Holiday rentals in Highland

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.

Entire home: Private, Cozy Oasis in a 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 2 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.

EC Indiana’s Peaceful Turquoise Experience

Come relax in this newly remodeled different shades of turquoise apartment🙌🏼🙏🏼🙌🏼 In Indiana near Hammond, in a nice quiet area right next to a park that has workout equipment, it’s near a beach, local highways, a very large YMCA, restaurant’s, metra station & shopping centers. It is minutes away from 3 nearby Indiana casinos and just 25 minutes from downtown Chicago. This place is great for work or traveling professionals, romantic get aways, out of town guest, family and friends

Neon Dunes Vista Beachfront Cottage

Neon Dunes Cottage is a one bedroom 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.

Cozy Stays

Kick back and relax in this calm, stylish, 2bdrm apartment located just 25 minutes outside of Chicago. It’s on the 1st floor. . A very quiet community. Secured gated parking, Very convenient ‼️ Parking just steps away from the main door entry. Surrounded by nice restaurants, shopping centers, movie theaters, and workout facilities . A MUST SEE‼️ come savor the experience of a dwelling that feels very personal to your very own home. PRIVACY & CLEANSINESS IS TOP PRIORITY.

Lovely 1-BR Apt with full kitchen & living room

Kick back and relax in this calm, stylish space. We’re super excited to have you as our guest. This apartment is located on the 2nd floor (entrance from outside stairs). We are 30 minutes away from Downtown (no traffic), 4 minutes from Chicago Skyway and 11 minutes from Interstate 94. Enter your space through your own private entrance and make yourself at home. Your unit includes a private 1 Bedroom, 1 Bathroom, a Kitchen, Living Area with a sleeper sofa and desk.

Cozy Corner, Apartment 2S. Steps to shops & Dining

Located just steps from downtown Valparaiso, this historic upstairs apartment has been fully restored and updated! You'll find restaurants, local shops, and breweries/wineries just minutes away. Whether you want to cook a meal in the kitchen, roast a s'more above the (shared) firepit in the backyard, or venture downtown, you'll never find a shortage of things to do. This is the perfect getaway for up to 4 people who want to relax or adventure in Northwest Indiana!

Plant MOOD FREE Wi-fi, 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!

Laurna Dune

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!

Townhome Near Munster/Hospital/BP Refinery

Duplex Home near the South Shore Line for a quick and easy commute to Chicago or close to all the hospitals and BP refinery. This place is intended for the corporate traveler. 30 night minimum stay required. Detached 2 car garage, fenced in yard, close to all the local restaurants and shopping, bike trail and park within walking distance.

Beautiful Rustic Cabin for Two!

Gorgeous newly renovated log cabin for two on a working homestead just minutes from Hard Rock Casino! Stop on in for one night or twenty nights! **IMPORTANT: MAKE SURE TO CHECK OUT THIS LISTING ON VRBO TO SAVE $20+ PER NIGHT ON YOUR BOOKING!**

Comfy Apt Made For Professionals or Couples

Quiet apartment perfect for working professionals and couples who would like a cozy home away from home. It has everything you would need to make your stay comfortable with a washer, dryer, full kitchen, and cable TV. Easy commute to Chicago.