago!
May 28 – Jun 4
Home in Munster
4.9 out of 5 average rating, 81 reviewsCozy House with Gazebo
Dec 11 – 18
Home in Crown Point
5.0 out of 5 average rating, 22 reviewsLittle Pink House Downtown
Jul 31 – Aug 7
Home in Merrillville
5.0 out of 5 average rating, 16 reviewsCreekside Getaway
Aug 3 – 10
Home in Hammond
4.8 out of 5 average rating, 87 reviewsSpacious home 28 miles from Downtown Chicago
Sep 5 – 12
Destinations to explore
- Downtown Chicago Vacation rentals
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