Holiday rentals in Hobart

Trailside Retreat

Welcome to Trailside Retreat, your ideal getaway. Our spacious, open-concept 1,000 square ft. apartment located behind the main house has complete privacy. It has two bedrooms—one with a king-size bed and another with two full beds, plus a full-size hide-a-bed in the living room. It includes a fully equipped kitchen with open dining area. And the living room area is perfect for game nights, movie marathons or a romantic dinner for two. Enjoy your private patio and beautifully landscaped yard.

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.

Downtown Apartment on Lincolnway

Convenience at its best meets historic charm! Located in the center of downtown Valparaiso (literally), The Lincoln is in a prime location that puts you within minutes to enjoy all that downtown Valparaiso and the surrounding areas have to offer. Walk to fabulous restaurants, local boutique shops, bars, breweries, wineries, and distillery in minutes. Downtown Valpo offers numerous exciting events throughout the year. The Lincoln is perfect for families & friends who want to relax or adventure!

ValpoVilla: Location, location, location!

Located in the heart of downtown Valparaiso, guests will love this updated, historic charmer! Walk to fabulous restaurants, local shops, or breweries & wineries in minutes. This unit has been fully updated and fully stocked with room to sleep 6. You'll be 25 minutes from the beaches of Lake Michigan/Indiana Dunes National Park, an hour from Chicago, and close to quaint towns and apple/berry picking orchards. This space is perfect for families & friends who want to relax or adventure outdoors!

Creekside Getaway

Take it easy at this unique and tranquil getaway. Located in a wooded cul-de-sac, privacy and nature abound. The home is also situated on a deer path. Watch families of deer migrate to the east in the morning and return West in the early evening. Blue Heron fish in the backyard creek. The creek is also used for kayaking to Lake George in Hobart. Try your hand at fishing. Blue gill, crappy and carp have been caught from those waters. Service dogs will be charged $ 75.00 cleaning fee.

Indiana Dunes, Beach, Chicago, Shopping Center

Near Indiana Dunes, Lake Michigan and Chicago when you stay at our centrally-located townhome. For family fun we’re is located a few minutes away from the shopping center, plenty of restaurants, main chain stores and more. Enjoy the convenience a parking garage& driveway, outdoor patio, dishwasher and washer & dryer. home has 4 beds 2 bedrooms. One bedroom has a Queen bed, second bedroom has a Queen bed and a Full bed. The Living room has a sofa bed. Shovel in the garage for when it snows.

Updated Home with Fenced Backyard, sleeps 10

Your family will enjoy this centrally-located home within walking distance of downtown, close to VU as well as the new Journeyman Distillery. Our home is perfect for a large family or wedding party, as it has 4 beds and can comfortably sleep up to 10 guests using the pullout couch. The home includes stainless steel appliances and a private fenced yard. With 2 bathrooms, a double vanity, and a half bath, there's room for everyone to get ready. We hope you enjoy your journey to Valpo!

The Ambrose Suite - Guesthouse in Valparaiso

Stay at the historic Elmer Wolf House, also known as the Wolf Manor, built in 1890. This luxe suite features pristine antique furnishings with refined elegance on 4.8 peaceful acres with gardens, birdwatching, and multiple outdoor spaces. Enjoy hammocks, fire pit, and a stone picnic area. Just 6 miles to downtown Valparaiso and 15 minutes to the Dunes National Park. Private entrance, carriage house parking, full kitchen, queen bedroom, bath, and laundry.

The Jefferson House

Enjoy a stay in our charming, newly renovated three-bedroom home in downtown Valparaiso! The Jefferson House is perfect for those looking to explore Northwest Indiana and its surrounding area. It's close to state and national parks, universities, and big cities like Chicago and Indy—while maintaining that small-town charm. You will enjoy our local restaurants, wineries, breweries, cafes/coffee roasters, and shops in Valparaiso's vibrant downtown.

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.

Flint Lake Cottage.

This is a rustic cottage with old world charm. There are 2 fireplaces,. The home sits on a hill overlooking the channel that leads to Flint Lake. - Pet free -May not be appropriate for people with mobility issues. - 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 - Wood fireplaces (winter only!)

The Good Farm: Barn BnB on 44 acres near Lake Mich

Escape to BarnBnB, a charming barn apartment on 44 acres just 15 minutes from Lake Michigan beaches and Indiana Dunes National Park. 🐓🌳 Perfect for families or groups (up to 6 guests), this peaceful retreat blends modern comforts with farm life—free-range chickens, firepit evenings, and trails included. Relax in nature or explore nearby Valparaiso, Chesterton, and Michigan City for the perfect mix of adventure and tranquility.