Vacation rentals in Highland

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Top-rated vacation rentals in Highland

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Guest favourite

Farm stay in De Motte

4.94 out of 5 average rating, 113 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.

Mar. 5 – 12

$140 CAD per night

Guest favourite

Home in Munster

4.97 out of 5 average rating, 33 reviews

Entire home: Private, Cozy Oasis in 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 3 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.

Oct. 14 – 21

$234 CAD per night

Guest favourite

Cottage in Valparaiso

4.88 out of 5 average rating, 495 reviews

Flint Lake Cottage.

This is a rustic cottage with old world charm. There are 2 fireplaces,. The home sits on a hill overlooking a lake. The lake can be accessed from the back yard. - Pet free - Earth friendly cleaning products - Private beach & park access - Easy access to city center & university - One hour from downtown Chicago - National Lakeshore and Dunes State Park nearby - Local breweries & award winning restaurants - Biking & hiking trails near by - Wood fire places to enjoy in cold weather only

Oct. 24 – 31

$220 CAD per night

Guest favourite

Home in Lansing

4.84 out of 5 average rating, 64 reviews

The Walter Experience

Come indulge in your private oasis located 35 mins from DT chicago. Ideal for Business Travelers(close to I 90/94), Couples ( Perfect Getaway ) and Small Families or friends( Relax & Replenish). Tour our town or neighboring towns ( indiana state line 2 mins away-Munster/Hammond/ Schererville -Lower taxes,Gas,etc. Local entertainment (shows or other events) Complimentary early check in may be extended. Depending on availability, Home is thoroughly cleaned and sanitized before arrival.

Aug. 11 – 18

$159 CAD per night

Guest favourite

Farm stay in Crown Point

4.91 out of 5 average rating, 106 reviews

Country vibe at Pomme Place - 3 bedroom apartment

Wind down and enjoy the country. Pomme Place, our private three bedroom apartment at Apple Blossom Trails, has a private entrance and the amenities of home. We have an apple orchard to roam, animals to watch, an adjacent playground and a great spot for bird watching. A large private deck extends from the apartment providing the perfect place to enjoy an evening. We live on site, adjacent to the apartment. We also have Paul, our musical security person, on site living in a mobile home.

Mar. 24 – 31

$220 CAD per night

Guest favourite

Cottage in Gary

4.96 out of 5 average rating, 113 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.

Nov. 7 – 14

$242 CAD per night

Guest favourite

Apartment in Hammond

4.8 out of 5 average rating, 90 reviews

Plant MOOD FREE parking, washer & dryer!

LATE CHECK-IN guest are welcome!!!! PLEASE READ MY FULL AIRBNB LISTING PRIOR TO BOOKINGS!!!! 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!

Jan. 10 – 17

$130 CAD per night

Guest favourite

Home in Munster

4.93 out of 5 average rating, 70 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.

Apr. 24 – May 1

$286 CAD per night

Guest favourite

Guest suite in Crown Point

4.93 out of 5 average rating, 208 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.

Jun. 27 – Jul. 4

$134 CAD per night

Superhost

Home in Whiting

4.8 out of 5 average rating, 225 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

Jan. 18 – 25

$166 CAD per night

Guest favourite

Cottage in Merrillville

4.89 out of 5 average rating, 183 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.

Jul. 28 – Aug. 4

$194 CAD per night

Guest favourite

Home in Gary

4.97 out of 5 average rating, 37 reviews

Private 5 Star 2 bedroom modern city farmhouse

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!

Nov. 4 – 11

$229 CAD per night

Vacation rentals for every style

Get the amount of space that is right for you.

Popular amenities for Highland vacation rentals

Kitchen

Wifi

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 vacation rentals in Highland

Superhost

Cabin in Gary

4.83 out of 5 average rating, 23 reviews

Rustic 2 bedroom cozy and quiet!

Dec. 1 – 8

$186 CAD per night

Guest favourite

Guesthouse in Merrillville

4.92 out of 5 average rating, 25 reviews

Townhouse with Jacuzzi/Sauna/fireplace

Dec. 15 – 22

$307 CAD per night

Guest favourite

Home in Munster

4.9 out of 5 average rating, 82 reviews

Cozy House with Gazebo

Jul. 31 – Aug. 7

$293 CAD per night

Guest favourite

Home in Highland

5.0 out of 5 average rating, 5 reviews

2 King 1 Queen Relaxing Spa House

Jul. 1 – 8

$495 CAD per night

Superhost

Apartment in Merrillville

4.87 out of 5 average rating, 94 reviews

Lovely 1 bed room apartment, all to yourself.

Jun. 10 – 17

$177 CAD per night

Guest favourite

Home in Crown Point

5.0 out of 5 average rating, 23 reviews

Little Pink House Downtown

Sep. 13 – 20

$277 CAD per night

Guest favourite

Home in Valparaiso

4.96 out of 5 average rating, 85 reviews

Cozy Luxe Downtown Valparaiso Stay

Aug. 29 – Sep. 5

$206 CAD per night

Guest favourite

Guest suite in Gary

4.98 out of 5 average rating, 48 reviews

Beachfront- Lake Michigan- 2bd/2bath -Heated Pool

Jan. 26 – Feb. 2

$166 CAD per night

Show all

Quick stats about vacation rentals in Highland

Total rentals
10 properties
Local attractions
Cracker Barrel Old Country Store, Wicker Memorial Park, and Strack & Van Til
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
10 properties include access to wifi
Total number of reviews
120 reviews
Nightly prices starting at
$83 CAD before taxes and fees

Vacation rentals in Highland

Top-rated vacation rentals in Highland

Farm stay in De Motte

Home in Munster

Cottage in Valparaiso

Home in Lansing

Farm stay in Crown Point

Cottage in Gary

Apartment in Hammond

Home in Munster

Guest suite in Crown Point

Home in Whiting

Cottage in Merrillville

Home in Gary

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Highland vacation rentals

Stay near Highland's top sights

Other great vacation rentals in Highland

Cabin in Gary

Guesthouse in Merrillville

Home in Munster

Home in Highland

Apartment in Merrillville

Home in Crown Point

Home in Valparaiso

Guest suite in Gary

Quick stats about vacation rentals in Highland

Total rentals

Local attractions

Popular amenities

Wifi availability

Total number of reviews

Nightly prices starting at

Destinations to explore